Everything kicked off in Oct. 2020, when, according to Austen Kroll, Kristin Cavallari slid into Craig Conover's DMs.
"[She] was like, 'I'm coming into town,' so we all went to dinner," Austen said on Watch What Happens Live in December of that year, explaining that Kristin was joined on the trip by her longtime friend Justin Anderson. "We all kinda hit it off. We wanted to go and visit them, and we did. We all get along so well."
Austen was seemingly still together with his on-again, off-again girlfriend of nearly three years Madison LeCroy in November, however, fans were thrown off by a comment she left on a photo shared by none other than Kristin's ex, Jay Cutler, over Thanksgiving weekend.
"See y'all soon!" Madison wrote on the pic, which, to make matters even more confusing, featured Shannon Ford, Kristin's ex-friend who she famously fired on the season two premiere of E!'s Very Cavallari.
Austen left what seemed to be a flirty comment on a bikini photo posted by Kristin on Dec. 6, writing, "See you next week! Keep breaking the internet in the meantime."
However, when Comments by Bravo shared a screengrab of Austen's remark that same day, Madison shut down speculation by replying, "Yeah trust me if he was with her he wouldn't be sending me songs at midnight...last night."
One day after the Instagram drama, Madison LeCroy told Us she was "1,000 percent single."
"And so is he," she added of Austen in the Dec. 7 interview. "So, ladies, if you want him, you can have him."
Kristin, Austen, Craig and Justin Anderson had a night out in Nashville and documented the fun on their respective Instagrams, with one video showing Kristin on Austen's shoulders. The next day, Dec. 14, she seemingly addressed any romantic speculation in an Instagram Story captioned, "I didn't realize I wasn't allowed to have FRIENDS that are guys."
A lot went down in the days between December and February 2021—Kristin became involved with comedian Jeff Dye, and Madison was rumored to be dating Jay one minute and then Alex Rodriguez the next—but Kristin, Austen and Craig once again shut down any romantic speculation during the Southern Charm stars' podcast on Feb. 9.
Addressing how she messaged Craig all those months ago, Kristin explained, "So I DM'd you, slid into the DMs, and said thank you for the masks, we're coming to Charleston in a month or whatever it was. I was like I think we're all going to hang out because you guys already had this connection with Justin. It wasn't romantic, it wasn't flirty."
"No one hooked up with anyone," Kristin added. "Nothing ever happened. We had a really good time."
Craig and Summer House's Paige DeSorbo became the subject of speculation in April after they were rumored to have been displaying PDA while hanging out in Charleston (nobody knew it at the time, but the pair had recently been filming Bravo's Winter House).
However, Paige set the record straight on April 20. "Craig and I are a thousand percent not dating," she said on the Not Skinny But Not Fat podcast. "Craig and I have known each other for years. We've always gotten along. We've always been friends. We have, like, very similar personalities. We are not romantically involved or anything, but we are very good friends."
Kristin spent a weekend in Charleston with pal Steph Biegel and—yep, you guessed it—Craig and Austen in June 2021.
Once again making it clear that she's not involved with Austen or Craig, Kristin shared an Instagram Story that read, "I haven't been involved in a love triangle since I was in high school."
This particular post is important, though, as it was shared around the same time Summer House season six was filming.
Winter House premiered in the fall, and while there was no on-screen romance between Craig and Paige unfolding, they had already started to become more than friends once filming wrapped. By October, they were official.
As Austen told E! News on Oct. 18, "It's something that I thought was going to happen in the house but Craig had a girlfriend...I for sure saw this happening."
Summer House star Amanda Batula gave the new couple her stamp of approval around the same time. "I love them together!" she said. "I think it's really, really cute and seeing them together just makes me smile all the time."
Paige and Craig were still going strong in late November and celebrated the holidays with one another. E! News' Morgan Stewart asked Paige on Nov. 24 if she could see them getting engaged in the future, to which she replied, "I mean, we have only been dating for a couple of months, but if I can trick him into a diamond ring, I'm going to do it!"
Season six of Summer House premiered in Jan. 2022, and it didn't take long for the events of the past year to come up. On the Jan. 30 episode, Lindsay Hubbard shocked everyone—including Paige—by revealing that it was Craig, not Austen, who had been hooking up with Kristin after the group became friends.
While Craig wasn't thrilled to have to discuss the matter, he seemingly confirmed that he and Kristin had been more than friends at one point, saying, "I've hooked up with her before," and that Austen, "hates that I was making out [with Kristin]."
The Kristin situation has been discussed on several episodes of Summer House at this point, but she has yet to publicly address any of it. Nevertheless, the Feb. 14 episode was particularly enlightening, as Paige revealed details of Craig's alleged texts with Kristin.
"I guess she texted him like, 'You are not going to make me look like an idiot with her,'" Paige told co-star Ciara Miller. "And like, 'If you want her, like, go have her. Just don't make me look stupid."
Craig then referenced Kristin's July Instagram Story about never being in a love triangle with him and Austen. "And he [Craig] was like, 'OK, but you went on Instagram and lied,'" Paige said. "Like, 'You can't say you [Kristin] were never going to date either of us. We f--ked.'"
In an exclusive interview with E! News, Craig said he "felt terrible" Kristin got name-dropped on Summer House. "We had a great relationship and I thought it was really, really unfair that she was thrown into a show that she's not on," Craig said of Kristin, explaining that he was particularly upset with Lindsay Hubbard for being the one to mention her on camera. "Lindsay did it for TV. Everyone in our lives knew about that."
In March, Craig also gave an update about him and Paige, who, despite the year-old drama that was playing out on Summer House at the time, are doing great. "We openly dated around until it just got to the point where, you know, you like one person so much that you don't want to do that anymore," Craig told E! News. The couple is now "having a lot of fun and spending more time with each other," he added, "and just happy."
Paige will be spending a portion of her summer in the South! Craig told BravoTV.com that she plans to live with him in Charleston throughout the months of May and June.