Kendall Jenner & Devin Booker Relationship Timeline

For years, fans all over the world have been keenly interested in the romantic journey of Kendall Jenner and Devin Booker. Admittedly, Jenner has always preferred to keep her romantic life private. Speaking with Vogue Australia in 2019, the then-24-year-old model shared that “a relationship is only meant to be between two people.” 

However, to the joy of many fans, she’s not been completely secretive about her love life. Since 2020, Jenner and Booker have been romantically entangled. However, their relationship was on-and-off as it hit some hitches along the way. They were recently seen in the same VIP suite at the Super Bowl, prompting rumors of them rekindling their relationship. While they are no longer together, their romance is still fresh in the minds of some onlookers. Here’s a timeline of their relationship.

Read More: Bad Bunny Spotted Rocking Kendall Jenner’s Necklace

2018: Kendall Jenner And Devin Booker Meet

While they may have met earlier, the first time this pair was spotted together was in 2018. Interestingly, it was at a double date that Jenner and Booker attended with different people. At the time, Jenner was reportedly in a relationship with basketball player Ben Simmons who was her date for the night. Also taken, Booker attended the double date with his girlfriend at the time, Jordyn Woods, Jenner’s younger sister Kylie’s then-best friend.

April 2020: Road Trippin’

After their double date in 2018, Jenner and Booker were not spotted together again until April 2020. The two were seen together at a rest stop during a road trip to Sedona, Arizona. At the time, much had changed as they were no longer with their partners of 2018. Also, following a cheating scandal involving Jordyn Woods and Tristan Thompson, Jenner and Woods stopped being friends. While Jenner and Booker being seen together raised eyebrows, a source told PEOPLE that the two weren’t dating.

Read More: Kendall Jenner’s Versace Runway Walk Slammed By Fans: See Reactions

August — December 2020: More Public Sightings

Subsequently, rumors and speculations of a relationship intensified. This was because Kendall Jenner and Devin Booker were repeatedly sighted together throughout the rest of 2020. For example, in August, they went to dinner at Nobu restaurant in Malibu, California, with Kylie Jenner. Also, in September, Jenner and Booker went on a fancy lake vacation with Justin and Hailey Bieber. Furthermore, in October, they attended Kim Kardashian’s 40th birthday party together. While all of this happened, fans were beside themselves with excitement, and some were completely convinced that the two were already a couple. However, an official confirmation of a relationship never came in 2020.

February 2021: Kendall Jenner And Devin Booker Become Official 

As the month of love rolled in, the two decided to quench the thirst of many curious fans. On Valentine’s Day, 2021, Jenner and Booker officially announced their relationship via Instagram. They both posted cute photos, and each opted to use a simple but profound heart emoji as the caption. Although there were no words written, the couple’s photos and captions said enough. Viewers certainly got the message.

June 2021: The Couple Celebrate Their One-Year Anniversary 

After about four months of going public, Kendall Jenner and Devin Booker celebrated their first anniversary on June 12, 2021. The social media posts they shared made fans realize that they had actually started dating back in 2020. Evidently, although the couple did not confirm the rumors back then, fans were right about their secret romance. 

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Read More: Devin Booker & Kendall Jenner Call It Quits

July — December 2021: More Cute Relationship Shenanigans 

Kendall Jenner and Devin Booker
LOS ANGELES, CA – OCTOBER 22: Kendall Jenner and Devin Booker #1 of the Phoenix Suns kiss and hug after the Suns defeated the Los Angeles Lakers, 115-110, at Staples Center on October 22, 2021 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)

Throughout 2021, Kendall Jenner and Devin Booker gave fans cute glimpses into their romantic life. While they were still mostly private, they showed the public enough to let them know that they were very utterly smitten. When Booker made it to the NBA finals with the Phoenix Suns in July, Jenner was there, cheering him on. During an Italian getaway in August, the two were spotted being adorable together. Also, on Jenner’s birthday in November, the basketball player proudly gushed about his girlfriend on Instagram. He posted several photos of Jenner on his Instagram story, one of which he captioned “Most beautiful woman.”

January — May 2022: The Storybook Romance Continues

In 2022, the couple’s romantic flame continued to burn brightly, and they let fans in on it. In January, the KUWTK star shared photos of a weekend holiday with Booker. Later, the couple attended the Super Bowl together in February, and sat with the Biebers. When Booker was asked about his relationship with Jenner during an interview with Wall Street Journal in March, he said he was “enjoying life to the fullest.” Another notable point in their relationship was when Jenner brought Booker as her date to Kourtney Kardashian’s wedding in May 2022.

June — September 2022: The Two Reportedly Break Up And Get Back Together 

kylie jenner devin booker
PORTOFINO, ITALY – MAY 21: Kendall Jenner and Devin Booker arriving for lunch at the Abbey of San Fruttuoso on May 21, 2022 in Portofino, Italy. (Photo by NINO/GC Images)

In June 2022, multiple sources shared with Entertainment Tonight that Kendall Jenner and Devin Booker had broken up. According to Entertainment Tonight, one source said that the two “have had discussions about their future but they are not on the same page.” Another source shared, “Kendall feels they’re on different paths.” However, later in June 2022, the two were spotted together at Soho House in Malibu. Subsequently, they were seen together a few more times between July and September. For example, paparazzi caught them heading out for a date night in August, and spending a weekend together in NYC in September. 

November 2022: Sources Confirm That The Two Have Broken Up

While it seemed like the couple was back on track after they reportedly broke up in June, it unfortunately didn’t last very long. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” one source told PEOPLE. Another source told Us Weekly that the pair broke up a month prior and that “things are amicable after the breakup, there’s no bad blood between them.”

2023: The Aftermath

kylie jenner devin booker
NEW YORK, NEW YORK – MAY 01: Bad Bunny and Kendall Jenner attend The After hosted by Diddy & Doja Cat powered by Ciroc Premium Vodka and DeLeon Tequila at Club Love on May 01, 2023 in New York City. (Photo by Shareif Ziyadat/Getty Images)

Following their breakup, Kendall Jenner got into a relationship with Bad Bunny in early 2023. Subsequently, in April 2023, a source told Us Weekly that Booker wasn’t completely over Jenner just yet. “Devin doesn’t believe for one minute that Kendall and Bad Bunny’s relationship is that serious,” the source said. “He doesn’t think he’s her type and finds it difficult to believe there’s any longevity there between them.”

