When did Ryan Cabrera and Ashlee Simpson date?

ASHLEE Simpson is a singer who dated Ryan Cabrera before marrying her husband.

Ryan Cabrera and Ashlee Simpson were a Hollywood item prior to her marriage to Evan Ross.

When did Ryan Cabrera and Ashlee Simpson date?

Simpson, 37, and Cabrera, 39, were together over ten years ago in 2004.

The two reportedly dated for about a year before they called it quits.

Their relationship was documented on MTV's Ashlee Simpson Show.

That same year Simpson was featured in Cabrera's music video for his song On the Way Down.

What did Ryan Cabrera say about Evan Ross?

Following Simpson and Cabrera's breakup, Simpson went on to date her ex's close friend Evan Ross.

In an interview with , Cabrera revealed that Ross asked for his friend's approval before asking out Simpson.

"I happened to be asleep at the time," Cabrera said in 2019.

"He specifically came to my house to come have a chat and be like, ‘Yo, I wanted to see what you thought about it. Is everything good?’ He knew that I’d be, like, ‘Oh! All right, cool.’"

He went on to add that he was happy for the pair and is "great friends" with his ex.

"She ended up marrying one of my best friends," Cabrera said.

"How it all happened? Who knows. … L.A. and us all as artists and singers and actors and entertainers essentially, it’s a very small family.

"Obviously, everybody knows everybody, for the most part. And me and Ashlee were always really, really close. Like, our breakup was pretty … pretty, pretty smooth — other than a couple of things.