Monday, July 27, 2026

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Evan Ross asked permission to date Ashlee Simpson

Evan Ross asked Ashlee Simpson’s ex-boyfriend for permission to date her.
The 30-year-old actor and musician married Ashlee – with whom he has three-year-old daughter Jagger – in 2014, but her former boyfriend Ryan Cabrera has revealed Evan came to his house to ask if it was okay for him to start dating the singer.
Ryan, 36, explained: "I happened to be asleep at the time. 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.’"
The singer-songwriter has remained close with Ashlee, 34, since their split and is "best friends" with Evan, so says they’ve all "remained friends".
Speaking to TooFab, Ryan added: "She ended up marrying one of my best friends. 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. But we remained friends, like, very shortly after we broke up, and then remained friends from that point on. And we were always cool."
Meanwhile, Ashlee – who also has 10-year-old son Bronx with ex-husband Pete Wentz – recently said she was experiencing baby fever after her sister Jessica Simpson gave birth to her daughter Birdie in March.
The ‘Ashlee + Evan’ star said: "I’m not pregnant, but it definitely gave me the fever a little bit."
The ‘Pieces of Me’ hitmaker said baby Birdie is "so cute", and revealed Jessica’s other two children – Maxwell, six, and Ace, five – are already doting on their little sister.
Ashlee added: "Oh my gosh, she is so cute. Little Birdie. The kids were so cute – Jessica’s kids with their little baby sister."

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