Ryan Cabrera is sharing an update on where he currently stands with ex-girlfriend Ashlee Simpson.
If you forgot, the 43-year-old “On the Way Down” singer and 41-year-old “Pieces of Me” singer dated back in 2004 and he even appeared on her MTV reality show The Ashlee Simpson Show.
In a new interview, Ryan revealed that more than two decades after they dated, he and Ashlee are still on good terms.
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Ryan Cabrera is singing his praises for ex-girlfriend Ashlee Simpson!
If you forgot, Ryan, 43, and Ashlee, 41, dated back in 2004 and their romance was documented in MTV’s The Ashlee Simpson Show.
In a new interview, Ryan reacted to Ashlee‘s new music chapter and her Las Vegas residency.
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Jessica Simpson is opening up about her long-awaited return to music!
The 45-year-old singer and fashion designer dropped two EPs this year, Nashville Canyon parts one and two, marking her first original releases since her album Do You Know in 2008.
During an appearance on The Jennifer Hudson Show, which aired Thursday (October 2), Jessica talked about her comeback, as well as possibly releasing music with younger sister Ashlee Simpson.
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Isabela Ferrer is heading back into the public eye after becoming part of the It Ends With Us legal battle between Blake Lively and Justin Baldoni.
The 24-year-old actress, who played the younger version of Blake in the movie, stepped out on Saturday (September 13) for the alice + olivia by Stacey Bendet Spring 2026 Presentation at Surrogate’s Court in New York City.
The New York Fashion Week event was attended by a star-studded crowd.
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Ciara and Tyla shared a fierce moment inside the Pandora Celebrates Talisman Collection Launch event held at The Halo on Monday (September 8) in New York City.
The two singers were among several celebrities at the jewelry launch to celebrate the iconic brand’s new collection, which is on sale now.
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Ashlee Simpson and Evan Ross are hitting the red carpet!
The married couple posed for photos together as they arrived at the 2025 MTV Video Music Awards on Sunday (September 7) at UBS Arena in Elmont, New York.
For the big event, the 40-year-old “Pieces of Me” singer wore a shimmering black dress while the 37-year-old actor/singer coordinated in a black suit.
During the show, Ashlee is set to hit the stage to present.
The 2025 VMAs show is airing live on CBS for the first time with LL Cool J returning to host after co-hosting in 2022. Lady Gaga leads the list of nominations this year with 12 nods and she’s part of the star-studded lineup of performers who will appear during the show. Make sure to tune in at 8pm ET/5pm PT for the live show.
Click through the gallery inside for 20+ pictures of Ashlee Simpson and Evan Ross arriving at the event…
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Ashlee Simpson only has one regret about The Ashlee Simpson Show.
The 40-year-old “L.O.V.E.” singer spoke out in a recent episode of Pod Meets World, and revealed that her kids have started to watch her old MTV reality TV show, which aired for two seasons starting in 2004.
The classic ’00s reality TV show chronicled her life as a musician on her first major tour, and living in the shadow of sister Jessica Simpson‘s fame.
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