It’s been over twenty years since Ryan Cabrera and Ashlee Simpson were an item—but fans can rest easy knowing the former couple has nothing but goodwill toward each other.
Back in 2004, Ryan, 43, and Ashlee, 41, were dating, and he even appeared on her MTV reality show The Ashlee Simpson Show. These days, both have moved on with families of their own, yet Ryan says the connections remain strong.
“We’re definitely friendly,” Ryan told People. “My wife [Alexa Bliss] loves her.”
He also highlighted that his friendship extends beyond just Ashlee. “Me and Ashlee‘s husband Evan Ross have been friends for a long time,” he added, noting that he’s still close with Ashlee’s mom, Tina Simpson.
“I still pop by and see her mom at the showroom and they have presents for Hendrix, our daughter,” he shared. “Everybody just roots for each other.”
Ryan emphasized that the past doesn’t carry bitterness. “We have such a great history and nobody has anything bad to say about each other because we’re all just happy that everybody’s happy,” he said. “Everyone’s got a beautiful family now. We’ve all grown up and get to see everybody thriving, and we love that.”
The families even intersected in celebratory moments. Ryan recalled that Ashlee and Evan attended his April 2022 wedding to Alexa. “It’s a very fun, happy, healthy environment,” he said. “And it’s exciting when you can see somebody from your past and root for them and watch them do well.”
For fans of early-2000s pop culture, it’s a heartwarming reminder that sometimes, former flames can stay allies in life, proving that time, maturity, and perspective can turn old relationships into supportive friendships.