February 2024: Something Brewing?

kylie jenner devin booker
Kendall Jenner and Devin Booker at the Marni Spring 2023 ready to wear runway show front row on September 10, 2022 in Brooklyn, New York. (Photo by Fairchild Archive/WWD via Getty Images)

Booker’s alleged interest in getting back together with Kendall certainly excited some fans. However, if it was true, nothing ever came of it. While the two seem to have no ill feelings toward each other, they have mostly kept their distance since they broke up in 2022. Their 2024 sighting was at the Super Bowl where they happened to be in the same $1 million VIP suite. However, they did not sit together. Through a series of photos posted by Kylie Rubin (daughter of Fanatics CEO, Michael Rubin), fans noticed that Rubin was in the same suite as Jenner and Booker.

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Usher & Jennifer Goicoechea: Relationship Timeline

In the blink of an eye, Jennifer Goicoechea became Usher’s wife. The R&B icon and the talented music executive have been turning heads with their love this year. And now, they’ve taken it a step further with their recently announced wedding. They exchanged vows after Usher’s amazing Super Bowl Halftime performance. Evidently, these two are madly in love, and Usher’s swooning confessions even made it to his ninth album, Coming Home. As the pair are now on their next phase as a couple, let’s journey through Usher and his wife, Jennifer Goicoechea’s relationship timeline.  

Read More: Who Has Usher Dated?

2016-2019: Love In & Outside Of The Club

 
 
 
 
 
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A post shared by Jennifer Goicoechea Raymond (@boogsneffect)

While it is unknown when the two first met, Usher and Goicoechea were first photographed together in 2016. The next time they were seen together was two years later. Goicoechea posted a photo on Instagram, which featured her positioned between two friends, and Usher laughing as he leaned over the trio. The photo immediately sparked dating rumors, especially since Goicoechea seemed to be quite close to Usher and his close circle of friends. Usher and his now-wife eventually came out and confirmed the rumors in 2019. While attending the Hollywood Bowl, the two shared a photo with Goicoechea kissing Usher on the cheek.  

2020-2021: Becoming Parents

 
 
 
 
 
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A post shared by Usher (@usher)

By 2020, the couple was revealed to be expecting their first child together. The pair was spotted in Los Angeles, outside a production studio, showcasing Jennifer’s visible baby bump. A source speaking with Us Weekly shared that the couple was “thrilled and very excited.” A few months later, the couple welcomed their baby girl, Sovereign Bo Raymond. 

In May 2021, Usher revealed that he and his now-wife were expecting their second child together. By September, Sire Castrello Raymond was born. Usher gushed about the baby on his Instagram and posted a close-up of Sire’s face with the caption: “Hi, my name is Sire Castrello Raymond. I am the newest addition to the Raymond crew. I was born Sept 29 2021 at 6:42pm weighing 7lbs 13oz. Hear me roar … A.K.A Ra Ra. Gang.”

Read More: Usher 2024 Tour: Dates, Tickets & More

2023: Gushing Over Love

Even before she became his wife, Usher regularly posted Goicoechea on his Instagram account, from Mother’s Day celebrations to Halloween. In November 2023, Usher gushed about his love and relationship with Goicoechea to PEOPLE Magazine. “I have an amazing partner, a support system,” he said. He rounded out the interview by revealing that he’s “very happy, very fortunate to have an incredible friend, not just a partner. She’s my best friend and I love her.”

2024: Usher And Jenn Become Husband And Wife

Usher and Goicoechea obtained a marriage license in Nevada a few days before the Super Bowl. After giving a phenomenal performance at the Super Bowl Halftime, the eight-time Grammy winner went off and tied the knot with his love. Usher also took to his Instagram to post various pictures of the wedding. The intimate moment also featured Usher and Jenn’s kids, as well as his children with his ex-wife, Tameka Foster.   

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50 Cent & Jamira “Cuban Link” Haines: Relationship Timeline

The romance between rapper and entrepreneur 50 Cent and his girlfriend Jamira “Cuban Link” Haines has been quite interesting. Most especially because the rapper’s been much more public than he’s ever been before. As the duo ventured into the public eye, their relationship became a fun and memorable saga; from their first hints of love to TikTok videos. However, following his New Year’s pledge to practice abstinence, many are wondering if 50 Cent and his girlfriend are still an item. Let’s delve into the captivating timeline of their relationship. 

Read More: Cuban Link Exposes What It’s Really Like To Date 50 Cent

2019: Whispers Of Love

50 cent girlfriend jamira cuban link haines
NEW YORK, NEW YORK – AUGUST 20: Curtis James Jackson III (L) and Jamira attend the “Power” final season world premiere at The Hulu Theater at Madison Square Garden on August 20, 2019 in New York City. (Photo by Monica Schipper/WireImage)

The public first caught wind of 50 Cent and his girlfriend, Jamira Haines relationship in 2019. The relationship was hinted at on social media posts, and fans were quite surprised by it. This is due to 50 Cent’s preference for staying private about his relationships. At the time, Haines was 25 years old while 50 Cent was 44. While it is unknown when the two first met or started dating, the couple shockingly went on Instagram Live and shared how their first date went. The rapper said: “The first time I went to meet her, she gave me an address and it was the restaurant.”

Haines jokingly replied, “I had to make sure you were like … real. You wasn’t coming to my house.” By August, the couple made their public red carpet-debut. 50 Cent and his girlfriend attended the season 6 premiere of Power. After Haines posted a few pictures of them together on her social media, fans showered them with love and supported their relationship.

2020: Break-Up Rumors

50 cent girlfriend jamira cuban link haines
HOLLYWOOD, CALIFORNIA – JANUARY 30: (L-R) Curtis “50 Cent” Jackson and Jamira Haines pose during a ceremony honoring 50 Cent with a star on the Hollywood Walk of Fame on January 30, 2020 in Hollywood, California. (Photo by Leon Bennett/Getty Images)

In January 2020, Haines accompanied 50 Cent as he received the prestigious star on the renowned Hollywood Walk of Fame. Later that year, the couple were rumored to have broken up when most of the pictures and videos of 50 Cent on Haines’ Instagram were deleted. It was an abrupt change that many fans noticed, and subsequently, break-up rumors began circulating. Haines later posted pictures of her in her apartment with the caption: “Haven’t been in my apartment in forever.” This further fueled the rumors that 50 Cent and his girlfriend were no longer an item. However, the chatter proved false, as the two soon posted pictures together. 

2021-2023: Public Affections

50 Cent and his girlfriend continued to share their love for each other on their social media accounts, especially TikTok. They famously pranked and poked fun at each other, and it was evident they were happy. By January 2023, they made a rare public appearance at the season 2 premiere of BMF in Los Angeles. In April, Haines shared a video on Instagram attending a 50 Cent concert. Observant fans couldn’t help but notice a sizable rock adorning her ring finger, igniting speculation and rumors about a potential engagement. This also came as no surprise because the rapper had expressed his interest in getting married. However, the rumor was quickly debunked by TMZ, who stated that Haines had worn the ring several times before.

