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Kristin Cavallari Recounts Diddy Asking Her Out: ‘Red F–king Flag’

By Michael Feb 7, 2024

Kristin Cavallari said she “dodged a f–king bullet” by turning down Sean “Diddy” Combs.

“One Valentine’s Day, I was 22, I believe, we had a mutual friend, he got my number, whatever. He sent me the biggest bouquet of flowers I’ve ever seen,” Cavallari, 37, recalled on the Tuesday, February 6, episode of her “Let’s Be Honest” podcast. “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 s–t.’ I mean, it was like multiple people bringing s–t into my house. It was like s–t you see in a movie.”

Cavallari said Diddy, 54, had “a TV crush” on her at the time, but she eventually turned down his offer.

Cavallari’s cohost Justin Anderson acknowledged Diddy is now in “hot water” amid multiple sexual assault allegations. His ex-girlfriend Casandra “Cassie” Ventura, whom he dated on and off from 2007 to 2018, filed a lawsuit against Diddy in October 2023. He denied wrongdoing and settled the suit. Since then, several other women have come forward with new or past accusations, including Danity Kane singer Aubrey O’Day and Kimora Lee Simmons.

A Complete Guide to Kristin Cavallari’s Dating History

When Cavallari’s cohost asked whether she was tempted to go out with Diddy, she admitted the grand gestures were tempting.

Kristin Cavallari Recounts Diddy Asking Her Out on Valentine s Day
Diddy performs onstage during the 2023 MTV Video Music Awards. Noam Galai/Getty Images for MTV

“I mean, there’s obviously a part where you’re like, ‘Whoa, this guy is spoiling the s–t out of me.’ Like that’s so sweet, and I’ve never met this guy. Imagine if I was in a relationship with him, like how sweet it would be,” she said. “At the time, because I was 21. Now, as an adult, I’m like, ‘Red f–king flag!’ And clearly. I mean, that’s some love-bombing kind of s–t.”

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Although Cavallari and Diddy “talked a little bit,” she simply wasn’t interested in the rapper romantically.

“And I’ve got a lot of stories like that, you guys, where I could never just go on a date with someone because it was so-and-so,” she said. “Like, I literally always have had to be attracted to you.”

By Michael

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