Where Ryan Cabrera, Ashlee Simpson Stand 20 Years After Breakup

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Ryan Cabrera and Ashlee Simpson Ross’ relationship did not take a dive.

The singer of “On the Way Down,” who dated Ashlee Simpson in 2004 before they broke up in 2005, says they remain connected.

I recently chatted with Ryan, and he shared something really sweet! He confirmed they’re good friends with Alexa Bliss – in fact, his wife absolutely adores her. It’s so lovely to see these positive connections!

He added that he still visits Hendrix’s grandmother at the showroom, and they always have gifts for their daughter. He said everyone is very supportive of each other.

Ryan married WWE star Alexa in 2022, and they have a 2-year-old son named Hendrix. Ashlee has been married to Evan Ross since 2014, and they share two children: a 10-year-old son named Jagger and a 5-year-old son named Ziggy. Ashlee also has a 17-year-old son named Bronx from a previous relationship with Pete Wentz.

Even though Ryan and Ashlee have both moved on with their lives, Ryan shared that Ashlee and her husband, Evan, have continued to be supportive – they even came to his wedding to Alexa.

You know, looking back, what I cherish most is the genuinely positive vibe we all share. It’s amazing – there’s no drama, just a collective happiness that everyone is doing well. Seeing everyone build beautiful families and thrive is incredibly rewarding, and honestly, it fills my heart with joy. It’s just wonderful to witness that kind of growth and happiness around you.

Ryan described it as a really positive and supportive place. He also said it’s great to reconnect with old friends and celebrate their successes.

Ashlee received a lot of support when she returned to performing earlier this year with her Las Vegas show. It was a special occasion, as it also celebrated her 11th wedding anniversary with her husband.

She explained to TopMob News in September that it was special because Evan had never watched her perform. While they’ve performed together before, he hadn’t ever seen her on stage.

She recounted him saying, “You’re amazing!” and shared that it genuinely moved her, calling it the kindest thing anyone had ever done.

For more stars who have no bad blood and are friendly with their exes, keep reading…

They are definitely not getting back together. However, with all the recent interactions – birthday celebrations, affectionate hugs, and even playfully acting out a romantic scene during the virtual reading of Fast Times at Ridgemont High – it feels like they’re just teasing everyone who hoped they’d reconcile.

It takes a certain level of confidence to playfully tease your ex on his own show. That’s exactly what Sarah did when she appeared on Jimmy Kimmel’s talk show to promote her series, I Love You, America, and jokingly commented on his wife, Molly Kimmel. She quipped, “It’s not fair! She’s got the updated, more aware Jimmy. I only had the ‘Man Show’ version of Jimmy.”

 

Honestly, some people seemed more upset about this relationship ending than the people involved! When Anna—who is now married to Michael Barrett—found out Chris Pratt was going to marry Katherine Schwarzenegger in 2019, she actually volunteered to perform the wedding ceremony. She even sent a gift when their daughter, Lyla, was born in August 2020. Everyone was happy for Anna’s son, Jack, to have a little sister, and a source said Anna was genuinely supportive of the new family.

As a lifestyle expert, I’ve seen plenty of couples struggle after a breakup, but honestly, I’m really impressed with how things have turned out for these HGTV stars. Despite a difficult split over four years ago, they’re absolutely thriving! They’re successfully co-parenting their adorable kids, Taylor and Brayden, and they’re still knocking it out of the park with their home renovation projects, turning fixer-uppers into dream homes for others. It just goes to show what can happen when you prioritize what really matters.

Lenny Kravitz and Lisa Bonet, parents to actress Zoe Kravitz, describe their relationship as a close, familial bond – what Lenny called being “best friends” in a 2013 interview with Oprah Winfrey. Despite their divorce, they maintain a happy connection. Lenny spoke fondly of his ex-wife, who later married and then divorced Jason Momoa, saying their continued closeness is a positive example of what’s possible.

Since the Dancing With the Stars co-host and retired hockey player ended their relationship in 2020, they’ve consistently shown they remain friendly with each other.

When Brooks announced he was getting engaged to Katrín Tanja Davíðsdóttir in December 2024, Julianne shared her excitement on Instagram. She wrote a message wishing them both a lifetime of happiness, fun, and adventures as they start this new chapter together.

