Watch: Celeb Couples You Forgot DatedLove hurts. Love scars. Love wounds and marks. It's just that sometimes it fails to leave that particular impression on our collective consciousness. Because while we could confidently recite every last Kardashian-Jenner ex from memory, even we forgot about that mid-aughts stretch when Natalie Portman was potentially leaving her scarf at Jake Gyllenhaal's sister's house. And we were definitely, uh, colorblind to the fact that Reese Witherspoon dated this heartthrob before falling hard for future husband Ryan Phillippe on the set of 1999's Cruel Intentions. (You could even say we were taffy stuck and tongue tied.) Plus there's the fact that Vanderpump Rules star Katie Maloney was almost enjoying the best days of her life with Crispin Glover after a chance encounter with the actor at the Sundance Film Festival near her Utah hometown. Following a screening of his 2005 directorial debut What Is It? ("It was the weirdest movie I've ever seen," the reality star confessed), the pair enjoyed some tea, both of the literal and metaphorical variety. "He's really nice and kind and was asking questions about my life and my family," Maloney recalled. "I grew up in Park City, so we were talking about that."photosCelebrity Couples Who Found Love on SetAnd since Valentine's Day provides us all an opportunity to celebrate love of all kinds, this Feb. 14 we're raising our glasses high and toasting both to Hollywood's current power couples and those that could have been rocking the red carpet for years to come. Admittedly, we can't really imagine a world in which Blake Lively and Ryan Reynolds aren't end game, but it's still fun to look back at the stars the Deadpool actor was kicking it with before the pals fell hard for one another and wed in 2012. Check out everyone you forgot that he-and other stars-dated. Jim Smeal/Ron Galella Collection via Getty ImagesBrad Pitt and Juliette LewisThey played doomed lovers twice, in 1990's Too Young to Die? and 1993's Kalifornia, but in real life they had a perfectly lovely relationship. "I still love the woman," Pitt, who was Lewis' date to the 1992 Oscars when she scored a Supporting Actress nomination for Cape Fear, told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her...
It was one of the greatest relationships I've ever been in. The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"Jim Smeal/WireImageWinona Ryder and Matt DamonIt wasn't just a Gen X fever dream, they really closed out the 20th century as a couple after, legend has it, being introduced by Gwyneth Paltrow (who famously dated Damon's best bud Ben Affleck). They split up in 2000. After the fact, Damon called Ryder a "great woman" in a 2004 Playboy interview, while Ryder told Black Book in 2009, "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him."Jason Kempin/Getty ImagesCameron Diaz and Justin TimberlakeThere was something about their chemistry at the 2003 Nickelodeon Kids' Choice Awards, where Diaz presented Timberlake with the award for Best Burp-because they dated for almost four years, seriously enough to issue a statement when their relationship ended in 2007, "mutually and as friends, with continued love and respect for one another."Tom Kingston/WireImageAlec Baldwin and Kristin DavisThe most exciting, challenging and significant relationship of all is the one you have with yourself, but Sex and the City alum Kristin Davis still had a good time dating Alec Baldwin when she was starring on the HBO series. Referencing an old flame who ended things after she loaned him $5,000, Kristin made it clear on a February 2025 episode of the Literally! With Rob Lowe podcast that the mystery man was definitively not the three-time Emmy winner. "Alec Baldwin was so rich by the time I dated Alec Baldwin," Kristin shared. "I would have never needed to lend Alec $5,000. Oh my God."Kevin Winter/Getty ImagesDavid Moscow and Kerry WashingtonThe Scandal star appeared on the cover of InStyle Weddings in 2005 when she was engaged to the Big actor, but they split up in 2007.
Patrick McMullan/Patrick McMullan via Getty ImagesMadonna and Tupac ShakurMadonna never addressed the story that she dated the rapper, who was killed in 1996 when he was only 25, until 2015. When Howard Stern brought up her infamously feisty 1994 chat with David Letterman, she explained, "I was dating Tupac at the time, and the thing is...he got me all riled up on life in general."Tim Mosenfelder/Corbis via Getty ImagesJake Gyllenhaal and Reese WitherspoonAfter her divorce from Ryan Phillippe and before marrying agent Jim Toth, Reese starred with Jake in the 2007 thriller Rendition and they dated for a couple of years. "She is, as I would say about most of the women who I'm close friends with or had relationships in my life," Jake said admiringly of his ex, "one of the smartest, strongest people I've ever met."I