Ryan Cabrera was ‘jealous’ of ex Ashlee Simpson’s boyfriends before their romance: ‘I always had a crush’

Emlyn TravisThu, August 27, 2026 at 8:01 PM UTC

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Ashlee Simpson and Ryan CabreraCredit: Mark Sullivan/WireImageKey Points -

Ryan Cabrera says he was “jealous” of ex-girlfriend Ashlee Simpson’s boyfriends before the musicians started dating.

The couple’s relationship was featured on the first season of Simpson’s reality show, The Ashlee Simpson Show.

The two remain good friends more than two decades after their split in 2005.

Ryan Cabrera was crushing on Ashlee Simpson long before they ever began dating.

The “On the Way Down” singer, 44, revealed on a recent episode of Danielle Fishel’s Teen Beat podcast that he was “jealous” of Simpson’s previous boyfriends prior to them becoming an item in 2004. Cabrera briefly lived with Simpson, 41, and her family after her dad, Joe, discovered him at a Dallas gig and helped him move to Los Angeles.

“I was just a kid with big eyes and just stoked to be here and, next thing I know, Ashlee’s my neighbor,” he recalled. “I would go run by and play her songs and I always had a crush on her, but we weren’t dating at the time. She was with somebody else. But I would go into her room and play her songs and stuff and be kind of jealous of the dudes that she would have over.”

Ashlee Simpson and Ryan CabreraCredit: Jeff Vespa/WireImage

Sparks didn’t fly between the pair until after they starred in Cabrera’s “On the Way Down” music video.

“We had to kiss in the video. I remember being super nervous,” he admitted. “We kissed in the video and then that night, we ended up on the dance floor in a club. And then we’re like, ‘Well, this is weird… We’re like roommates. We live in the same house now.’”

From there, the couple’s relationship was famously depicted on the first season of Simpson’s eponymous reality show, The Ashlee Simpson Show. “They just followed us around,” Cabrera said. “That kind of was the birth of our relationship and us as artists.”

He also reminded Fishel that Simpson’s show was released during a time when “reality TV was real.”

“There was no storylines,” Cabrera added. “There was no like, ‘Okay, here’s who you have to talk about. Here’s what you gotta do.’ It was cameras around us and we didn’t pay attention and we were actually ourselves on that show.”

Cabrera continued, “So when I look back at that, it was a fun time. ‘Cause I was just like, that was just us being us.”

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The couple ultimately went their separate ways in 2005, after several months of dating. In the years since, both stars have gone on to find love again.

Simpson has been married to fellow actor and musician Evan Ross since 2014, and the couple shares two children: Jagger, 11, and Ziggy, 5. The “Pieces of Me” singer is also mom to son Bronx, 17, whom she shares with her ex-husband and Fall Out Boy bassist Pete Wentz.

Cabrera, meanwhile, tied the knot with WWE professional wrestler Alexa Bliss, a.k.a Alexis Kaufman, in 2022. They welcomed their first child together, daughter Hendrix, the following year.

To this day, Cabrera and Simpson remain good friends. Speaking with PEOPLE last December, Cabrera revealed that she and Ross attended his wedding.

“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 at the time. “Everyone’s got a beautiful family now. We’ve all grown up and get to see everybody thriving, and we love that.”

He continued, “It’s a very fun, happy, healthy environment. And it’s exciting when you can see somebody from your past and root for them and watch them do well.”

Listen to Cabrera discuss his and Simpson’s romance in the clip above.

on Entertainment Weekly

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