Kristin Cavallari on Turning Down Diddy: ‘I Dodged a Bullet’

In her latest podcast episode, the reality star revealed she was doggedly pursued by Diddy—with chocolate, tequila, and a teddy bear—in her early 20s.

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Kristin Cavallari on Turning Down Diddy: ‘I Dodged a Bullet’
Photo:Vahan Stepanyan, Tinseltown (Shutterstock)

Valentine’s Day is just around the corner, meaning we’re all probably feeling a little nostalgic about how we’ve spent Valentine’s Days of years past—from the good to the bad to the bullets gone blessedly dodged. Such is the case for Kristin Cavallari, who just shared a particularly memorable Valentine’s Day of her own.

“Wait, why can’t you share the story about…the massive Valentine’s Day? Can’t you just say his name?” Justin Anderson, Cavallari’s best friend, asked the reality star and entrepreneur on this week’s episode of Let’s Be Honest With Kristin Cavallari.

“He’s not a good look right now. Do you know all the shit going on?” Cavallari replied. “I can say it, it’s not a big deal,” Anderson volunteered. “P. Diddy. Puff Daddy….I didn’t really look into it but yeah, he’s in hot water right now.”

Of course, they’re referring to the rapper’s myriad lawsuits—all of which accuse him of deeply disturbing sexual violence. In November 2023, Sean “Diddy” Combs settled one of those suits with his ex-partner, Casandra “Cassie” Ventura, who alleged that he’d physically and sexually abused her throughout their relationship. Combs has denied all of the allegations.

“Well, I dodged a fucking bullet there!” Cavallari justifiably boasted before revealing that the rapper pursued her pretty aggressively for a time in 2009 when she was around 22 and he was about 40.

“OK, so one Valentine’s Day, I was 22, I believe,” Cavallari recalled. “We had a mutual friend, he got my number, whatever. He sent me the biggest bouquet of flowers I’ve ever seen. The biggest box of chocolates I’ve ever seen. A huge teddy bear. All of his tequila, because he had a tequila brand at the time, I don’t know if he still does. And I mean, it was like, holy shit. I mean, it was like multiple people bringing shit into my house. It was like shit you see in a movie.”

Ah, yes. All the shit you see in movies or read about in psych journals about love bombing. Sidenote: I like flowers. And I especially enjoy chocolate and alcohol. But I’ve never gotten the whole stuffed animal thing—especially as a gift to a grown woman. If she can drive a car, vote, and legally purchase alcohol, she can get her own damn teddy bear, no?

“And then he told me he had a TV crush on me and he wanted to take me out,” Cavallari continued. A “TV crush” huh? So, Combs was tuning into Laguna Beach and The Hills…interesting.

In the end, Cavallari said, she turned him down though it took more than a few times as he just “kept asking.” Apparently, she has multiple stories about so-and-so asking her out, only for her to deny them because she wasn’t all that attracted to them. Cavallari and Anderson then went on to discuss how dating certain people in Hollywood can make (or break) someone’s career.

“That’s the thing, is people will do anything to be famous,” she said. “I mean, there are fake relationships all the time…it’d be like if I actually went down the P. Diddy road, because it was going to make me more famous. It’s like, you do it because you know in the back of your mind, it’s good for your career.”

Fortunately, it seems like Cavallari’s managed just fine on her own.

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