Lane Kiffin and Layla Kiffin’s 12-year marriage ended in 2016 when the couple filed for divorce. Even after the separation, they stayed connected to raise their three kids. Now, it looks like during their time apart, Lane and Layla were actually on extremely good terms. He went to the extent of helping her find love like a true gentleman.

When the Ole Miss head coach was dating Sally Rychalk for four years, he was also trying to help Layla. Comedian Theo Von, who’s a close friend of Vandy QB Diego Pavia, revealed a strange story. “He was trying to set me up with his frea***g ex-wife,” Theo Von shares on his podcast, This Past Weekend. “Dude… He put us in a group chat, right? And then he’s like, I’ll leave you two alone. And he left the group chat. Oh, my God,” he added laughingly. “Welcome to the sip.”

Von has become a constant presence at the Kiffin abode. From attending concerts with Lane Kiffin to posing with Landry and cheering on Knox at his high school football game, Von shares a close bond with the family. Moreover, Van revealed what happened next.

“No, I didn’t, because I can’t really tell what’s going on, so I’m going to check in and see what’s up,” Theo added. “But yeah, that was just a crazy thing. He’s like, I’ll leave you two alone. And then he exited…” Overall, it was a crazy experience for Von, who remains a close friend to this day.

Although the exact timeline of the incident is unknown, one thing is clear: Layla and Kiffin had close contact after the divorce.

Since then, the couple has reconciled, with Layla constantly cheering on Kiffin from the sidelines. However, their love life hadn’t always been smooth sailing.

It was in the 1990s that the duo met through Layla’s father, John Reaves, a former NFL quarterback. They soon began their courtship and were married in 2004. Welcoming three wonderful children, Landry, Presley, and Knox, the Kiffins became a family of five, while the young coach went on to achieve success in his coaching career. However, things didn’t go perfectly.

After 12 years of marriage, the couple filed for divorce in 2016 because of irreconcilable differences; yet, they maintained an amicable relationship. Over time, both of them moved on with their lives. Kiffin had started dating Sally Rychalk while maintaining a friendly relationship with Layla. Although Von didn’t shoot his shot, there’s no public information available about whether Layla ever dated anyone after the divorce.

Lane and Sally parted ways in the fall of 2024. Soon after that, he and Layla reconciled, putting aside their differences. Over Christmas last year, Coach dropped hints regarding their renewed relationship. Posting a picture of Layla with both his daughters, Landry and Presley, rocking matching hats, he wrote, “It’s beginning to look a lot like Christmas.” Later, the speculations found solid ground when he shared snaps from Layla’s 51st birthday dinner.  

Presently, the Kiffins are a contented family. Layla and the children are often present at the Ole Miss campus, cheering for him. Among the many faces, Von Theo is another member whose frequent appearances suggest a close bond with the Kiffin family.

Theo Von cheers for Knox along with the Kiffins

Friday marked a wholesome occasion for the Kiffins. Youngest Knox, a Class of 2028 quarterback at Oxford High, led the Chargers to a 42-6 win, taking his school to the 7A state playoffs. Over the stands, a proud dad in Lane Kiffin beamed brightly, flanked by Landry and Theo Von. Star quarterback Trinidad Chambliss also accompanied the fam, as Knox threw for 93 yards and completed two touchdown passes.

Over the sidelines, his dad and Chambliss were flanked by an equally excited Theo, who had a three-word reaction to Knox’s electric performance. “Fire US UP.” His attendance at the Stadium wasn’t the only time Theo appeared around Kiffin.

Back in October, Von further dined out with the family, pointing to his strong, friendly relationship with Layla and Lane. “Happened to be at dinner with Theo (Von), and then he walked us next door. Went into a concert for a little bit,” Coach shared. “It was pretty cool.” It was the Lainey Wilson concert that took place at Nashville’s Bridgestone Arena.

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Following this, Theo shared a snap with Coach Kiffin, posing with a peace-out sign, “Lainey show w my new sponsor @Lane_Kiffin.”