Inside Kristin Cavallari's Life Now: Successful Coparenting and...Dinners With Stephen Colletti?!

Had we been looking for a sign about how Kristin Cavallari is handling her split from husband Jay Cutler, we got it in the form of her night out with Laguna Beach love Steepheennn.

By Sarah Grossbart Aug 10, 2020 7:00 AMTags
Watch: Kristin Cavallari & Stephen Colletti's Cozy Reunion

When Kristin Cavallari posted her latest snap to Instagram Aug. 4, Laguna Beach fans the world over had the same collective reaction: Stephen? Steepheeennn?!

It wasn't just that the newly single lifestyle mogul had her arms draped around her former high school sweetheart Stephen Colletti, her costar on the early 2000s MTV obsession, or that the exes had the look of two coconspirators sharing in a delicious secret. It was also the winking, intentionally vague caption, the onetime reality TV villain writing, "2004 or 2020?!" 

Uh, WHAT? 

In the spotlight since MTV producers singled out the high school junior, her then-boyfriend and their circle of pals to portray what they were marketing as the real Orange County (a nod to Fox's can't miss teen drama, The O.C.), Cavallari is certainly savvy enough to know the sort of chatter such a cozy picture would spark. Some 550,000 double-tapped to show their appreciation, more than a few of them—including fellow network standouts Snooki and Angelina Pivarnik—taking to the comment section to reiterate that they were here for this re-coupling. 

As Cavallari's pal Steph Biegel effectively summed up, "This. is. EVERYTHING."

Looking Back at Kristin Cavallari's Star-Studded Dating History

Well, not everything. The post was not, in fact, an announcement that the 33-year-old is rekindling things with her teenage ex, a source telling E! News, "They are not dating." 

But it certainly is a sign that the Uncommon James founder is rebounding quite nicely from her April split with husband of nearly seven years, Jay Cutler. While the retired NFL quarterback, 37, has taken himself out of the game, deleting his Instagram account shortly after Cavallari's throwback Tuesday, the cookbook author has returned to her true roots, giving us all a glimpse at her life. 


She's filling her days with work—'gramming her May 26 return to the UJ offices and prepping for the September release of her second collection of recipes, True Comfort— and tending to her "tribe": sons Camden, 8, and Jaxon, 6, and daughter Saylor, 4.

And she's finding time for nights with her squad. Months after their unintentional  March quarantine getaway in the Bahamas, Cavallari's hairstylist bestie Justin Anderson remains her number one, the pals bunking up before the designer moved into her new $5 million Nashville digs. "We've been together for the entire quarantine time," she shared in a May Instagram Live chat, "literally from day one."

Trips out west have afforded her the chance to catch up with other pals, too. "Kristin was excited to have a getaway in Los Angeles," a source tells E! News of her June excursion, "and it's been a fresh breath of air to be able to go out and see her friends." That includes Colletti, the duo meeting up during Cavallari's most recent vacation to southern California. 


As for the other man in Cavallari's life, she and Cutler seem to have found their conscious uncoupling footing, trading heartfelt sentiments on Mother's Day and Father's Day. The former Chicago Bears leader even gave her upcoming cookbook a plug, in a July Instagram story, calling the dishes "taste tested and approved." 

Though an insider predicts it could take them awhile to sort through the details of their divorce, they've already untangled one potentially knotty issue, each agreeing to a week-on, week-off shared custody arrangement. "Modern family? Co-parenting?" Cavallari wrote in her Father's Day tribute. "Whatever you want to call it, we are navigating it the best way we know how."

Timothy Hiatt/Getty Images

They've already proven to be quick studies, a source telling E! News they are "in a much better place" than in the still-painful weeks immediately following their April divorce announcement. "Everything has definitely settled between them and there is less tension."

Still left are heaps of hope for the future that lies ahead. "She is doing much better and seems to be very happy," continues the source. "Kristin knows this is the right choice for her family and she is excited for a fresh start."

Of course, she's not the only one staring at a blank page before her...

