Back in 2004, Ashlee Simpson and Ryan Cabrera were one of the hottest couples in the music world. Ashlee’s father Joe Simpson was managing Ryan Cabrera and Ashlee was recording music of her own.

Unfortunately the relationship didn’t work out. Both Simpson and Cabrera went on to have fairly successful music careers, even after going their separate ways.

Ashlee’s hit song Pieces Of Me was dedicated to Ryan and Ryan’s song Photo was dedicated to Ashley.

At the time they were dating, Ashlee was starring on her reality show The Ashlee Simpson Show. Ryan made several appearances on the show.

Ryan Cabrera is no longer managed by Ashlee’s father and Ashlee is currently engaged to Evan Ross, the son of singer Diana Ross.

What an amazing engagement party with all of our loved ones! We gettin' married 🙂 pic.twitter.com/xdQLFerlIk

— Ashlee Simpson (@ashleesimpson) March 27, 2014

My baby love and I are ENGAGED!!! Hallelujah Hawaii !!!!! pic.twitter.com/KVwoltverE

— Ashlee Simpson (@ashleesimpson) January 14, 2014

Although Ashlee and Ryan couldn’t get their romantic relationship to work out, they are still really good friends.

Ashlee and Evan both recently attended Ryan’s birthday party and all three of the stars socialized together and even talked music.

A source at the party said,

“They were both super cute with one another, very affectionate and very touchy feely. At one point Ashlee even had Evan sitting on her lap as they conversed with their friends.”

Ashley also asked Ryan if he would play his new record for Evan and asked Evan to give Ryan some feedback.

Evan liked Ryan’s music and the two even talked about collaborating on some songs in the near future.

Perhaps they can write a song about Ashlee together.

What do you think of Ashlee’s relationship with her ex-boyfriend Ryan Cabrera and do you think her fiancé Evan is comfortable being around him?

Image via Wikimedia Commons