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 […]
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.
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.
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Following Simpson and Cabrera’s breakup, Simpson went on to date her ex’s close friend Evan Ross.
In an interview with TooFab, 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.
“But we remained friends, like, very shortly after we broke up, and then remained friends from that point on. And we were always cool.”
Ross, 33, and Simpson ended up getting married in August 2014.
The couple began dating in 2013, almost 10 years after she split with Cabrera.
Their wedding took place in Greenwich, Connecticut US Weekly reports.
They now have three children together: Bronx Wentz, Ziggy Blu Ross, and Jagger Snow Ross.
Simpson shares her son Bronx with her ex-husband Pete Wentz to whom she was married from 2008 to 2011.
Simpson spoke to PEOPLE in 2021 about Ziggy, the family’s newest addition.
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“He’s got a real sweet personality so he’s a real hit.
“Jagger loves to entertain him. She likes to sing and dance for him,” she said.
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