Ashlee Simpson's Husband and Relationship History

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Updated April 16, 2024 10 items

Who is Ashlee Simpson dating? Many famous men have dated Ashlee Simpson, and this list will give you more details about these lucky dudes. Including Ashlee Simpson’s current boyfriend, past relationships, pictures together, and dating rumors, this comprehensive dating history tells you everything you need to know about Ashlee Simpson’s love life. 

This list features Ashlee Simpson’s ex-boyfriends along with additional information about them, such as when they were born and what they do professionally. These boys come in all shapes and sizes, but what they all have in common is that they're all men that Ashlee Simpson has either dated or linked up with. It's not hard to get jealous of these men that Ashlee Simpson has gone out with, so try your hardest to contain your envy.

From 2008 to 2011, Ashlee Simpson was married to Pete Wentz. She gave birth to their son, Bronx Mowgli, in November 2008. 

In 2014, Ashlee Simpson married second husband Evan Ross. The couple has a daughter together. 

This list of Ashlee Simpson’s boyfriends and rumored exes includes Vincent Piazza, Ryan Cabrera, Tyler Hoechlin, Carson Daly, and Wilmer Valderrama. 

  • Evan Ross

    In 2013, Ashlee Simpson started dating Evan Ross, Diana Ross's son. They became engaged in Janaury 2014, and married on Augst 30, 2014 at Diana Ross's estate in Connecticut. 

    They had daughter, Jagger Snow, in July 2015. They welcomed son Ziggy Blu on October 29, 2020. 

    Evan Ross, widely recognized as the son of the legendary Diana Ross, rose to fame with his acting chops in projects such as ATL, Pride, and the hit TV series, 90210. His career skyrocketed when he snagged a role in the Hunger Games franchise, playing the character of Messalla. Ross is also known for his music career, having released his debut single "Yes Me" in 2011 and continuing to work on various musical projects with his wife. Apart from his relationship with Ashlee, Evan has remained relatively low-key about any previous high-profile romances.

  • Vincent Piazza

    Vincent Piazza and Ashlee Simpson began their love story in June 2011 after reportedly meeting at an exclusive celebrity party. The couple enjoyed several high-profile outings and events together, including an appearance at the Emmys in 2011. However, after a year and four months of adorable red carpet moments and Instagram-worthy vacations, the pair decided to call it quits in November 2012, citing conflicting schedules as the reason behind their breakup.

    Vincent Piazza gained prominence with his role as gangster Lucky Luciano in the award-winning HBO series, Boardwalk Empire. He had previously made a mark in the acting world with notable performances in Rescue Me and The Sopranos. Vincent has also appeared in several films, including Jersey Boys, a 2014 musical drama directed by Clint Eastwood. Though Ashlee Simpson was his most high-profile relationship, he has since remained tight-lipped about his personal life and romantic interests.

  • Pete Wentz

    Ashlee Simpson met Pete Wentz in early 2006 at the MTV Video Music Awards, and the couple confirmed their relationship in April of that year. The pair's whirlwind romance led to an engagement in April 2008, followed by a wedding ceremony on May 17, 2008. Pete and Ashlee shared many unforgettable experiences, including the birth of their son Bronx Mowgli Wentz in November the same year. Sadly, the couple parted ways and finalized their divorce in 2011, but they remain on good terms as co-parents to their son.

    Pete Wentz rose to fame as the bassist, primary lyricist, and backup vocalist for the massively successful rock band, Fall Out Boy. With numerous chart-topping hits and a loyal fan base, Wentz has become a household name in the world of pop-punk. Additionally, Wentz has ventured into fashion, launching his clothing line Clandestine Industries, and dabbled in acting with guest appearances on shows like One Tree Hill. Before his relationship with Ashlee, Pete was linked to Michelle Trachtenberg and Jeanae White.

  • Braxton Olita

    Braxton Olita

    Ashlee Simpson and Braxton Olita's relationship bloomed in 2005, as the two met while Olita was playing guitar for Ashlee on tour. From sharing the stage and traveling around the world together, their connection grew stronger and more intimate. They often enjoyed vacations to Hawaii, which included a memorable trip in 2006 where they were photographed soaking up the sun and love. However, the couple eventually decided to part ways in July 2006, after nearly a year and a half of dating.

    Braxton Olita initially gained attention as a guitarist for Ashlee Simpson's band during her rise to fame. In addition to his musical talents, he is also recognized as a model, previously gracing the pages of magazines such as Vogue Italia. Braxton has kept a rather low profile since his relationship with Ashlee Simpson ended, making it difficult to determine any other high-profile romances or further updates on his career.