Read More: 50 Cent Shuts Down Cuban Link Engagement Rumors

2024: Broken Up, Or Staying Private?

 
 
 
 
 
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A post shared by 50 Cent (@50cent)

The onset of the New Year seems to have brought about a potential shift in 50 Cent’s relationship with his girlfriend. The “Candy Shop” rapper revealed his commitment to “practicing abstinence” as a resolution of his. “My new idea is so big, I don’t have time to be distracted,” he wrote. “I’m practicing abstinence. I have been meditating and focusing on my goals. I hope this New Year helps you excel to the next level.”

Adding to the intrigue, there’s a noticeable absence of any photos featuring 50 Cent and his girlfriend. Concurrently, the former model and social media influencer did share a cryptic message about embracing changes in life and relationships. This has once again fueled speculation that they’re split. However, nothing’s been confirmed, and they could simply be continuing their relationship on the low.  

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Jacquees & Dreezy: Revisiting Their Relationship Timeline

Among the many celebrity love stories making waves currently, the relationship between Jacquees and Dreezy has particularly caught the attention of many. The two artists, each carving their paths in the music industry, shared a unique love. However, after some hitches, they called it quits. This is why rumors of a reconciliation are currently shocking their respective fans. Specifically, Dreezy and Jacquees’s girlfriend, Deiondra Sanders, have been beefing on social media. As a result, some interesting allegations have been coming to light. Nonetheless, let’s unravel the melodies of love and collaboration that defined the entwined journey of Jacquees and Dreezy.

2018 – Early 2019: Jacquees & Dreezy Begin Dating  

Jacquees, born Rodriguez Jacquees Broadnax, and Dreezy, born Seandrea Sledge, burst onto the scene due to their musical talents. Both artists met in 2018 on tour, and while everyone else saw a working relationship, romance was blooming between the two. Therefore, it didn’t take long before they started dating. However, before the public announcements, Dreezy featured Jacquees on her sultry single, “Love Someone.” Soon after, they confirmed their relationship. 

As if to announce their relationship loud and clear for everyone, Jacquees and Dreezy spent Valentine’s Day together. Jacquees planned an extraordinary surprise for his girlfriend, orchestrating a romantic evening filled with thoughtful gestures. He also booked her a flight to Houston, then personally whisked her to a beautifully adorned condo. Furthermore, the couple had a lavish dinner right before he gifted her a Chanel purse and slides. To crown it all, he also gave her a puppy, which she named Chanel.

The next month, Dreezy gushed about her relationship with Jacquees during an interview with Rap-Up. She gave a run-through of how they spent Valentine’s Day and what the singer is like in private. “He’s more than what y’all see on the internet…” she said. “To kinda step around his world and his career and see how he handles it, I got nothing but respect for it.”

Late 2019 & Early 2020: Breaking Up & Reconciling

In September 2019, the couple shocked their fanbase with the news that they were no longer together. Dreezy had posted a message on her Instagram Stories hinting that something was up with her relationship with Jacquees. “When I stop answering the phone, it’s a problem,” she said. She then took to Twitter later to announce her new single status. Along with a shrugging emoji, she simply tweeted: “Single.”

A month later, the R&B singer tweeted: “You can’t make me feel bad for decisions you made.” Dreezy wasted no time responding to the tweet. Believing he was speaking about her, she threatened to “expose” him on Twitter. She wrote: “When I air yo sh*t out on this app don’t say sh*t.” Nonetheless, it took the two a few months to reconcile, and they began dating again in early 2020.

October 2020: Jacquees & Dreezy Throw Online Jabs

In October, Dreezy and Jacquees not only broke up, but they brought their issues to social media. The pair exchanged many unsavory words on X (formerly Twitter). It all began when Jacquees tweeted: “JACQUEES single.” Dreezy subsequently shared her stance on the matter, writing: ”N*gga tryna clout chase now and KNOW I’m not wit all that sh*t at all. You’re blocked. I’m single. And I’m Logging off. Go play wit yo ex.”

Quoting her tweet, Jacquees responded in a now-deleted tweet with: “Go play wit ya self lol.” Almost as if she had been waiting for the perfect moment, Dreezy pulled up with some receipts. Mocking his tweet, she posted a screenshot of his missed phone and Facetime calls. She then tweeted: “When yu blocked so yu run to Twitter. Nobody gives af bro.”

While some fans were rallying behind Dreezy, some others tried to defend the self-proclaimed King of R&B. When one suggested that the singer’s account may have been hacked, Dreezy denied it, stating: “Ain’t nobody hack that n*gga he a hoe. I’m glad y’all get to see.” In the end, Dreezy concluded the entire matter with a tired tweet: “I tried it didn’t work. Moving on…”

June 2021: A Surprising Mexico Vacation & Dinner Date

In early June 2021, the on-again-off-again couple was spotted vacationing in Mexico. Many wondered if this was to rekindle their relationship. The vacation, however, turned sour when the two were involved in a fight. A man allegedly selling cocaine had physically assaulted Dreezy, and Jacquees defended her by going after the man. Dreezy soon took to Instagram to clear the air about the matter and tell her side of the story. 

As their vacation was almost ruined, the couple went out on another date to salvage their stay. They were spotted having a romantic dinner and enjoying each other’s company. As a result, this sparked new rumors that they were back together. However, the artists neither confirmed nor denied it.

February – April 2022:  Baecation Season

The couple continued to spend time with each other for holidays and on birthdays. In February 2022, the two were seen together on a vacation in Hawaii. A month later, they celebrated Dreezy’s 28th birthday with yet another vacation in Mexico. Jacquees celebrated his birthday the following month with a lavish party in Miami.

March – December 2023: 

By 2023, it was public knowledge that Dreezy and Jacquees had decided to keep their relationship going. In April, the “Cash Money” singer and Dreezy were spotted shopping for lingerie. The singer posted on Instagram that he had treated the rapper to a special date for her birthday that year. At this point, there were no reasons to doubt they were an item.

It all came to a startling stop in December 2023, however. Specifically, Jacquees shared a couple of photos and videos of himself and a woman vacationing in the Dominican Republic. While the pictures looked great, many fans couldn’t help but notice that the woman in question wasn’t Dreezy. Instead, it was Deiondra Sanders, daughter of Deion Sanders. Unsurprisingly, this kicked off rumors that Jacquees and Dreezy were no longer together, and he was now dating Deiondra. However, it wasn’t the end of his story with Dreezy.