The dancer, her ex-husband, and his pregnant fiancée all spent a day together at the lake. She shared a photo of the four of them, calling them “three cuties” and describing it as a special day.

Since splitting up in 2015, the parents of Violet, Seraphina, and Samuel have successfully co-parented. They’ve continued to share vacations and holidays, and Ben has publicly praised his ex-partner, calling her “an amazing mother” in a 2016 interview with TopMob News.

Nina and Ian broke up in 2013 after dating for three years, but they stayed friends. The following year, Nina began dating Nikki Reed and they quickly got married. As a result, Nina became friends with Nikki, who is known for her role in the Twilight films.

The couple broke up in July 2016 after being together for five years. The singer later shared on Howard Stern’s radio show in October that she remained very close to her ex, describing him as both a former lover and a long-time friend.

“We love each other,” she said. “That’s it.”

Even years after The Office ended in 2013, the chemistry between its stars remained obvious, and Mindy Kaling understands why fans still root for them as a couple. In a 2019 interview with Good Housekeeping, she admitted that if she were a viewer, she’d feel the same way. However, she explained that B.J. Novak has become more like family than just a friend, which is why she chose him to be a godparent to her children.

After their divorce was finalized in 2011, the former couple easily continued to raise their son, Bronx. The Fall Out Boy singer has praised his ex-wife, calling her a fantastic mother.

It sounds like she’s moved on from her past relationship! The musician, formerly known as one of the JoBros, has stated he and his ex are still on good terms, describing their connection as simply friendly. He says they maintain a positive relationship.

Jennifer and her Dexter co-star first became acquainted on the set of the show in 2006, and their relationship turned romantic two years later. Despite divorcing in 2011, Jennifer later confirmed they remained on good terms, with ‘nothing but love and respect’ for each other.

Bruce Willis and Demi Moore are famously friendly exes, and their daughters – Rumer, Tallulah, and Scout – have helped them maintain that bond. So, it wasn’t surprising when they decided to spend the COVID-19 lockdown together in Idaho. Sounds like they even had some fun, maybe with a dance party!

Four years after her 2014 divorce, Jennifer Lopez still spoke highly of her ex-husband, Marc Anthony, the father of her twins, Max and Emme. In a 2018 interview on Sunday Today, she shared that Marc had been instrumental in boosting her confidence. He consistently affirmed her talent, telling her she was a fantastic singer and encouraging her not to listen to anyone who said otherwise. Lopez expressed deep respect for him, considering him one of the greatest singers ever.

Despite facing personal challenges, the actress remains supportive of her ex-husband and former Scream colleague. Eight years after their 2010 divorce, she described it as a relatively amicable split while appearing on Running Wild With Bear Grylls. She also emphasized their successful co-parenting relationship with their daughter, Coco.

Although their relationship ended in 2007, they still had great chemistry on screen when they starred together in the 2011 film Bad Teacher.

Although their 2013 separation was difficult at first, the actors are now able to vacation together as a group. Speaking to LaPalme Magazine, the Twilight star shared that he enjoys a good relationship with his ex-wife’s husband, and highlighted a 2017 trip to Cancun where they were joined by Garth, Dave Abrams, Peter’s fiancée Lily Anne Harrison, and their three daughters, Luca, Lola, and Fiona. He also spoke about his ongoing connection with Jennie, explaining, “People enter your life for a reason, and relationships evolve. Just because you’re not together doesn’t mean you can’t still care for each other.”

Even though they unexpectedly separated in September 2012, the couple worked to appear supportive of each other for the sake of their children. In a 2014 interview with Howard Stern, she explained that she and Will remained very close friends and were successfully co-parenting. She didn’t view their ten-year marriage as a failure, believing that all relationships face challenges.

The Grammy-winning artist and her ex-husband, who officially divorced in January 2024, have maintained a friendly relationship while raising their son, Hayes. They even live only five minutes away from each other, making it easy to co-parent.

“Our stops are really easy,” Maren told The Zoe Report in May 2025, “and we’ll have family dinners.”

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2025-12-18 16:48