  • Wilmer Valderrama

    Wilmer Valderrama and Ashlee Simpson were rumored to have been romantically involved after they were spotted together at a nightclub in Los Angeles in 2005. While neither party ever confirmed the relationship, they were seen sharing a few cozy moments and flirtatious exchanges during that time. Despite the paparazzi's close watch, their supposed connection seemed to be short-lived, with both parties moving on rather quickly.

    Wilmer Valderrama is best known for his quirky and lovable character Fez on the hit TV series, That '70s Show. Following his successful run on the show, he went on to appear in various films, television series, and even ventured into the world of voice acting. Valderrama has also gained notoriety for his high-profile relationships, having dated stars like Mandy Moore, Lindsay Lohan, and most notably, Demi Lovato with whom he had a six-year on-and-off relationship.

  • Ryan Cabrera

    Ashlee Simpson and Ryan Cabrera first met in the early 2000s and struck up a close friendship. Their relationship took a romantic turn in 2004 after Cabrera moved into Simpson's home to work on his debut album. The couple appeared smitten with each other during their time together, and Cabrera even made a few appearances on Ashlee's reality show, The Ashlee Simpson Show. Unfortunately, their romance fizzled out after just a few months, and they returned to being good friends.

    Ryan Cabrera launched his music career with the hit single "On the Way Down" in 2004. His debut album, Take It All Away, went on to achieve Platinum status and solidified his spot in the early 2000s pop-rock scene. Cabrera has continued making music and touring over the years, albeit with less commercial success. Apart from his relationship with Ashlee Simpson, he has been linked to other high-profile stars, including Avril Lavigne and Audrina Patridge.

  • Tyler Hoechlin

    The nature of Ashlee Simpson and Tyler Hoechlin's alleged romance is shrouded in mystery. Rumors of a possible connection began swirling in 2004, but the relationship was never officially confirmed by either party. Despite the speculative nature of their coupling, it is clear that whatever may have happened between them was short-lived and remained mostly under wraps.

    Tyler Hoechlin rose to fame with his portrayal of Michael Sullivan Jr., in the 2002 film Road to Perdition. His acting career took off further with his role as Derek Hale in the popular MTV series, Teen Wolf. Today, Hoechlin is widely recognized for his role as Superman in The CW's Supergirl and other related series. Though his rumored relationship with Ashlee Simpson remains one of his more high-profile connections, Hoechlin has kept his romantic life relatively private.

  • Gregory Smith

    Gregory Smith and Ashlee Simpson were briefly linked in 2003 when they were spotted on a few casual outings together. Although a romantic connection was never explicitly confirmed, the two were said to have met at a Hollywood party and enjoyed spending time together. The nature of their relationship remains elusive, as neither party ever commented on the situation.

    Gregory Smith rose to fame for his portrayal of Ephram Brown on the critically acclaimed TV series, Everwood. He has since appeared in several films and television series, most notably as Dov Epstein in the Canadian police drama, Rookie Blue. Currently, Smith is focusing on his career as a director, having directed episodes of popular TV shows such as Arrow, Supergirl, and Riverdale. Regarding high-profile relationships, Smith has been linked to model-turned-actress Taylor McKay, whom he married in 2019.

  • Carson Daly

    Carson Daly and Ashlee Simpson were a rumored item back in 2003, with whispers of their connection circulating after they were spotted together on multiple occasions. However, neither party confirmed the relationship, nor did they provide any substantial evidence that they were, in fact, an item. This potential romance was short-lived and remains a mystery to this day.

    Carson Daly is a television and radio personality best known for his work as the host of Last Call with Carson Daly and The Voice. He started his career as a VJ for MTV, hosting the popular show Total Request Live (TRL). Alongside his television work, Daly has also made a significant impact in radio, hosting his morning show on Los Angeles-based radio station KAMP-FM. In terms of high-profile relationships, Carson has been linked to stars like Jennifer Love Hewitt and Tara Reid, and is now happily married to Siri Pinter, a food blogger, and producer.

  • Josh Henderson

    Ashlee Simpson and Josh Henderson's relationship began and ended in 2002, making it one of her earliest high-profile romances. The couple reportedly met through mutual friends and enjoyed a few months of dating before ultimately parting ways. To this day, the exact details of their relationship remain largely scarce and unexplored.

    Josh Henderson first gained recognition as a contestant on the WB talent competition show, Popstars. Although his music career was short-lived, he transitioned to acting and found success with roles on popular television shows like Desperate Housewives and the reboot of Dallas. More recently, he appeared in the E! network's series, The Arrangement. While his relationship with Ashlee Simpson remains one of his more high-profile romances, Henderson has also been linked to stars such as Paris Hilton and Audrina Patridge.