Inside Kristin Cavallari and Jana Kramer’s Past, Surprising Connections

Credit: Willy Sanjuan/Invision/AP/Shutterstock; Debby Wong/Shutterstock

Inside Kristin Cavallari and Jana Kramer’s Past, Surprising Connections

Where are the reality TV cameras when you need them? After Jana Kramer was spotted on a date with Jay Cutler, Us Weekly is looking into the One Tree Hill alum’s past with Kristin Cavallari. Kramer and Cavallari have known each other for over a decade, appearing in 2009’s Spring Breakdown. The “I Got the Boy” singer and the Hills alum have since seen each other at events and supported their respective projects. “Love this sweet Momma. @kristincavallari,” Kramer captioned a pic of the pair at an event in 2018 via Instagram. Cavallari left a series of red heart emojis on the post. Fast-forward to 2021 and both Kramer and Cavallari are going through breakups. While the reality star is still trying to finalize her divorce from Cutler, whom she split from in April 2020 after seven years of marriage, the Lifetime actress split from Mike Caussin in April 2021 and their marriage was legally over as of that July. According to sources, Cavallari was there to support Kramer as she navigated the split and Caussin’s alleged cheating. When asked about Kramer in August 2021, Cavallari told Us Weekly, “I see Jana because we're both in Nashville, so we don't have to do Zooms. We can actually hang out.” [jwplayer 6r7J9Upj-l3ahXupL] Less than one month later, Kramer was spotted on a date with Cutler in Nashville. “Jay was trying to make Kristin jealous but Kristin has told friends it isn’t going to work,” a source close to Cavallari told Us at the time. “It’s not a coincidence that Jay decided to go public with Jana right after news broke that Kristin and Chase Rice are dating.” An insider close to Kramer, meanwhile, insisted that the twosome were never close. “Jana and Kristin have only met a few times in person at events for work. They were never friends,” the source said. “They supported each other’s projects here and there. Their kids have never met.” (Kramer and Caussin share daughter Jolie and son Jace, while Cavallari and Cutler are parents of sons Camden and Jaxon and daughter Saylor.) The first source added that Cavallari “blocked” Kramer on social media after the first date: “She wouldn’t have blocked her if she wasn’t good friends with her.” Scroll through for everything we know about Cavallari and Kramer’s dynamic and similarities:

Credit: Courtesy Jana Kramer/Instagram

Filming ‘Spring Breakdown’

While posing together at an event in 2018, Kramer touched on how they met. “Trivia: what was the movie we did together?!?!?” she captioned the snap, referring to the 2009 film Spring Breakdown.

Credit: Shutterstock (2)

Married to Ex NFL Players

While Cutler was a quarterback for the Chicago Bears and Miami Dolphins, Caussin played tight end for the Jacksonville Jaguars Buffalo Bills, Jacksonville Jaguars and Washington Redskins.

Credit: Shutterstock (2)

Living in Nashville

After leaving Tennessee because of “triggers” as Caussin was unfaithful in 2016, Kramer and her then-husband looked for a fresh start in Los Angeles. In 2019, however, they returned to Nashville. Cavallari and Cutler, meanwhile, moved to Nashville in 2017.

Credit: Shutterstock (2)

Divorce Lawyer

According to a source, the women used the same divorce lawyer for their respective split.

"Jana has been leaning on friends for support during her divorce,” a source told Us in April 2021. “Jana is using the same lawyer Kristin is using in her divorce so Kristin has a lot of advice to offer Jana, especially since it's been a year now. Jana and Kristin always chat about their kids and motherhood, so now Kristin can surely help her with single mom stuff since she already is a pro at this."

Another source added in September 2021, “Kristin's been helping Jana throughout her divorce.”

Credit: Courtesy Jana Kramer & Kristin Cavallari/Instagram

The Stephen Connection

Cavallari was infamously in a love triangle with Stephen Colletti and Lauren Conrad during their time on Laguna Beach in the early 2000s. After becoming an actor, Colletti played Chase Adams on One Tree Hill for several years. During season 8 of the CW show, Kramer’s Alex Dupree dated Chase. Both women are still friendly with Colletti. 

Credit: Shutterstock (3)

Dating Jay

Multiple sources confirmed to Us in September 2021 that Kramer was spotted on a date with Cutler. "Jana is the complete opposite of Jay's ideal girl. She puts her kids on social media and shares a lot of her personal life with her fans — she's just not the typical girl Jay would date,” a source told Us at the time.

Credit: Drew Altizer Photography/Shutterstock; Sara Jaye Weiss/Shutterstock; Mark Humphrey/AP/Shutterstock

Jana Speaks

When asked about headlines surrounding her relationship with Cavallari in September 2021, Kramer didn’t deny that their friendship was strained.

"I know my truth, I know my heart, I know the person that I am, and I can go to bed knowing those things," she told Entertainment Tonight. ”I don't feel like I have to defend — I don't wanna defend myself anymore. I know who I am, I know my intentions in my heart, and I have respect for everybody involved, so as long as I do things the right way, then I'll be OK.”