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Caresha barely blinks. She’s an endearing presence with a steady, somehow both warm and unnerving gaze. It’s like she wants it to be known that she’s here. That she’s listening. But that steadiness seems to be a tool to mask her nerves. It’s been almost a year since she launched Caresha Please and she’s reflecting on its success, and the energy she brings. “I be nervous as fuck,” she whispers in earnest about interviewing her guests. “I’m a shy speaker, I got a strong accent. I talk different. So when I do it, I be so nervous… But now I’m getting more comfortable and having fun with it.” Caresha, the host, officially launched Caresha Please in 2022 to much discourse and buzz, as the lord intended. We get into it, and it’s impossible to talk about the show she now famously fronts without speaking of Diddy. The rap mogul and businessman, who recently added Love to his list of tags, is part owner of DeLeón tequila (sponsor of the show), and owner of Revolt network, home of both Caresha’s podcast and Respectfully Justin, a podcast with Diddy’s son Justin Dior Combs and IG meme curator and “Demon Time” founder Justin Laboy—the self-proclaimed “toxic duo” that hasn’t released new episodes since August of 2021. But during her and JT’s appearance on the latter, the idea of dipping into media was planted.

“Diddy had came and then after the show, [he] was like, ‘I like the way you was answering them questions,’ and that hit me off guard. I was like, ‘Huh?’ [and] he was like, ‘You got such a great strong personality; I want to link up with you or whatever.’ So I had ended up linking up with him at Miami at his house, and he was like, ‘You ever thought about doing a podcast?’ And I was like, ‘No,’” she says with a straight face. “[But] he was like, ‘I think you would do good. I think you’d be a great host.’” Although she was hesitant at first, Caresha’s team echoed the sentiment, encouraged the venture, and eventually convinced her to take the leap.

“I don’t feel like you should mix friendships and romantic relationships into business because it never works out. It’s too personal.”

So, naturally, for the inaugural episode of the podcast, which they ultimately launched in June of 2022, the two sat face-to-face as Caresha, the lover, gave viewers a taste of the deliciously daring energy she’d subsequently bring to the ongoing series. Similar to shows like Drink Champs or the newly launched The Wine Down With Mary J. Blige—on which Caresha and Taraji P. Henson served as the R&B legend’s first guests—alcohol acts as a guest of honor on Caresha Please. She recalls being the most drunk when interviewing Diddy, G Herbo and Latto, in that order. She was so drunk on the first taping with Diddy that it required a whole reshoot, resulting in what we ended up feasting our eyes on. She laughs at the memory now, saying, “I’ma tell you the truth… Say today is Sunday; we had did Caresha Please on Saturday. I got so drunk that we had to do it again on Sunday… I had to scratch it.” 

Among the many spotlights from that episode was the question of how they individually handle romantic partnerships; at the time, Caresha said, “We ain’t done until I say we done.” Nine months later, when I ask if they’re done, she says, “I will say this. I will say that I am single. That’s my friend. He gon’ always be my friend… we were friends first. But yeah.” Period.

An hour or so after our chat, she went on Twitter to reflectively punctuate that thought and expand on her learnings from the entanglement, writing, “I’m not sharing my next [ni***a]!”

The two spawned dating rumors in 2021 and developed a kindred friendship since, fueled by ambition and love. They never publicly defined their romantic relationship, and media pundit DJ Akademiks commented on that decision, unprompted. In December, when Diddy formally announced the birth of his family’s latest addition (he and Dana Tran’s daughter Love Sean Combs), the podcaster referredto Caresha as a “side bitch.” Dear friends like rapper JT and makeup artist turned rapper Saucy Santana—who she credits as the reason the show bears its name—swiftly came to her defense, writing “With them, it’s a good situation…. They’re a power couple.” 

Reflectively, when asked about conjoining the intimate and professional, Caresha advises against it: “I don’t feel like you should mix friendships and romantic relationships into business because it never works out. It’s too personal.” 

She speaks on that particular exchange with DJ Akademiks in December, as well as the influence that media personalities like him hold, and puts it plainly: “They some bitch ass [n****s].”

