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Ashlee Simpson Loves and Hookups

Updated November 2, 2020 10.4k views10 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. 

  • Photo: Michael Tran / Getty Images

    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. 

    • Age: 33
    • Birthplace: Greenwich, Connecticut, USA
  • Photo: Jeff Kravitz / Getty Images

    Vincent Piazza and Ashlee Simpson dated from June 2011 to November 2012.

    Vincent Piazza (born May 25, 1976) is an American film, television and stage actor. He is best known for his portrayal of gangster Lucky Luciano in the HBO television series Boardwalk Empire. He has also played Earl Hefner in the comedy-drama Rocket Science (2007) and singer Tommy DeVito in Clint Eastwood's film adaptation of Jersey Boys (2014)....  more
    • Age: 45
    • Birthplace: Middle Village, New York City, New York, USA
  • Photo: Jeff Schear / Getty Images

    In 2006, Ashlee Simpson started dating Fall Out Boy bassist Pete Wentz. They became engaged in April 2008, and married on May 17, 2008 with her father officiating the ceremony. 

    The couple had their first child together, son Bronx Mowgli, in November 2008. They later divorced in 2011. 

    • Age: 42
    • Birthplace: Wilmette, Illinois, USA

    #8 of 55 Straight Edge Celebrities#232 of 262 The Greatest Male Celebrity Role Models#21 of 97 Which Celeb Do You Want as Your Introverted Best Friend?

  • Photo: Chris Polk / Getty Images

    Braxton Olita

    Ashlee Simpson dated her band's guitarist Braxton Olita from October 2005 to July 2006.

    Braxton Olita is an American musician and vocalist. Born in Honolulu, Hawaii, Olita has worked with artist Ashlee Simpson, rock band Thirty Seconds to Mars, and more recently has joined music group U.G.L.Y., signed to Chris Brown's recording label CBE....  more
    • Age: 36
    • Birthplace: Honolulu, Hawaii