February 2024: Shocking Revelations

A few days into February 2024, Deiondra Sanders tweeted about someone sending underwear to Jacquees’ house. “Obsessed is when you still sending underwear with your face on it to the crib,” she wrote. Evidently, the media believed this jab was aimed at Jacquees’ ex, Dreezy. As a matter of fact, even Dreezy took offense to the tweet. She wasted no time responding with a screenshot of a text chat with Jacquees. In the texts, Jacquees is seen asking to impregnate Dreezy, all while he was still with a pregnant Sanders. 

“Obsessed is y’all having a baby on the way but the n*gga begging to get me pregnant cus he barely fwu bird brain,” Dreezy tweeted.  Along with another screenshot of a text, she then stated: “Tf I turn yo n*gga own EVERYDAY for yu. And this the thanks I get around this mf?” However, with Dreezy seemingly ignoring Jacquees’ texts, perhaps things can finally end between them for good.  

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Young Thug & Jerrika Karlae: Relationship Timeline

The romantic saga between Young Thug and Jerrika Karlae has intrigued onlookers for years now. From the start of their relationship in the early 2010s, till their eventual split, they had the attention of the public. Now, a while after they parted ways, their post-breakup relationship continues to make waves. Things are also particularly interesting because Young Thug has been dating R&B singer Mariah The Scientist since 2021. Nonetheless, fans are now speculating that the rapper is still holding on to pieces of his time with Karlae.

A recent leak of his jail call footage revealed an old loved up photo of Young Thug and Karlae on the rapper’s wall. Following this discovery, fans have been in a frenzy over the photo, and coming up with several theories. While we can neither confirm nor deny any of those speculations, we can fill you in on the shared history between Young Thug and Jerrika Karlae. Here’s a timeline of their relationship.

Read More: Jerrika Karlae Decided To Rap And It’s Working: “U Ain’t Slime Enough” Rapper Talks Music, Relationships & More

2013: Young Thug And Jerrika Karlae Meet And Start Dating

It was sometime in 2013 that the two first crossed paths. Being that they were both already in the entertainment industry, it’s no surprise that they met in a studio. During a session at Gucci Mane’s studio, Karlae, accompanied by her mother, met Young Thug for the first time. Speaking to FADER in 2016, Karlae shared that she shrugged off Young Thug’s initial advances. “I was like, ‘you’re a rapper and I already know what that’s about,’” she said. 

While they didn’t hit things off on that first meeting, they soon became friends. Subsequently, as Young Thug began showing interest in Karlae and her businesses, she began to soften up toward him. Soon after, they officially started dating. “He’s not only so into himself, he’s so into me and he’s really seeing potential in me,” she told FADER. 

2015: The Couple Gets Engaged

Following almost two years of a blissful relationship, Young Thug asked Karlae to marry him. Up until then, their relationship had been drama-free, at least from the perspective of the public. The two seemed to be locked in and deeply in love, so when rumors of an engagement first surfaced, it didn’t surprise anyone. While the exact date of their engagement is unknown, reports claim it happened sometime in April 2015. On April 22, 2015, in an interview with AllHipHop, Young Thug confirmed that he was indeed engaged. 

Read More: Top 5 Collaborations On Young Thug’s “Slime Language”

2016: Head Over Heels In Love

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ATLANTA, GA – JANUARY 16: Jerrika Karlae and Young Thug attend “No Cap” Tuesday The Biggest Party Of The Year at Gold Room on January 16, 2018 in Atlanta, Georgia. (Photo by Prince Williams/Wireimage)

The pair did not immediately tie the knot after their engagement. However, in the months that followed, they seemed to be more in love than ever before. For example, in multiple now-deleted Instagram posts, they shared several PDA-filled photos. While there were likely some low points in their relationship over time, their dirty laundry never made it to the public.

2017: Young Thug And Jerrika Karlae Break Up

In late 2017, to the surprise of fans, Jerrika Karlae broke up with Young Thug. Up until then, their relationship had seemed to be almost perfect, so nobody saw a breakup coming. However, Karlae’s decision to end things was a result of Young Thug’s infidelity. On October 4, 2017, the YSL rapper shared on her X account, “I’m definitely back on the market tho.” 

Afterward, some drama ensued, with Thug quoting her in a now-deleted tweet of his own, writing, “What market? B*tch u goin d*e OnGod.” Subsequently, in November, the two had another bout of interactions on the platform. It seemed like Young Thug was remorseful, and wanted another chance with Karlae. However, soon after, the “Worth It” rapper claimed that his account was hacked, and deleted the pleading tweets. 

2018 – 2020: Reunion And Final Breakup

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ATLANTA, GA -JANUARY 29: Young Thug and Jerrika Karlae attend Migos “Culture” Album Release Party at Compound on January 29, 2017 in Atlanta, Georgia. (photo by Prince Williams/Wireimage)

Following a messy breakup in 2017, the pair seemingly began mending their relationship in 2018. While there was no official statement from either rapper, they shared pictures featuring each other on Instagram. Many months later, in December 2020, Jerrika Karlae went on a rant on X that many connected to Young Thug. On December 27, 2021, she posted, “single 2021,” a cryptic message that fans speculated was about her relationship with Thugger. Among other tweets, she also wrote, “Why misuse and abuse something or someone, why not leave them be! That’s some narcissistic sh*t. You behind the scenes painting pictures of me, like ima f**ked up individual…when you the devil”

2021 – Present: Moving On And Maintaining A Platonic Relationship 

Subsequently, Young Thug denied the allegations, claiming that he had been single for two years at the time. His claim made fans reassess, and conclude that maybe Karlae was, in fact, not speaking about Young Thug. Therefore, it remains unclear when exactly they ended things, or if they ever even officially got back together after the breakup in 2017. However, it’s clear that they have not been romantically involved since 2021 because Thugger began dating Mariah The Scientist that year.  

Since Young Thug was incarcerated, Karlae seems to have communicated with him a few times. During an interview on The Progress Report in June 2022, she revealed that she had spoken to Thugger. In addition, she shared, “He’s doing good. He’s in great spirits. I feel like this is just a moment for him to learn a lot of lessons.” While they are no longer a couple, the two seem to be in a good place platonically. However, the photo in Thugger’s leaked video has certainly raised some eyebrows. 

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Lil Scrappy & Bambi’s “Love & Hip Hop” Relationship Timeline

Reality television has a remarkable way of weaving together the extraordinary and the everyday. As a result, it pulls back the curtain on the lives of those who grace our screens. For example, there’s the on-again, off-again relationship between the rapper-turned-reality-TV star Lil Scrappy and Adiz “Bambi” Benson, documented extensively on Love & Hip Hop: Atlanta. Let’s embark on the chronological roller coaster of their relationship, from the early days to their eventual divorce.     

