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Playing Catch-Up with Ashlee Simpson's First Love: Ryan Cabrera

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KMazur/WireImage

When it comes to Great Love, there’s Will and Kate. Romeo and Juliet. Taylor Swift and glitter.

But in 2004, it was Ashlee Simpson and Ryan Cabrera. Like a modern Jane Austen love story, she starred in his music video, and then their relationship played out on her MTV reality show. Even after the couple broke up, Simpson told press that she still considers Cabrera a “great guy.” (As you may recall, Simpson was also formerly married to Fall Out Boy bassist Pete Wentz, but that’s another love story.)

Yes, this Great Love was about a decade before Simpson announced Monday that she is engaged to Evan Ross, the actor and musician son of Diana Ross. And while we’re very happy for the soon-to-be newlyweds, we couldn’t help but wonder how Cabrera’s feeling right about now – or, better yet, what he’s up to. So we investigated.

Nobody panic: He’s still making music

Ryan Cabrera in the studio
Courtesy Ryan Cabrera
The singer, 31, regularly Tweets about his time in the studio, which is great news for anyone holding out for a proper follow-up to his debut single, “On the Way Down.”


He’s performing, too

Ryan Cabrera
Courtesy Ryan Cabrera
He’ll be taking the stage in Absecon, N.J., on Jan. 31 and Sellersville, Pa., on Feb. 1, if you need a fix before his fifth album comes out.

He paints all the time

Ryan Cabrera’s The Lion King painting
Courtesy Ryan Cabrera
The multi-talented artist regularly shows off his masterpieces on Instagram, which are often Disney-themed.

He likes to hang out with his dog

Ryan Cabrera and his dog Penny Lane
Courtesy Ryan Cabrera
Penny Lane, a rescued Coton de Tulear, even has her own Instagram account, because … fame.

And Lance Bass!

Ryan Cabrera and Lance Bass
Courtesy Ryan Cabrera
Cabrera stopped by Bass’s SiriusXM Radio last year, and, in other news, our teenage selves are retroactively hyperventilating.

And, basically, Ryan Gosling

Ryan Cabrera’s tattoo of Ryan Gosling
Starpicz/Splash News Online
Another famous Ryan’s face is inked on Cabrera’s leg, thanks to a game he plays with his friends called “tattoo roulette,” in which “we blindfold each other. ‘You get to pick a tattoo for me, and I get to pick a tattoo for you.’ And you don’t get to see it ’til they’re both done,” he told the Las Vegas Review-Journal. Still, he calls his permanent tribute to Mr. G “the Bentley of tattoos.” His latest ink addition: a pair of ballet slippers inscribed with the expression, “Dance like no one’s watching.”

We know everything’s going great for Ryan and Ashlee, but one more time with feeling

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