Back To The Beach With Kristin and Stephen. Jason's womanizing ways were first introduced during the shows second season after two-thirds of season ones love triangle, Lauren "LC" Conrad and Stephen Colletti, moved to San Francisco to start college. That's when Kristin Cavallari took ownership of queen bee status at Laguna Beach High School while mostly commanding her best friend Jessica Smith's relationship with Jason who was often seen flirting with girls in other cliques. Jason's incessant style of looking like James Dean or Marlon Brando in a plain white tee did not do him any favors with his rebellious reputation. The inflection in Kristin's voice when she says, "Jessica," at any mention of Jason's name from the lovelorn teens mouth can still be heard today.
In season 2, episode 2, "You Can't Trust Him," Kristin, Jessica and Alex Hooser are driving around contemplating if Jason is cheating on Jessica. They joke that fashion show benefit that LC had organized right in front of her, but he was "still sorry."
According to E! News, Jason had stopped by the podcast after taking notice of both Kristin and Jason's Instagram posts of the same photo, which included Stephen as well. The Very Cavallari star captioned the photo, "Shenanigans," outside of her Nashville estate. Jason leaned into his bad boy persona, captioning his post, "up to no good...." The female focused podcast network Dear Media has ordered the 40 episode rewatch series featuring the ex-lovers Kristin and Stephen as they recount the series which ran on MTV for three seasons from September 2004 to November 2006.
Kristin, Stephen and Jason would all appear in different capacities on LC's spin-off series The Hills: New Beginnings, which was canceled after two seasons in January 2022. The former bad boy has struggled with addiction to alcohol having also appeared on Celebrity Rehab With Dr. Drew season 4 in 2010. He's remained committed to sobriety, detailing his personal journey with recovery after relapse on his website. Jason married hairstylist Ashley Slack in 2013 and have since welcomed two children in 2017 and 2021.
According to mainstream stars such as LC, Kristin, Lo Bosworth and Lexie Contursi; Back To The Beach With Kristin and Stephen could decide to highlight the eclectic talents of all its strong female cast who exited the series. If anything, hopefully Jason takes this opportunity to apologize for being a womanizer.
Source: E! News, Kristin Cavallari/Instagram, Jason Wahler/Instagram, Dear Media