2013-2014: Crossing Paths

ATLANTA, GA – OCTOBER 05: Lil Scrappy (c), Lil Scrappy’s daughter Emani (L), and Bambi (r) attend the Breast Party Ever at Ventanas on October 5, 2013, in Atlanta, Georgia. (Photo by Johnny Nunez/WireImage)

Lil Scrappy and Bambi first crossed paths in 2013, on the second season of Love & Hip Hop: Atlanta. While Scrappy is known to be a major protagonist in the franchise, Bambi first appeared as a guest star and a potential love interest for the rapper, Benzino. However, things eventually took an interesting turn when Bambi returned in the third season as Lil Scrappy’s girlfriend. This also occurred just after Scrappy had broken off his nine-year relationship with his ex-fiancé, Erica Dixon.

2015: Bambi Supports Lil Scrappy Through It All

In 2015, Lil Scrappy got into a legal battle with Eric Dixon. The battle was over the custody of their daughter, Emani. He subsequently lost and was allegedly barred from being near his ex-wife due to threats of violence. Moreover, he was ordered to pay child support. Nonetheless, throughout the entire ordeal, Bambi showed support for her man and stuck by his side.

2016: A Brief Break Up

It came as a shock when Lil Scrappy and Bambi broke up in the fifth season of Love & Hip Hop: Atlanta. Bambi eventually went on to date rapper Alecia Dennis, and it seemed like the end of the couple’s relationship. However, Scrappy took a risk and proposed to Bambi in the season finale. She took him back and accepted the proposal, gaining the support of viewers and fans. 

2017: Lil Scrappy & Bambi Say “I Do!”

SANTA MONICA, CALIFORNIA – JUNE 15: Lil Scrappy (L) and Bambi attend the 2019 MTV Movie and TV Awards at Barker Hangar on June 15, 2019 in Santa Monica, California. (Photo by Emma McIntyre/Getty Images for MTV)

Bambi appeared on three episodes of the sixth season before she shockingly called off the engagement. Reportedly, her relationship with Lil Scrappy began to sour, leading her to quit the show. Unsurprisingly, this seemed to mark the end of their relationship, finally. Nonetheless, the two surprised the public once again by getting back together offscreen. By September 2017, the couple tied the knot in a private ceremony in Las Vegas. 

2018-2022: A Growing Family

The couple came back for three episodes in Season 7 of Love & Hip Hop: Atlanta. On the show, they announced that Bambi was pregnant with their first child. They returned the next season and chronicled the birth of their son Breland. Furthermore, their journey as parents evolved when they welcomed a daughter, Xylo, in 2020. 

Altogether, Lil Scrappy and Bambi continued to share parts of their lives on the popular reality show. By Season 10, they welcomed their third child, Cali. However, things became shaky when Scrappy’s mother, Momma Dee, found out that Bambi was planning to divorce the rapper. This led to a confrontation between the two women, which became a bone of contention on the show.

2023: Calling It Quits

After six years together, the couple called it quits and got divorced. In September 2023, Lil Scrappy hosted a massive party in Atlanta to celebrate his new single status. The rapper also took to his Instagram page to post a flier inviting everyone to his “Back Outside Divorce Party.” Since then, the former couple has stayed away from each other.  

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Austin McBroom & Catherine Paiz Relationship Timeline

Almost a decade ago, the YouTuber and entrepreneur Austin McBroom, and social media star Catherine Paiz’s love story caught the attention of millions. The power couple, known for their social media presence and family vlogs, shared their journey with the world at every level. From the early days of their romance to building a family together, they were very open and vocal about everything. Sadly, it seems their love story has come to an end, which evidently took the fans by surprise. Nonetheless, let’s catch up on how they went from lucky in love, to heading down the road to divorce. 

2015: Blooming Love

Austin McBroom and Catherine Paiz’s love story started in 2015 when both were carving their paths in the digital world. McBroom, a former NCAA basketball player, and Paiz, a model and aspiring actress, crossed paths at a dinner party. The chemistry between them was undeniable, but according to Austin in an interview with Power 106 in Los Angeles, it took Catherine a while to warm up to him. Catherine responded, saying: “I just wasn’t used to like, things happening so quick, and things being so real so quick.”

2016: A Joint Channel, & A Family

In May 2016, Austin and Cat welcomed their first child—Elle Lively McBroom. The birth of their daughter added a new dimension to their relationship and careers as YouTubers. Embracing the joys and challenges of parenthood, the couple launched their joint YouTube channel The ACE Family. The title of the channel was made by using the first initial of their names. 

The pair often documented their lives and adventures on the channel. Their entertaining vlogs, pranks, and challenges resonated with viewers, catapulting them to social media stardom. The channel not only showcased their love but also offered a glimpse into their growing family. As a result, their subscriber count skyrocketed, and they gained many followers on other social media platforms as well. 

2017-2018: Private Wedding, & Baby Number 2

In August 2017, Austin McBroom took the relationship to the next level with a grand proposal. After the pair had gone skydiving and landed safely, Austin proposed to Catherine and the latter said yes. The emotional moment was captured on video, and subsequently shared with millions of fans on their channel, solidifying their status as YouTube faves. 

Joyous, Catherine also shared the news with everyone on Twitter with a video of the ring and a caption reading: “WE’RE ENGAGED!!!!!!!! I’m at a loss for words. The man of my dreams just proposed in the most unbelievable way possible. I love you Austin.” Soon after, the couple got married in a very quiet and private ceremony that same year. Austin McBroom and Catherine Paiz also announced they were expecting their second child. In 2018, Alaïa Marie McBroom joined the family, bringing more love and joy into their lives. However, it wasn’t until 2020 that they admitted they had tied the knot. 

2019: Surfacing Scandals

In early 2019, Austin McBroom posted a Snapchat video depicting him purchasing a phallic-shaped lollipop for a girl believed to be a distant family member. The video was subsequently shared on Twitter by a fan, and it immediately sparked criticism. Specifically, many asserted that he was inappropriately sexualizing the child. As more people became aware of the matter, older, now-deleted tweets from Austin began resurfacing. The tweets featured comments he made about women, particularly Black and Asian women. 

Faced with the mounting criticism, Austin took to his YouTube channel to address the controversy with his mother. Despite the controversies, Catherine Paiz remained steadfastly supportive of her man. Eventually, as time passed, rumors soon began circulating that the couple were parting ways after she was spotted not wearing her ring. However, Paiz addressed the matter in a video and stated that she and Austin were not separating. “People may not fully grasp it at times… but he is my soulmate,” she said. “He is my other half, the person I am destined to spend my life with.”

