Ryan Phillippe was reliving his ‘90s heartthrob days when he shared a throwback photo of him and ex-wife Reese Witherspoon via his Instagram Story.

“We were hot and drenched in late ’90s angst,” Ryan, 49, wrote alongside the photo of him and Reese, 48, at the premiere of her hit movie Legally Blonde in 2001. “(so much cooler than today).”

In the picture, Reese wore a black and white striped halter dress while Ryan sported a mohawk hairstyle with a sleeveless collared shirt.

Ryan and Reese met at the Sweet Home Alabama star’s 21st birthday party in 1997, and she revealed she jokingly told him that she thought “he was her birthday present” in an interview with Jane magazine in 1998. The I Know What You Did Last Summer star proposed and after the couple went on to film their steamy 1999 hit, Cruel Intentions, they officially tied the knot in June 1999. Reese was around six months pregnant at the time and three months after they walked down the aisle, she gave birth to their first child, daughter Ava.

The Morning Show actress was only 23 years old when she gave birth, and she’s been open about how nerve-wracking it was for her and Ryan to be young parents.

“To be completely candid, I was terrified too,” Reese said during an appearance on The Drew Barrymore Show in 2020. “I got pregnant when I was 22 years old, and I didn’t know how to balance work and motherhood, you just do it. I was just like every other mom and dad trying to figure it out.”

Ryan Phillippe Gushes Over Reese Witherspoon in Throwback Pic
RJ Capak / Getty Images

However, it wasn’t long before Ryan and Reese’s relationship hit a rough patch, and Ryan admitted in 2002 that they were in couple’s therapy to the Daily News, per People. He told the outlet that the “biggest mistake” was to have a “marriage falling apart due to laziness.”

Reese also opened up about the couple’s work they put in toward their marriage around the same time.

“I’m not interested in the fallacy of the Hollywood relationship: ‘We have perfect children who never cry; we never have problems; we never argue, we’re always best friends,’” Reese told People. “That’s just not true. We’re normal people with normal problems.”

In October 2003, Ryan and Reese welcomed their second child, son Deacon. While the pair appeared happy, three years later they announced they were separating on October 30, 2006.

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the couple said at the time. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.”

Ryan called his split from Reese “the darkest, saddest place I’ve ever been” in an interview with W magazine in 2008. While rumors swirled that an alleged affair with Abbie Cornish led to his and Reese’s divorce, Ryan said that the real reason was “far more complicated.”

Despite calling it quits, the 54 star and Reese have remained friendly over the years, and they’re often seen celebrating milestones for their two children together.