Rosie O’Donnell throws some shade at Diddy and predicts he’s headed for jail? TLC was in stitches over it, and Chilli was laughing the loudest! I’ve got a joke for you—check this out! This year’s Grammy nominations are wild. Lauryn Hill has four nominations, TLC has eight, and Diddy’s got anywhere from five to ten. It’s almost like he’s trying to get a ticket to jail, right?
I was going to say, “Look, look, look…” but I don’t want to come off as mean. I mean, Diddy’s a nice guy and he can actually sing.
Oops, I guess that joke didn’t age well! But it really makes me curious—what did the members of TLC see back when Usher was working with Diddy? Especially Chilli, who was dating Usher at the time. I wonder what she really saw behind the scenes. The streets are buzzing with stories about what Chilli might have witnessed. Just imagine their late-night pillow talk. Did she know about Stevie J?
Now, that’s a sensitive topic! I had a lot of feelings when Usher appeared on Shay’s show and talked about how much Diddy taught him about the music business. You know what I mean?
You know, it’s pretty well-known among people who were around back then that Puff and Usher had some sort of situation that even led to Usher ending up in the hospital. Before we get into the details, I just want to say I’m reporting on what’s already out there—so please don’t come at me for what I’m about to share. When it comes to Usher, there hasn’t been any solid evidence tying him to all this Diddy drama—just a lot of speculation floating around. But people are saying we should probably take a closer look at Chilli for some answers, and I’ll explain why.
Usher and Chilli first met when Usher signed to LaFace Records, the same label Chilli was with. As we know, Usher got sent to Diddy for mentoring, and at just 14, he moved to New York to live with him. That meant he had to go through what was famously known as the “Puffy Flavor Camp.” Eventually, Usher started dating Chilli, and she even appeared in some of his music videos, like “You Remind Me” and “You Got It Bad.”
This raises an interesting question: could Chilli have seen some of the things Usher said he experienced while living with Diddy? Since they started dating after that time, it’s possible Usher shared some of those stories with her.
Usher himself mentioned, “I moved to New York City and lived with Sean Puffy Combs for a year,” which sounds pretty wild. It was actually La Reid’s idea—he suggested sending Usher over to “Puffy Flavor Camp.” Just think about what that must have been like—Puff’s place in the ’90s was probably filled with people and nonstop activity.
You know, not really, but it was definitely interesting. I got to see a lot of things.
But what were you really noticing at 13? I went there to check out the lifestyle, and I did—though I can’t say I really understood everything I was seeing. It was pretty wild!
After three years together, Chilli and Usher decided to split up, and that’s where the real gossip starts. Back in 2004, Chilli hinted that cheating was a big factor in their breakup. She mentioned on the “Atlanta Q100” show that Usher committed the ultimate betrayal, saying she would never take him back.
“He did the ultimate no-no. You just don’t do that, and he did, so it’s over; he ruined it. He really did.”
Chilli went on to say that if someone cheats once, there’s no reason to stick around to see if it happens again, basically saying Usher cheated on her. In an episode of V1’s “Behind the Music,” she shared that she had heard rumors about infidelity, which she confronted Usher about, and he actually admitted it.
“He admitted it. I felt so foolish. It seemed like everyone knew something I didn’t, and I was just now finding out.”
Fast forward to 2013, Chilli was still talking about how hurt she felt. She told “US Weekly,” “In any relationship, including mine with Usher, when it was time to make a change, I had to do it, no matter how much it hurt. Sometimes you’re meant to be with someone for a reason, but not always for a lifetime. Even if you wish it were different, it just doesn’t always work out that way. I’ll always love him because he was my first real love, but we’re good now. No hard feelings; it’s all good.”
In a recent interview, Chilli claimed that Usher never cheated on her, which really contradicts some of her earlier statements. At one point, it was suggested that Usher’s infidelity led to their breakup, but now there are whispers that Diddy might have been involved. Some people are even saying that one reason Chilli left Usher was that he allegedly gave her an STD—one he supposedly got from Diddy. Just to be clear, I’m not making this up; I’m just sharing what people are saying.
We’ve also heard reports about a tape featuring Usher and Diddy, along with claims that Usher’s mom confronted Diddy after learning about their rumored intimacy and the STD situation.
Jean Deal, who has spent a lot of time around both Usher and Diddy, confirmed that there was a serious incident that landed Usher in the hospital. Jean believes Usher shouldn’t have praised Diddy during his interview on Club Shay because they both know what really happened between them. And if you’re wondering why Jean waited to speak up about what he saw, well, I can’t say. That’s a question for Usher to answer when he’s ready to share his side of the story.
How can you say you’re just going to give a man a pass? Seriously? There’s something interesting going on with Diddy and Usher that I heard about. Apparently, while Kim Porter was sifting through some security footage from Uptown Records—because she had a gut feeling Diddy was being shady—she stumbled upon some unexpected footage of Diddy hanging out with Andre Harrell.
Kim definitely didn’t expect to see Diddy and Andre when she was going through those recordings, but she found it and decided to keep it. And get this—rumor has it that she didn’t just find footage of Diddy and Andre; she also had videos of Diddy allegedly taking advantage of Usher.
Some people are suggesting that Usher’s time with Diddy might have led him to develop some serious issues, which could explain why he was cheating on Chilli left and right. There are studies that say when someone experiences sexual assault at a young age, they might later become hypersexual. Many believe this could be what happened with Usher while he was with Chilli.
It seems like Chilli might be the one that got away, and Usher could still be hoping for another chance since they were in touch until a few years back. That might also explain why he can’t stop talking about her. Just recently, in February 2024, Usher reminisced about his relationship with Chilli, telling People magazine, “Honestly, I was her number one fan, and she was my superstar. When I was eight, I had her poster on my wall, and I thought, ‘Wow, that girl is so beautiful; one day, I’m going to meet her.’”
He hinted that distance might have played a role in their breakup, saying, “I was a young guy, and she had some pretty specific rules that didn’t really work for me. We were missing each other. I wanted a different kind of relationship where she could be there with me, but she just couldn’t. She didn’t really believe that I loved her as much as I did.”
Usher also mentioned that he proposed to Chilli right before they split, sharing, “I wanted to marry her; I asked her to marry me, but she said no. That hurt a lot. It took me years to get over it. I had to swallow my pride and all that. If it hadn’t been for her strong beliefs, I don’t know if I would’ve been able to move on.”
Wow, that’s pretty heavy. But if Usher didn’t cheat, what does that mean for Chilli?
You have to understand this whole dynamic. If Diddy, Usher, and Chilli have any sort of connection, it raises questions about how Diddy feels about Usher reconnecting with Chilli—if they’re even friends now.
There are rumors that Chilli left Usher for Diddy, but that’s just gossip, right? It’s kind of mind-blowing to think that Chilli’s past with Usher might somehow link back to Diddy’s actions. But is there any truth to that? I guess we’ll have to wait and see.
What do you all think? Could this lead to a future collaboration? Do you think Chilli would be open to rekindling things with Usher after everything that’s gone down?