In October, another scandal hit the ACE Family when beauty vlogger Cole Carrigan accused Austin McBroom of sexually assaulting her in a Miami hotel. She also claimed that he had tried to force himself on another woman but was unsuccessful. However, McBroom denied the accusations on Twitter, claiming that Cole was simply trying to extort him. He also stated that he would be taking legal action against the allegations.

2020: Austin McBroom & Catherine Paiz Welcome Baby Number 3

 
 
 
 
 
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A post shared by Catherine Paiz (@catherinepaiz)

In early January 2020, Catherine and Austin surprised fans with the announcement of their third child, the first boy in their growing family. Unlike their previous approach using a video, the couple chose to announce the news through photos on their individual Instagram pages. They also revealed the baby’s gender but refrained from providing any more commentary about the pregnancy on their YouTube channel at the time. The couple eventually welcomed their son, Steel McBroom, in June and also hinted that they were done having kids for now.

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LOS ANGELES, CALIFORNIA – JANUARY 02: Austin McBroom and Catherine Paiz attend a basketball game between the Los Angeles Lakers and the Oklahoma City Thunder at Staples Center on January 02, 2019 in Los Angeles, California. (Photo by Allen Berezovsky/Getty Images)

In April 2021, Catherine Paiz was sued by TBL Cosmetics for staging a coup. Paiz had reportedly entered into a contract with the company to serve as the face of their new premium skincare line. However, TBL alleged that she had engaged in a conspiracy with her family and friends to orchestrate a takeover of the line’s management. However, she denied all the allegations. 

Just months later, Austin was sued by the media company LiveXLive. The dispute arose following alleged complications during their celebrity boxing event. The icing on the cake eventually came in 2022, when the ACE Family lost their mansion. According to Insider, the family had received a notice of default from a debt-collection company, indicating a 90-day window to repay $8.7 million to a lender to whom they owed money. Unfortunately, the couple was unable to meet the obligation, resulting in the loss of their house, with ownership subsequently transferred to the beneficiary, 5 Arch Funding Corporation.

2024: The Road To Divorce

 
 
 
 
 
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A post shared by Austin McBroom (@austinmcbroom)

A lot of time went by, and the couple were toeing the line between public and private. However, earlier this year, Austin McBroom and Catherine Paiz shocked their large fan base when they announced that they would be closing the book on their marriage. On January 11, 2024, Austin took to his Instagram page to share the painful news. “We have mutually agreed to a divorce but will remain a team when it comes to our kids,” he wrote. “We created one of the greatest stories, almost a decade together, so many memories, so many accomplishments but every book comes to an end. And now we will be writing a new book as separate authors.”

The same day, Catherine also confirmed the news on her Instagram account. “We have mutually agreed to a divorce and will part amicably,” she wrote. “Our paths as a couple have shifted and have created challenges that are irreconcilable. This decision comes with a very heavy heart. As heartbreaking as this is, I also feel liberated.” 

Since that time, Austin has been sharing his single life on social media. He recently revealed that he was living in an RV on his neighbor’s property close to his former home. Fans are unsure if this is a real break up, but only time will tell.

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YG & Saweetie: Relationship Timeline

For several months, the relationship between Saweetie and YG has attracted public interest, notably exciting fans of the couple. Both prominent figures in the Hip Hop and staples on the West Coast, the pair captivated the hearts of many while they were together. However, recent development seems to prove that their romantic journey together may have come to an end. While fans were rooting for the couple, their relationship unfortunately lasted less than a year. Nevertheless, they seem to be ending things on a good note, so a win is a win. From its inception to its eventual end, here’s a timeline of YG and Saweetie’s relationship.

Read More: Most Surprising Celebrity Breakups Of 2023 (Thus Far)

March 2023: Whispers Of A Romance Between The Two

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LOS ANGELES, CALIFORNIA – MARCH 08: YG (Top), ASAP Ferg, Tyga, Mustard and Saweetie attend YG’s All Red Upscale Birthday Celebration at Melrose Place on March 08, 2023 in Los Angeles, California. (Photo by Jerritt Clark/Getty Images for 4Hunnid)

After being spotted together at an event in California on March 5, 2023, speculations started flying about the two being in a relationship. Subsequently, Saweetie’s appearance at YG’s all-red birthday party on March 8 slightly intensified the rumors. Many celebrities were in attendance, and the pair didn’t show any public displays of affection. As such, the rumors were largely unfounded. However, some fans insisted that the two were romantically involved. While it remains unclear if the two were already together in March, the speculating fans were soon proved right. 

April 2023: More Public Appearances Fueling Dating Rumors

 
 
 
 
 
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A post shared by the Jasmine BRAND (@thejasminebrand)

Following the first weekend of Coachella 2023, the Jasmine Brand reported that Saweetie and YG were seen getting cozy at the festival. If the dating rumors had been dying out, this news certainly brought them back to life. Subsequently, on April 18, the two were spotted again at Lala’s Wafflehouse in Indio, California. While Saweetie tried to mask her identity, fans always managed to recognize their fave. Altogether, their repeated sightings as a pair started making the rumors seem credible, and more people started believing them.

Read More: YG & Saweetie: Femcee Looks Uneasy As Her Ex Posts About Spinning The Block

May 2023: Relationship Confirmation, And A Mexican Baecation

By May 2023, the rumors had been going strong for about two months, and neither rapper confirmed nor denied them. However, towards the end of the month, the pair made a statement with their actions rather than words. Before May, they had never been caught being too affectionate, but that changed on May 30 when certain pictures surfaced. The photos shared revealed that the couple were on vacation in Cabo, Mexico. These photos also showed that they were finally being public with their displays of affection.

July – September 2023: The Couple’s First Public Date And Joint Tour Announcement

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MALIBU, CALIFORNIA – JULY 04: (L-R) YG, Alexander “A.E.” Edwards and Saweetie attend Red White & Bootsy at Nobu Malibu on July 04, 2023 in Malibu, California. (Photo by Vivien Killilea/Getty Images for The h.wood Group)

YG and Saweetie made their public debut as a couple in early July 2023. While the two stepped out to have dinner at Craig’s in WeHo, the paparazzi caught them. However, they didn’t mind at all, and walked hand-in-hand, as the footage shows. Soon after, they announced their upcoming Str8 to the Klub Tour with Tyga. It was set to kick off in September 2023, and finish in Las Vegas on November 21, 2023.

September – December 2023: YG And Saweetie Seemingly On The Rocks

Following their tour announcement in July, fans of the rap couple were excited to see their faves perform. However, in an unexpected turn of events, fans found out later in September that the tour had been canceled. In addition, it was soon discovered that the pair were no longer following each other on Instagram. As expected, this set fans into a speculating spree once again, with many suggesting that they had broken up. However, on December 28, they were spotted together at the Beverly Hills Hotel. This sighting eased the breakup rumors, but only slightly.