The controversial male hip-hop media personality is prevalent in the space Caresha stands in. They’re the norm rather than the exception, and some of its most influential figures have built large followings because of their dangerous rhetoric and general affectation of superiority over women rather than in spite of it. Over the last few years, in tandem with their rise, several of them—including Joe Budden, DJ Akademiks, Adam22 and others—have been accused of alleged sexual assault or harassment and have had both their content and personal integrities questioned by members of the media who they now share prime real estate with. In the days following unfavorable accusations, their close collaborators, partners and follower counts tend to fall off. But why is it that folks who promote misogyny, hate, and extremism are allowed to take up so much space and remain?

For many, when they want to start a fire, call attention to themselves online and via press, they ensure chaos and clicks with thoughts they likely wouldn’t utter vis-à-vis. In 2022, Akademiks and DJ Vlad bonded over Doja Cat’s dislike for them. That same year, DJ Akademiks pulled a targeted fake news campaign undermining Megan Thee Stallion’s credibility during The People v. Daystar Peterson, the trial that ended with Tory Lanez being found guilty of shooting her, only to admit Lanez’s wrongdoing after the verdict was announced. Most recently, this year, Latto confronted Adam22 after he made fun of her for interacting with someone who didn’t know who she was. “[You] wouldn’t try a male rapper like this,” she wrote. 

“I really think they should keep that energy for men,” Caresha suggests. “And I really think that they should stop speaking on women because why the fuck you care? Whatever I have going on in my dating life, why is it important for you to speak on a female on your pod or whatever it is? You got so much shit to talk about.”

Caresha would know. She’s having fun with it, but she’s also using her platform to address serious real-life subjects, including mental health. In conversation with Chicago rapper G Herbo, she got him to discuss everything from how he deals with PTSD after the death of his brother to his past cheating tendencies, and, in turn, he got her to answer a couple of questions herself—including whether she likes gangsters or gentlemen and if she knew about Diddy’s baby before October—a rare mutually symbiotic moment that gave the host a taste of her own medicine. Her stretch of range is impressive. Caresha’s interviewing skills are perhaps best displayed on this season’s second episode, which led pseudo-psychologist rapper Kevin Gates—who’s usually stoic and clear in his delivery—to go from stepping over his own words to gleefully uttering, “This is my favorite show.” Coincidentally, it was also Caeresha’s favorite episode thus far. “[He]had my mouth to the floor the whole interview. I was like, ‘Are you for real?’”

Not everyone is ready for the smoke though, and Caresha’s aware of that. But she doesn’t seem to have trouble filling the roster. “They don’t even be coming to the interview thinking that they will open up or touch on certain topics… I know some people be like, ‘I don’t want to come on there. She’s too messy or da, da, da,’” she laughs. “But people really come on there and have a good time… that’s the most fulfilling part—people coming on the show, being open and really enjoying themself and being vulnerable.”

Her expertise and appeal lie not in academic study or the conflict-ensuing approach of some of her peers but in genuine interest in the unseen lives of her friends and equals. As is the case with traditional journalism and any medium that involves a mic, the wall of acceptability in what is asked to a stranger or acquaintance is torn, and she’s left pulling from the rawest of questions in her hat. “Do you like making love or f**king?,” she asks Diddy, “So many people speak [poorly] about having a BBL… how would you respond to that?” she asks Latto, or “Is it hard to not cheat while you’re on the road?” she asks G Herbo. It feels as if the viewer is peeking into a private chat between close friends—because, most of the time, they are. Unguarded, the familiarity of kinship allows for unhinged conversations.

“I know some people be like, ‘I don’t want to come on there. She’s too messy or da, da, da.’ But people really come on there and have a good time.”

She does all this while pushing DeLeón and her own products like the Resha Roulette, a card game that makes an appearance on each episode, which typically sells out, reminding us that the bag is the goal. With Caresha Please, Caresha positions herself as a savvy businesswoman, too, and wiith an average of 3.2 million YouTube views, she surpasses the viewership of her loudest peers.

Thus far, the show has featured three men and five women, and when I appear startled at the fact that Denzel Washington is one of her dream guests, she gets to the idea that guys make for great couch heaters and wild spitters. “I feel like guys are very interesting. I like to see things through their eyes. They think differently than women. So, I just really be wanting to know what’s going on in their head.” A relatable sentiment.

She has two more episodes to go to wrap up Caresha Please’s first season and doesn’t know who’s slated yet but has an idea of who she’d like to interview next. Future dream guests also include Lori Harvey and Beyoncé (to talk “girl things”). And as the show continues to solidify its identity and reach, artists are tapping her and her team to be on the show, too. Most recently? SZA. The two have yet to meet, but the thought of the union excites her. “She was supposed to come on the show and I was like, ‘Really?’” she beams. “I love that ‘cause I feel like SZA is very quiet.”