With such a major Laguna reunion taking place (well, two, actually, Cavallari also meeting up with Alex Murrel Johnson during her current California trip), now feels like a good time to check in with both the OG cast and the onetime Les Deux frequenters from the initial run of The Hills. Here's what they've written so far. 

Lauren Conrad

Literal LOL at Teen Vogue's Lisa Love telling Lauren, "You'll always be known as the girl who didn't go to Paris." (A line actually lifted from Vogue's Anna Wintour, a 2019 Hills deep dive revealed.) More than a decade after that (admittedly questionable) decision and her subsequent split from Jason Wahler, LC has earned a few more laudatory descriptors: New York Times best-selling author; co-founder of The Little Market, with a mission to empower female artisans worldwide; and, of course, fashion designer, her Kohl's Line LC  Lauren Conrad just the start of her now wide-ranging lifestyle empire. Now long past fights outside Les Deux, she married Something Corporate rocker and law school grad William Tell in a 2014 Pinterest wedding of our dreams. In 2019, their second son, Charlie Wolf Tell, joined older brother Liam James Tell

Kristin Cavallari

The star of E!'s Very Cavallari and everyone's favorite bad girl went from being a (well-compensated) s--t-stirrer to full-on boss with her successful lifestyle brand, Uncommon James opening its second brick-and-mortar location in Chicago last fall. Rounding out her growing empire: a Chinese Laundry shoe line and two cookbooks, with True Comfort coming out Sept. 29, a little more than two years after New York Times best-seller, True Roots.

Teammates for 10 years, she and retired NFL quarterback Jay Cutler welcomed sons Camden Jack Cutler and Jaxon Wyatt Cutler and daughter Saylor James Cutler before splitting in April 2020.

In 2021, Kristin filmed a cameo for The Hills: New Beginnings season two.

Heidi Montag & Spencer Pratt

One of the more surprising reinventions saw The Hills' resident villains transform into dedicated parents to 2-year-old Gunner Stone Pratt, entirely self-aware of their place in the annals of reality television. Following an admittedly rocky season that saw them take their marital problems (either real or contrived for headlines) to any show that would have them—Celebrity Big Brother (UK version), I'm a Celebrity . . . Get Me Out of HereMarriage Boot Camp: Reality Stars—they successfully lobbied to make Speidi famous again, spearheading 2019's The Hills: New Beginnings reboot. "Reality TV is kind of a career for Spencer and I at this point," Heidi explained to Vogue. Though, having learned from their years of overspending, they also have a few side hustles thanks to their podcast and his Pratt Daddy crystal business.  

Lo Bosworth

Truthfully, LC's BFF would prefer to be excluded from this narrative. When an exec gauged her interest in returning to The Hills, "I was like, 'F--k no!'" she recalled on a 2018 episode of her Lady Lovin' podcast. "I don't want any association with any of those people. The dissociation from all those people is what I'm hungry for." Which, to be fair, sometimes that happens when you change careers. Now based in NYC, The International Culinary Center grad and The Lo-Down author founded Love Wellness, a line of personal care products for women, in 2016. In 2020, she told E! News, "I live such a different life now than I did 10 years ago."

In March 2021, Lo shocked fans when she revealed on Instagram that she had secretly suffered a traumatic brain injury in an accident two years prior. 

Brody Jenner

His original stint on The Hills saw him juggling purported romances with both Lauren and Kristin and set the tone for the interest in his love life that would continue even after he stepped off camera to lean into his work as a DJ. (His 2015 E! series Sex With Brody may not have helped things.) Though it appeared he'd found his forever when he wed now-Hills costar Kaitlynn Carter in a 2018 Indonesian ceremony, the two ended their romance in 2019. He's gone on to date TikTok star Daisy Keech, model Josie Canseco and Briana JungwirthLouis Tomlinson's ex.