January 2024: YG And Saweetie Break Up

 
 
 
 
 
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On January 15, 2024, it was reported that YG and Saweetie had called it quits on their relationship. Moreover, YG was also spotted on his ex Kehlani’s comment section on Instagram. After his and Saweetie’s last sighting in December, this news came out of left field. However, it did not completely take fans by surprise as many had suspected that their romance was on shaky ground. Sources have told The Shade Room that the two decided to focus on their careers, and split amicably. However, YG seemingly shut down the rumors afterward when he shared two clips of himself and Saweetie getting cozy at a Beyonce concert.

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Keith Powers & Ryan Destiny Relationship Timeline

Among the myriad of captivating tales Hollywood provides daily, the relationship between Keith Powers and Ryan Destiny is a radiant saga. From the initial sparks of connection to the amazing love-filled photoshoots and the challenges that accompany stardom. Their journey is a fascinating exploration of two souls navigating the glitzy landscape of the entertainment industry while finding solace in each other’s company.

Ryan Destiny has continued to focus on her music and acting, while Powers is more prominent in the acting scene. While the two have said their goodbyes (at least romantically), many still hope their love will be revived. On the flip side, many believe they’re back together but are keeping their relationships private. Nonetheless, here are all the times they’ve kept us swooning since their first meet-up in 2015.

2015: Ryan Destiny & Keith Powers Meet  

Keith Powers and Ryan Destiny first crossed paths in 2015 at a Teen Vogue party. Although the initial attraction was undeniable, the real sparks ignited when they connected and began talking on Instagram. In an interview for the digital cover of WeTheUrban in 2019, Destiny spoke about how their relationship started. “For a minute, we tried to hide it for numerous reasons, but as human beings, sometimes you want to just shout to the world, ‘I love this person and I’m happy!’”

2018: A Glossy Red Carpet Debut

LOS ANGELES, CA – JUNE 24: Ryan Destiny (L) and Keith Powers attend the 2018 BET Awards at Microsoft Theater on June 24, 2018 in Los Angeles, California. (Photo by Johnny Nunez/VMN18/Getty Images for BET)

In a glamorous stride into the spotlight, Keith Powers and Ryan Destiny made their first joint appearance on the red carpet at the prestigious BET Awards in 2018. As cameras flashed and the world watched, the couple gave off such undeniable chemistry. As expected, the rumor mill was on autopilot as news of their attendance made headlines. While some fans believed the pair simply attended the event together as friends, others went into a frenzy. Nonetheless, it wasn’t until the following year that the pair officially confirmed their relationship. 

2019-2021: Relationship Confirmation & Becoming An “IT” Couple

In 2019, the couple made their relationship publicly official. Although they had embraced privacy over the years, the two decided to let the world in, albeit on the surface. They famously appeared together in magazine shoots and advertising campaigns, almost as a two-for-one celebrity bundle. The couple also dished out details of their love story on the digital cover of WeTheUrban in July. The fans weren’t complaining, however; they were eating up all the adorable moments. 

Ryan Destiny and Keith Powers continued to show off their power-couple status. If it wasn’t a sultry Calvin Klein campaign, it was sickly sweet social media posts. Fans ate each of these public displays with vigor, as evidenced by the extra-supportive comments. Evidently, the relationship had opened up a little more, and the couple seemed okay with it.   

January-August 2022: Break-Up & Staying Friends

After four years together, the two shocked the world when it was announced that they were going their separate ways. A trusted source had told PEOPLE that they were “taking time to focus on themselves and their emerging careers but are remaining close friends.” Following the report, Powers and Destiny continued to be friends as promised. However, the occasional sightings of the former couple in the aftermath of their public separation stirred up some speculation about a potential reconciliation among fans. In August 2022, for example, Destiny joined Powers and his family for his birthday weekend. Soon after pictures hit the web, the swirl of romance rumors reached new heights.

March, April, & June 2023: Numerous Public Outings

Since 2023, Keith Powers and Ryan Destiny have been regularly sighted together at ceremonies and award shows. In March, the two were seen enjoying each other’s company at the 2023 Essence Black Women in Hollywood Awards. The next month, the ex-lovers were spotted again at the Empire Polo Club in Indio, California, during the 2023 Coachella Festival. Alongside the other celebrities who attended, they seemed to be having fun at the Revolve Festival. To top it all off, Ryan Destiny accompanied Keith Powers as his date to the premiere of his film, The Perfect Find, during the 2023 Tribeca Film Festival.

August-December 2023: Partying Together

In August, just around Powers’ birthday, the two shared nearly identical selfies that hinted heavily that they were in the same location. The two attended the star-studded release party for Victoria Monet’s JAGUAR II album that same month. For Halloween, Destiny and Powers stepped out in matching hamburger and hot dog costumes for a party. In November, the fashionable duo attended the ”Imaginary Dinner,” hosted by the clothing brand Off-White in collaboration with FARFETCH. The two were spotted serving looks and sitting side-by-side at the table. Just a month after, Destiny joined Powers and his family to celebrate Christmas. The celebration was filled with games, dancing, and laughter.

January 2024: Ryan’s Birthday Bash

For Destiny’s 29th birthday in January, she threw a “Club RD” themed party in Los Angeles. The party was attended by many, including Keke Palmer, Normani, and, of course, Keith Powers. With every joint outing, fans are coming closer to believing that Destiny and Powers may have gotten back together in secret. However, they’re yet to confirm or deny these rumors. Regardless, they’ve made their friendship work and are evidently happy with where they stand. Although their romance is not confirmed, we can only wait for the two to be open about their relationship.

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Hugh Hefner & Crystal Harris: Relationship Timeline

Hugh Hefner, the iconic founder of Playboy, and Crystal Harris, a former Playboy Playmate, captivated the public with their high-profile and often scrutinized relationship. With Hefner 60 years older than Harris, many looked down on their relationship and believed Harris was only after Hefner’s fortune. Nevertheless, the two pushed forward with their love and were married until 2017, when Hefner sadly passed away.

Crystal Harris has since claimed that she’s ready to drop Hefner’s last name, and published a tell-all memoir in January 2024, titled, Only Say Good Things: Surviving Playboy And Finding Myself. It’s been met with mixed reviews, but Harris definitely dropped a few bombshells. This article traces the fascinating timeline of their journey through love, commitment, and the challenges they faced. 

