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Ashlee Simpson & Ryan Cabrera: How Their Romance Began
27 Aug
Summary
- Ryan Cabrera had a crush on Ashlee Simpson before dating began.
- They met when Joe Simpson helped Cabrera move to Los Angeles.
- Their relationship was documented on The Ashlee Simpson Show.

Ryan Cabrera admitted to having a crush on Ashlee Simpson long before they officially started dating in 2004. He recalled being a neighbor and playing songs for her, feeling jealous of her other boyfriends.
Their romance progressed after they shared a kiss for Cabrera's "On the Way Down" music video. This led to them becoming a couple, with their relationship's early stages famously documented on "The Ashlee Simpson Show."
The couple, who met when Ashlee's father helped Cabrera move to Los Angeles, separated in 2005 after several months of dating.
Both have since moved on and found new partners. Simpson is married to Evan Ross, and they have two children. Cabrera married Alexa Bliss in 2022, and they have one child.
Despite their past romance, Cabrera and Simpson have remained good friends, with Cabrera noting that they all support each other's happiness and success.