06:34 PM EDT 10/09/2014

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Ashlee Simpson

Credit: Courtesy Jessica Simpson
Sister Act! See Jessica Simpson Celebrate Ashlee's Engagement 

Jessica Simpson Poses with Ashlee Simpson & Fiancé Evan Ross

Originally posted 01/15/2014 05:00PM

Jessica Simpson joined Instagram Tuesday, and she's already using it to spread some sisterly love. 

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Credit: Courtesy Neil Lane; Inset: Jon Kopaloff/FilmMagic
Ashlee Simpson's Engagement Ring: All the Details From Neil Lane Himself

Ashlee Simpson's Engagement Ring: All the Details From Neil Lane Himself

Originally posted 01/14/2014 06:00PM

Get a close up photo and all the scoop on the star's gold-and-ruby ring from Evan Ross

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Credit: KMazur/WireImage
Where Is He Now: Ashlee Simpson's First Love, Ryan Cabrera | Ashlee Simpson, Ryan Cabrera

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

Originally posted 01/14/2014 01:00PM

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.

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Credit: Jon Kopaloff/Filmmagic
Ashlee Simpson Is Engaged to Evan Ross

Ashlee Simpson Engaged to Evan Ross

Originally posted 01/13/2014 07:40PM

Ashlee Simpson is hearing wedding bells!

The singer, 29, is engaged to actor Evan Ross, the couple announced via Twitter on Monday.

"The love of my life said YES!!!!!!" Ross, 25, wrote, sharing a photo of the couple. Adds Simpson, "My baby love and I are ENGAGED!!! Hallelujah Hawaii!!!"

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Credit: Jamie McCarthy/Getty
Jessica Simpson's Kids Steal the Show at a Fashion Event in Dallas

UpdatePosted 11/24/2013 07:45PM

Jessica Simpson's Kids Steal the Show at a Fashion Event in Dallas

Originally posted 11/24/2013 05:15PM

For Jessica Simpson, this weekend's homecoming was a fashionable family affair.

Son Ace Knute, 4 12 months, adorably made his red carpet debut Saturday at a Dillard's store in Dallas during an event celebrating her Jessica Simpson Collection.

Simpson, 33, protectively held on to the chubby-cheeked infant, who looked sweetly stylish in head-to-toe gray, including an unbuttoned shirt with the sleeves rolled up and super-cool baby Jordan sneakers.

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Credit: Jamie McCarthy/Getty
Evan Ross: 'I'm So In Love' with Ashlee Simpson | Ashlee Simpson

Evan Ross: 'I'm So In Love' with Ashlee Simpson

Originally posted 11/19/2013 08:00PM

They haven't been dating for very long, but Evan Ross says that he and girlfriend Ashlee Simpson are crazy about each other.

"I'm so in love and we've got amazing things going on," Ross, 25, said at Monday's premiere of The Hunger Games: Catching Fire.

"And we inspire each other," the actor told omg! Insider.

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Credit: Pacific Coast News
PHOTO: Jessica Simpson Stuns in Little Black Dress

Jessica Simpson Stuns in Little Black Dress

Originally posted 11/03/2013 06:00PM

That's one hot momma!

Jessica Simpson and her fiancé Eric Johnson stepped out for a triple date on Thursday with sister Ashlee Simpson, her boyfriend Evan Ross, best friend CaCee Cobb and her husband, Donald Faison – but Jessica's figure stole the spotlight.

Wearing a curve-hugging black dress with her straight blond locks parted down the middle, a glowing Jessica held tight to Johnson's arm as the couple made their way past photographers in Los Angeles.

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Liam Hemsworth Helps Ashlee Simpson Celebrate Her Birthday in Atlanta

Caught in the Act

Liam Hemsworth Helps Ashlee Simpson Celebrate Her Birthday in Atlanta

Originally posted 10/09/2013 06:00AM

Happy birthday!

Ashlee Simpson joined boyfriend Evan Ross over the weekend to celebrate her 29th birthday in Atlanta.

Simpson, whose actual birthday is Oct. 3, Ross and a group of 10 guests gathered Saturday for a late dinner around 9:30 p.m at Buckhead hotspot Umi, where they enjoyed nigiri, sushi rolls, sashimi, rock shrimp tempura and miso-marinated black cod.

Ross is in Atlanta filming the final installment of the Hunger Games franchise, Mockingjay, and was joined by his costar Wes Chatham, Jovar Andrews (who was also celebrating his birthday) and DJ Rukus.

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Credit: AKM-GSI
Ashlee & Her Men: Simpson and Beau Evan Ross Stroll with Bronx | Ashlee Simpson

Ashlee Simpson Holds Hands with Evan Ross & Bronx

Originally posted 08/08/2013 01:30PM

Looks like things are getting serious.

Just one day after Ashlee Simpson bonded with new beau Evan Ross's clan – after mom Diana Ross's performance at the Hollywood Bowl – the new couple was spotted spending quality time with the other man in Simpson's life: Bronx Mowgli, her 4½-year-old son with ex-husband, Pete Wentz.

The trio was snapped holding hands in Venice Beach, Calif., on Sunday while sporting black rock 'n roll T-shirts. (From the looks of it, both mom and son paid homage to Michael Jackson, while Ross gave a nod to the Ramones.)

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Credit: Jamie McCarthy/Getty
Ashlee Simpson Parties with Boyfriend Evan Ross's Family | Ashlee Simpson

Caught in the Act

Ashlee Simpson Parties with Boyfriend Evan Ross's Family

Originally posted 08/05/2013 08:00PM

Family approval? Check!

Ashlee Simpson joined boyfriend Evan Ross at his mother Diana Ross's Los Angeles concert after-party at Hollywood hotspot Aventine Trattoria, where the new couple was spotted "dancing and kissing" throughout the night.

"She was nice and said hello to Diana," says a source. "Everyone was in a good mood and Ashlee just blended in as Diana's son's girlfriend."

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