Read More: Hugh Hefner: Rappers & Celebrities Pay Tribute

2008-2009: Initial Meetings And Moving Into The Playboy Mansion

SAN REMO, ITALY – FEBRUARY 20:Kristina Shannon, Karissa Shannon, Hugh Hefner and Crystal Harris attend the Playboy party at the Morgana restaurant on the fourth day of the 59th San Remo Song Festival on February 20, 2009 in San Remo, Italy. (Photo by Venturelli/WireImage)

Hugh Hefner and Crystal Harris met at Hugh’s 2008 Halloween party. Crystal, 22 years old at the time, was introduced to Hugh, and despite the incredible age difference, the two hit it off pretty quickly. Their connection quickly evidently deepened, and Harris became a regular presence in Hefner’s life. That same month, Harris was named “Co-Ed Of The Month” on Playboy.com.  By January 2009, Harris began dating Hefner and moved into the Playboy Mansion. There, she lived with Hugh and his other two girlfriends, the twin sisters Karissa and Kristina Shannon. In October of the same year, Harris made her debut on Girls Next Door. Two months later, she was crowned “Playmate Of The Month.”

2010: Hugh Proposes To Crystal Harris 

Crystal Harris
(GERMANY OUT) Hugh Hefner and Crystal Harris at the TCM Classic Film Festival in Hollywood (Photo by Manfred Segerer/ullstein bild via Getty Images)

On Christmas Eve 2010, Hefner proposed to Crystal Harris with a 3.39-carat engagement ring and Harris said yes. Evidently, despite Hugh’s two previous marriages, he was still willing to give love a chance. Soon after, the couple announced their engagement to the public. Hefner posted on Twitter, stating: “When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory.” The news shocked many and the announcement of their engagement raised many eyebrows, especially considering their age gap. While Hefner was known for his many girlfriends, marriage was rarely a step for the casanova. As a result, many believed the 22-year-old was solely attracted to Hefner for his extensive wealth associated with Playboy.

June 2011: Crystal Harris Calls Off The Wedding 

Even though Hefner was ready to spend the rest of his life with Harris, it seemed she did not feel the same way. Mere days before they were scheduled to exchange vows, Crystal decided to cancel the wedding. She went on to speak on Entertainment Tonight a few days later, explaining her decision. “I wasn’t the only woman in Hef’s life,” she said. “I didn’t feel comfortable in my heart knowing that and getting married to him because a marriage is between two people.”

Read More: Hugh Hefner’s Wife Crystal Harris Was By His Side Until The End

July 2011: Throwing Shade

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HOLLYWOOD – APRIL 26: Hugh Hefner (L) and Crystal Harris arrive at the “Iron Man 2” World Premiere at El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Jeff Vespa/WireImage)

Just a month after the wedding was canceled, Crystal went on Sirius XM’s Howard Stern Show. There, she threw shade at her former fiancé and their sex life. “The sex lasted like two seconds. Then I was just over it,” she said. She ended by claiming she “walked away” and was “not turned on by Hef.” The information did not shock many, especially considering Hefner’s age at the time. Nonetheless, Hefner took the matter to heart and fired back in a now-deleted tweet. “For the record, I have sex on a weekly basis. And I did throughout my two-and-a-half years with Crystal.” The pair were ultimately believed to be over, and for months, did not exchange words publicly. 

2012: Hugh Hefner And Crystal Harris Reconcile And Exchange Vows

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BEVERLY HILLS, CA – AUGUST 07: Playboy founder Hugh Hefner (L) and TV personality Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises, Inc.’s celebration of the return of Playboy headquarters to Beverly Hills on August 7, 2012 in Beverly Hills, California. (Photo by David Livingston/Getty Images)

Surprising many, Hefner and Harris reconciled in mid-2012. Moreover, they announced their renewed engagement. Harris tweeted that she was “his #1 girl again,” and that they were both happy. Hefner went more in-depth about how they reconciled in his own tweet, however. “It’s Mary O’Conner that brought Crystal Harris back. Crystal was miserable and said so. Mary told Crystal to write and tell me, which she did,” he wrote.

Hugh Hefner and Crystal Harris finally tied the knot on December 31, 2012, in an intimate ceremony at the Playboy Mansion. The wedding was attended by Harris’ family and Hefner’s four children. Unsurprisingly, it was reported that Crystal was required to sign an “iron-clad” pre-nuptial agreement. This was in an effort to safeguard Hefner’s massive fortune.

2013: Enjoying Married Life

Crystal Harris
HOLMBY HILLS, CA – MAY 09: (L-R) Crystal Harris, 2013 Playmate of the Year Raquel Pomplun and Hugh Hefner attend Playboy’s 2013 Playmate of the Year luncheon honoring Raquel Pomplun at The Playboy Mansion on May 9, 2013 in Holmby Hills, California. (Photo by Christopher Polk/Getty Images for Playboy)

Throughout 2013, Hugh Hefner and Crystal Harris were photographed attending various events together, portraying a united front. The couple’s lifestyle, which included a bustling social calendar and the glamorous world of Playboy, was closely followed by the media. Despite her previous confidence, Harris was elusive when discussing their intimate life post-marriage. Nonetheless, they remained heavily on the paparazzi’s radar that year. As time went on, media coverage on their lives began to dwindle.

December 2014: A Welcoming Christmas Tour

To share in the holiday spirit, Harris provided fans with an exclusive glimpse into the holiday festivities at the Playboy Mansion. Posting the tour on YouTube, Harris stated: “It’s the best time of year not just ’cause of gifts and stuff, but because of my friends and because of [my Christmas tree] and because it’s just such a cozy holiday. I love it. Christmas is my favorite holiday!”

September 2017: Hugh Hefner’s Passing

The legendary Hugh Hefner passed away on September 27, 2017, at the age of 91. Crystal Harris mourned the loss of her husband, expressing her grief and gratitude for the time they had together. Speaking to PEOPLE after the funeral, she said: “I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day.”

2018-2023: Crystal Harris’ New Life After Hugh Hefner

Crystal Harris, now widowed, continued her life outside of the Playboy Mansion. Unlike what many people assumed, Hefner did not leave a large chunk of his fortune for Harris. She also eventually moved out of the Playboy Mansion to Hawaii. Harris soon ventured into different pursuits, and her post-Hefner life became a subject of interest for those who had followed their relationship.

2024: Starting From The Beginning

Harris’ tell-all memoir was published in January 2024. It detailed many events that happened in the Playboy Mansion, and away from the public gaze. Harris also spoke about how she was forced to conform to Hefner’s views and wants, both physically and emotionally. In an interview with CBS Mornings, Harris admitted to never loving Hefner. She said: “I don’t think it was love. I did care for him. He was getting older and I know he wanted to protect his image… I felt sorry for him in a way and I felt that he really needed me.” As aforementioned, the memoir has polarized the public.

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