I need Kristin Cavallari to write a 500-page novel about her dating life at this point. On the first episode of her E! reality show, Honestly Cavallari: The Headline Tour, the former Laguna Beach star casually dropped a bombshell about a steamy evening she once shared with (drumroll, please) Glen Powell. As in the 2024 White Boy of the Year Glen Powell. As in the Hit Man, Anyone But You, etc. Glen Powell. Apparently, the millennial blondes once went on a date and had a “really fun night” together that involved… “dry humping.” (Leave it to Kristin to really paint a vivid picture.) I’d pay to see Glen’s publicist’s reaction to that one.

This latest revelation has fans raising eyebrows and taking notes because girlie’s roster is low-key one of the most intriguing in Hollywood. From fellow reality stars to country singers to GP himself, she’s really dated ~across genres~. Some of us are particularly invested in her journey because we have no love lives of our own. For those of you who are also living vicariously through this diva, here’s everything to know about Kristin Cavallari’s Glen Powell hookup, plus her wild roster.

Kristin Cavallari And Glen Powell Hookup: Details

Image Credit: Getty

Image Credit: Getty

Kristin’s E! series, Honestly Cavallari: The Headline Tour, follows her as she takes her podcast, Be Honest, on the road. The multi-city tour promises plenty of juicy conversations with her famous friends, exes, and fellow reality stars — and the drama kicks off immediately in episode one, which premiered on June 4.

During the debut episode, Kristin’s bestie, Justin Anderson, brought up the Glen Powell rendezvous. He revealed that she “recently went on a date” with the actor, adding, “She’s gonna be so mad at me actually.” According to Kristin, Glen “literally ran into [her]” while she was out with Justin one time. Justin cheekily reminded her, “You guys had a really fun night together.” Teeaaa.

Kristin emphasized that she “never fucked” Glen, but she admitted that it wasn’t exactly PG either. When Justin pointed out, “You guys dry-humped though,” Kristin grinned and admitted, “Yeah, we did.” She joked about the revelation: “When this comes out, I had nothing to fucking do with it!”

Kristin Cavallari’s Dating History: Glen Powell, Brody Jenner, Morgan Wallen, Jason Statham

Image Credit: Getty

Image Credit: Getty

We’d be here all month if I described Kristin’s entire dating history in detail, but I feel it’s necessary to refresh you on some of the wilder names. Before her Glen hookup, Kristin was linked to several characters, including nepo son x reality star Brody Jenner back in 2005. In a TikTok video, Kristin’s BFF, Justin, also revealed that she hooked up with Jason Statham at some point. He referred to Jason as Kristin’s “hottest hookup,” which seems accurate.

Kristin was married to Chicago Bears quarterback Jay Cutler from 2013 to 2022, and they share three kids together. Following their split, I fear she was involved with country star Morgan Wallen. She claimed he was “good in bed”… I find that hard to believe. Recently, Kristin dated former NHL player Nate Thompson. She called their romance “the most honest, pure, amazing, quote-unquote relationship I’ve ever had.”