Audrina Patridge

A reality TV pro at this point, Lauren and Heidi's camera-ready neighbor followed up her Hills gig with a 2010 spin through the Dancing With the Stars ballroom, her own VH1 series, Audrina and a short-lived hosting stint on NBC's traveling series 1st Look. Now back on MTV with Speidi, Brody, et. al, she also dove into the world of designing with her Prey Swim line. And while she's dated after her messy divorce from BMX biker Corey Bohan, revisiting an old romance with Ryan Cabrera and sharing an entirely unsuccessful dinner date with Justin Bobby Brescia, her number one these days is daughter Kirra Max Bohan

Whitney Port

The girl who did go to Paris (except, not really, as she revealed to Vogue) enjoyed a brief stint in The City in 2008 before heading back to Los Angeles, with future husband Tim Rosenman, an associate producer on her NYC-based spinoff, in tow. A judge on the eighth cycle of Britain & Ireland's Next Top Model, she now juggles her Love, Whit line with Rent the Runway and With Whit podcast alongside her return to The Hills and her son Sonny Sanford Rosenman

Stephen Colletti

When he's not giving us new material for our LC-Kristen-Stephen love triangle fan fic, Laguna's resident heartthrob is focused on building a pretty solid acting career. He was a recurring castmember on the CW's One Tree Hill for five seasons and starred as Taylor Swift's love interest in her "White Horse" music video. He also had a temporary gig as an MTV VJ on Total Request Live (the original, not the reboot). In 2018m he appeared in the TV movie Hometown Christmas. In January 2021, he and OTH co-star James Lafferty debuted a Hulu series, Everyone Is Doing Great.

Jessica Smith

KCav's Laguna Beach pal has largely stayed away from reality television after her run on the MTV show ended. Following a brief return to notoriety, thanks to a 2007 DUI arrest, she settled into a quiet life in Texas with her husband, Michael Evans, "the most kind, patient, strong, amazing, loving and ridiculously handsome human I've ever met," as she put it on Instagram, and their four children. Though she has her own blog and Amazon shop, mostly, she jokes on Insta, she's "just trying not to lose a kid."

Jason Wahler

The resident bad boy of Laguna Beach and The Hills ran into nothing but trouble after his time on the reality series: drugs, DUIs, fights, arrests…you name it. It wasn't until he appeared on Celebrity Rehab with Dr. Drew Pinksy that he finally cleaned up. Wahler went on to marry girlfriend Ashley Slack, a relationship he claims is his first sober one, and he and "the most beautiful, loving, kind and caring woman I know" welcomed daughter Delilah Ray in August 2017. In February 2021, the couple revealed they are expecting their second child.

 The founder and owner of Widespread Recovery, he continues to be open about his struggles, both on The Hills: New Beginnings and his YouTube series, JAWS Diaries with Jason & Ashley Wahler

Stephanie Pratt

Originally brought in to face off with Lauren, she befriended her instead, leading to seemingly unending drama between Stephanie and brother Spencer. Following years across the pond appearing on UK reality fare such as Celebrity Big Brother and Made in Chelsea—and one 2015 memoir detailing her struggles with bulimia, crystal meth and staying out of trouble—she headed home to The resume stirring up drama. After a scathing takedown of her castmates (she labeled sister-in-law Heidi "evil" and Audrina "crazy"), Stephanie announced she won't be returning for season two.

Casey Reinhardt

Though she wasn't an original castmember of Laguna Beach, her arrival to the reality series was a memorable one. Since then, Casey launched a successful foray into the world of confections by opening Casey's Cupcakes in Orange County. She even won Food Network's Cupcake Wars in 2011. Her home life, meanwhile, is just as sweet. Wed to Sean Brown (a relative of the late Nicole Brown Simpson) since August 2015, they share daughter Kensington Kelly Brown and son Sean Brown Jr.

Dieter Schmitz

Lauren and Stephen's bestie left the Beach behind for his future in hospitality and hotel management, moving first to New York and, in 2019, to Washington, D.C. where he works as general manager of the Lore Group, leading the February opening of Riggs Washington DC. He's still tight with his high school crew, though, Lauren, "proud groomsman" Stephen, Trey Phillips, and Loren Polster turning out for his 2016 Monterey, Calif. wedding to Isabell Hiebl. The pair welcomed their first child, son Nico Josef Schmitz, in September 2018.