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Ryan Cabrera, the 43-year-old hitmaker of “On the Way Down,” recently shared in an exclusive interview with People that he maintains a friendly relationship with his ex, Ashlee Simpson Ross. The pair, who famously dated back in 2004 and even appeared together on The Ashlee Simpson Show, have continued to stay amicable over the years. Cabrera revealed that not only is he on good terms with Simpson Ross but that his current wife, Alexa Bliss, also holds a fondness for her.


Despite their romantic past, Cabrera and Simpson Ross have managed to forge a healthy friendship, with the singer noting that he and Simpson Ross’s husband, Evan Ross, have been friends for quite some time. He mentioned that their connection goes beyond just the two of them, as he remains friends with Simpson Ross’s mother, Tina Ann Simpson, who even sends gifts to their daughter, Hendrix.
Reflecting on their shared history, Cabrera highlighted the positive aspects of their relationship, stating, “We have such a great history and nobody has anything bad to say about each other because we’re all just happy that everybody’s happy.” Their ability to support and root for each other’s successes has been a significant factor in maintaining a cordial dynamic despite their past romantic entanglement.
The bond between Cabrera, Simpson Ross, and Ross was evident when they attended his wedding to Bliss in April 2022. Cabrera described the atmosphere as fun, happy, and healthy, expressing his excitement in watching his past acquaintances thrive and succeed. He emphasised the importance of being able to cheer on individuals from one’s past and witness their growth and accomplishments.
Their history together extends back to 2004 when their relationship played out on national television through Simpson Ross’s reality show. The intertwining of their personal and professional lives was further represented by Cabrera’s appearance in the music video for his hit single “On the Way Down.” Despite their eventual breakup, Simpson Ross maintained a positive view of Cabrera, referring to him as a “great guy.”
Both Simpson Ross and Cabrera have moved on to new chapters in their lives. Simpson Ross was previously married to Pete Wentz from 2008 to 2011 and shares a son, Bronx, with him. She later tied the knot with Ross in August 2014 and welcomed two children, Jagger and Ziggy, with him. On the other hand, Cabrera married Bliss in April 2022, and the couple now shares a 2-year-old daughter named Hendrix Rouge.
The ability of Cabrera and Simpson Ross to navigate their past and maintain a positive relationship serves as a testament to their maturity and respect for each other’s journeys. Their story is a reminder that it is possible to transition from romantic partners to friends while supporting each other’s growth and happiness. This kind of amicable dynamic sets an inspiring example for individuals navigating past relationships and showcases the beauty of evolving relationships.
In a world where celebrity breakups often garner more attention than friendship post-breakup, the story of Ryan Cabrera and Ashlee Simpson Ross stands out as a refreshing and heartwarming tale. Their ability to transcend past romantic entanglements and embrace friendship demonstrates a level of maturity and respect that is commendable. As they continue to cheer each other on in their respective journeys, their story serves as a reminder of the power of positivity and support in all relationships.
