Women Who Ben Stiller Has Dated

This is a list of famous women who have dated Ben Stiller, with photos when available. If you're wondering "Who has Ben Stiller dated?" then you've come to the right place. This list features Ben Stiller's ex-girlfriends along with additional information about them, such as when they were born and what their profession is.

These women come in all shapes and sizes, but what they all have in common is that they're all women that Ben Stiller has either dated or canoodled with. It's not hard to get jealous of these women that Ben Stiller has gone out with, so try your best to contain your envy. This list answers the question, "What are the names of Ben Stiller's ex-girlfriends?" The list of Ben Stiller ex-girlfriends range from Amanda Peet to Rhea Durham.

Is Ben Stiller married? He married Christine Taylor in 2000, and while they announced their split in May 2017, by September 2019, the pair were rumored to be back together.

  • Ben Stiller and Christine Taylor were together for nearly 18 years before recently separating in 2017, but it was during quarantine that the couple was finally able to heal their relationship and move back in with each other. 

    They share children Ella Olivia (born in 2002), and Quinlin Dempsey (born in 2005). 

    Christine Joan Taylor-Stiller (born July 30, 1971) is an American actress. She is known for playing Marcia Brady in The Brady Bunch Movie and A Very Brady Sequel, as well as roles in The Wedding Singer, Zoolander, and DodgeBall: A True Underdog Story.
    • Age: 51
    • Birthplace: Allentown, Pennsylvania, USA
  • Amanda Peet
    Photo: Alberto Rodriguez / Getty Images

    Ben Stiller and Amanda Peet dated after they acted together in the 2005 play This Is How It Goes.

    Amanda Peet (born January 11, 1972) is an American actress. After studying at Columbia University, Peet began her acting career with small parts on television, and made her film debut in Animal Room (1995). Her featured role in the comedy The Whole Nine Yards (2000) brought her wider recognition, and she has since appeared in a variety of films, including Something's Gotta Give (2003), Identity (2003), Syriana (2005), The X-Files: I Want to Believe (2008), 2012 (2009), and The Way, Way Back (2013). On television, Peet has starred in Jack & Jill (1999–2001), Togetherness (2015–2016), and Brockmire (2016–present).
    • Age: 51
    • Birthplace: New York, New York, USA
  • Calista Flockhart
    Photo: Tinseltown / Shutterstock

    Ben Stiller and Calista Flockhart dated in 1999, right before Stiller met his future wife, Christine Taylor. 

    Calista Kay Flockhart (born November 11, 1964) is an American actress. She starred as the title character in the legal comedy-drama series Ally McBeal (1997–2002), Kitty Walker in the drama series Brothers & Sisters (2006–2011) and Cat Grant in the superhero drama series Supergirl (2015–2019). She has also been featured in a number of films, including the comedy film The Birdcage (1996), the romantic comedy film A Midsummer Night's Dream (1999), and the drama film Things You Can Tell Just by Looking at Her (2000). Flockhart has won a Golden Globe Award and Screen Actors Guild Award, and garnered three Emmy Award nominations. She is married to actor Harrison Ford.
    • Age: 58
    • Birthplace: Freeport, Illinois, USA
  • American model Rhea Durham dated Stiller for only a handful of months in 1998, before calling it quits. 

    Rhea Durham (born July 1, 1978) is an American model. She has appeared on the cover of several major fashion magazines, including French Vogue, Marie Claire, British and American ELLE. Rhea has also walked in the 2000 and 2001 Victoria's Secret Fashion Show. She guest-starred as herself on the 2001 Spin City episode, "The Wedding Scammer."
    • Age: 44
    • Birthplace: Lakeland, Florida, United States of America
  • Janeane Garofalo and Ben Stiller casually dated in 1990, but not much happened beyond that.

    Janeane Marie Garofalo (; born September 28, 1964) is an American actress, voice artist, stand-up comedian, and writer. Garofalo began her career as a stand-up comedian and became a cast member on The Ben Stiller Show, The Larry Sanders Show, and Saturday Night Live, then appeared in more than 50 movies, with leading or major roles in The Truth About Cats and Dogs, Wet Hot American Summer, The Matchmaker, Reality Bites, Steal This Movie!, Clay Pigeons, Sweethearts, Mystery Men, and The Independent, among numerous others. She has been a series regular on television programs such as Wet Hot American Summer: First Day of Camp, 24, and Girlfriends' Guide to Divorce.Garofalo is an outspoken ...more
    • Age: 58
    • Birthplace: Newton, New Jersey, United States of America
  • Jeanne Tripplehorn
    Photo: Morning / Red Rover Films

    Engaged from 1993 to 1996, Ben Stiller and Jeanne Tripplehorn almost made it down the aisle, but their roller coaster romance wasn't meant to last. 

    Jeanne Marie Tripplehorn (born June 10, 1963) is an American actress. She began her career in theatre, acting in several plays throughout the early 1990s, including Anton Chekov's Three Sisters on Broadway. Her film career began with the role of a police psychologist in the erotic thriller Basic Instinct (1992). Her other film roles include The Firm (1993), Waterworld (1995) and Sliding Doors (1998). On television, she starred as Barbara Henrickson on the HBO drama series Big Love (2006–11) and as Dr. Alex Blake on the CBS police drama Criminal Minds (2012–14), and she received a Primetime Emmy Award nomination for her performance as Jacqueline Kennedy Onassis in the 2009 HBO movie Grey ...more
    • Age: 59
    • Birthplace: Tulsa, Oklahoma, USA