At 28, Yung Miami, which she describes as her more “savage alter ego,” has laid down many wigs (two in the span of our time together–one pin straight that wisped by her hip and the other right above the shoulder, giving her the air of an anchor); the mother of two has had a rather unconventional and specially configured path to stardom that makes her feel both new and seasoned in the space depending on the setting. Music is what got her in all of the rooms. A mere four years ago, Caresha, the rapper, and JT were signed to Quality Control. Their story thus far—unraveled and presented in docuseries form by both MGX Creative and Mass Appeal—is one of triumph. The duo became the first two women on the label, also home to Lil Yachty, Lil Baby and Quavo; they had little experience and two songs under their name, but QC’s co-founders, Coach K and P, saw into their future. City Girls released their first studio album, Girl Code, in April 2018 and had an affirming co-sign when Drake tapped them to be part of his song “In My Feelings” that July. The song was released with much of their original contributions chopped with the exception of their interlude, Drake name-checking them in the hook, and Yung Miami’s appearance in the video. It came out on the same day JT turned herself in for credit card fraud in June 2018. She would go on to serve over a year of her sentence, and her counterpart was tasked with keeping the entity alive and relevant, while pregnant. “F*ck that Netflix and chill, what’s your net worth?” she spits on the track.

Yung Miami has taken a backseat to Caresha over the last few months with the growth of Caresha Please, but she’s still top of mind for the multi-hyphenate. She’s well aware of the inklings and commentary surrounding she and JT’s partnership. Duos are few and far between these days, and women duos are particularly so, with Salt-N-Pepa paving the way for them to have a seat at the table, a mission many opt to fill alone. Recently, JT’s sentiments on things coming between them, shared in conversation with Angie Martinez on her IRL podcast, sparked skepticism on the future of the duo overall. But, Caresha is cocksure.

“I don’t think that we would ever split up. Sometimes we go through shit. Like sometimes, we not speaking months, weeks… I can think, ‘Oh yeah, I could do it without her.’ She could think, ‘Oh yeah, she could do it without me.’ But it’s like we’re better as a group. I feel like two is better than one,” Caresha says. (The two just performed at Dreamville Fest and are on the lineups for the Roots Picnic and Broccoli City Festival.) “I feel like the world can push ‘cause I read a lot of tweets and everybody like, “You want JT to go solo, solo, solo, solo, solo.” And when groups separate, it’s really, like, when you come out as a group, you better as a group… Sometimes we don’t feel like doing it. But I don’t see us splitting up. That’s not a worry, and I don’t see it. I don’t feel it. Or at least I just feel like I don’t see it no time soon.”

Despite being willfully and joyously tethered and in pursuit of further growth with the City Girls, Caresha is building a solo name and identity for herself on her own terms. In the music studio, she recently exhibited her pen’s chops with a quick dip into Lola Brooke’s fun forewarning track “Don’t Play With It;” her pithy verse proves she can hold her own. In the podcast studio, she further leans into that unabashed, raw persona by drawing inspiration from no one… except maybe Oprah. 

In an off-the-cuff tweet from September 2022, Caresha called herself “The next ((((BLACK)))) OPRAH!!” She doubles down and explains, saying: “I feel like you have to put ‘Black’ in front of everything. Let people know it’s Black as f**k…I’m the next f**king Black Oprah. I’m the next Black young bitch that come from where Oprah came from. I’m going to be where she’s at. You get what I’m trying to say? That’s what I meant… Some people got it and some people didn’t. I wasn’t trying to take away from Oprah being Black. Oprah is Black.” 

Aside from the obvious, Oprah was, too, a meteor-like arrival. Like the dichotomy of the persona and being, Caresha brings the smoke but is a breath of fresh air. She didn’t enter this space with the intention of being a disruptor but has already become one. While women continue to intentionally take up space in the hip-hop genre and its offshoots, and toxic men ideally déclassé as a consequence of their own actions, Caresha isn’t worried about the competition––because she doesn’t believe she has any.

“I’m never worried about what no man got going on. I don’t give a fuck,” she says. “That’s for your wife to do. Or your bitch.”