25 Actors Who’ve Played Love Interests More Than Once

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Love is in the air…or at least on the screen!

1.

Kate Winslet and Leonardo DiCaprio


20thCentFox/Courtesy Everett Collection / DreamWorks/Courtesy Everett Collection

Love interests in: Titanic (1997) and Revolutionary Road (2008)

The undeniable chemistry between Leonardo DiCaprio and Kate Winslet as Jack and Rose in Titanic broke records at the box office. It’s no surprise they played a married couple almost a decade later in the romantic drama Revolutionary Road.

2.

Tom Hanks and Meg Ryan


Warner Bros/Courtesy Everett Collection / TriStar Pictures/Courtesy Everett Collection

Love interests in: Joe Versus the Volcano (1990), Sleepless in Seattle (1993), You’ve Got Mail (1998), and Ithaca (2015)

This iconic rom-com pair has worked together for over two decades. Meg Ryan revealed why she loves working with Tom Hanks in an interview with Sleepless in Seattle producer Gary Foster, “He’s just so easy. He listens; he roots for other people.”

3.

Emma Stone and Ryan Gosling


Warner Brothers/Courtesy Everett Collection / Summit Entertainment / courtesy Everett Collection

Love interests in: Crazy, Stupid, Love (2011); Gangster Squad (2013); La La Land (2016)

Emma Stone and Ryan Gosling have worked together so much over the years that they consider each other real friends. During a Q&A at the 45th annual Telluride Film Festival, Stone noted, “I can’t even imagine what my life would be without Ryan.”

4.

Julia Roberts and Richard Gere


Buena Vista Pictures Courtesy Everett Collection / Paramount Pictures Courtesy Everett Collection

Love interests in: Pretty Woman (1990) and Runaway Bride (1999)

Richard Gere wasn’t originally fully on board with playing Edward Lewis in Garry Marshall’s Pretty Woman. Thankfully, Roberts and Marshall flew to New York to meet with Gere and convince him otherwise. Roberts told SiriusXM, “He changed all of our lives forever by agreeing to do this movie.” Nine years later, Gere and Roberts played lovers in Marshall’s Runaway Bride.

5.

Bradley Cooper and Jennifer Lawrence


Weinstein Company / courtesy Everett Collection / Magnolia Pictures/Courtesy Everett Collection

Love interests in: Silver Linings Playbook (2013) and Serena (2014)

Outside of playing love interests in Silver Linings and Serena, Lawrence and Cooper have also appeared together in American Hustle (2013) and Joy (2015). When asked if he was potentially dating Lawrence off camera, Cooper told Entertainment Tonight, “I could be her father.”

6.

Adam Sandler and Drew Barrymore


New Line / courtesy Everett Collection / Columbia / courtesy Everett Collection Warner Bros. Pictures / courtesy Everett Collection

Love interests in: The Wedding Singer (1998), 50 First Dates (2004), and Blended (2014)

To this day, Adam Sandler credits Drew Barrymore for getting continuously cast as a romantic lead. Sandler told Howard Stern, “Drew liking me made it seem like girls were allowed to like me in movies.”

7.

Jennifer Lopez and Ben Affleck


Columbia / courtesy Everett Collection / Miramax / courtesy Everett Collection

Love interests in: Gigli (2003) and Jersey Girl (2004)

Jennifer Lopez and Ben Affleck met on the set of Gigli, a story of trained assassins, kidnappings, crime bosses, and most of all, love. And while it tanked at the box office, we have Gigli to thank for “Bennifer.” The pair bounced back when J.Lo played Ben’s wife who died during labor in Jersey Girl.

8.

Anne Hathaway and Jake Gyllenhaal


Focus Films/Everett Collection / Twentieth Century Fox Film Corporation/Courtesy Everett Collection

Love interests in: Brokeback Mountain (2005) and Love & Other Drugs (2010)

Technically, Jake Gyllenhaal’s love interest in Brokeback Mountain was the late Heath Ledger. However, Anne Hathaway played his girlfriend turned wife and that has to count for something…right? Regardless, their onscreen connection was extremely evident in Love & Other Drugs, a love story between a pharmaceutical salesman and a free-spirited woman suffering from Parkinson’s disease.

9.

Eugene Levy and Catherine O’Hara


Warner Brothers / courtesy Everett Collection / CBC / courtesy Everett Collection

Love interests in: Best in Show (2000), A Mighty Wind (2003), and Schitt’s Creek (2015)

Eugene Levy and Catherine O’Hara met in the ’70s performing for the Toronto branch of the Second City improv theater. Since then, this Canadian team has captured laughs, hearts, and multiple Emmy Awards together.

10.

Matthew McConaughey and Kate Hudson


Paramount / courtesy Everett Collection / Warner Bros. / courtesy Everett Collection

Love interests in: How to Lose a Guy in 10 Days (2003) and Fool’s Gold (2008)

Matthew McConaughey believes that in order for a romantic comedy to work, the actors have to have a certain level of chemistry. Thankfully, he felt that chemistry with Kate Hudson in How to Lose a Guy in 10 Days, “We had a really good push and pull,” he stated in a video posted on his Twitter. “She had a lot of rock ‘n’ roll and I did too, the way we would parry with each other really worked in that film.” In fact, it worked so well that the duo paired up again for the treasure hunting rom-com Fool’s Gold.

11.

Sandra Bullock and Keanu Reeves


20th Century Fox Film Corp Courtesy: Everett Collection / Warner Bros./courtesy Everett

Love interests in: Speed (1994) and The Lake House (2006)

Keanu Reeves and Sandra Bullock weren’t just interested in each other on the big screen. The actors both disclosed having crushes on each other while filming Speed during interviews on the Ellen DeGeneres Show.

12.

Jon Hamm and Kristen Wiig


Universal Pictures/ Lionsgate/Courtesy Everett Collection

Love interests in: Bridesmaids (2011) and Friends with Kids (2011)

From that awkward opening sex scene in Bridesmaids to playing a couple going through a divorce in Friends with Kids, Jon Hamm and Kristen Wiig have proved they have range as a duo. “I mean, I’ve worked with Jon a lot and most of it has been comedic stuff,” Wiig said in an interview with HitFix. “It was an honor for me to do dramatic scenes with him and it was very comfortable.”

13.

Owen Wilson and Rachel McAdams


New Line / courtesy Everett Collection / Sony Pictures Classics / courtesy Everett Collection

Love interests in: Wedding Crashers (2005) and Midnight in Paris (2011)

Audiences watched Owen Wilson and Rachel McAdams fall in love in Wedding Crashers and fall out of love in Midnight in Paris. Regardless of the drastically different tones of these two films, McAdams and Wilson make for an adorable, albeit dysfunctional, couple!

14.

Reese Witherspoon and Paul Rudd


New Line Cinema / courtesy Everett Collection / Columbia Pictures / courtesy Everett Collection

Love interests in: Overnight Delivery (1998) and How Do You Know (2010)

Paul Rudd and Reese Witherspoon go way back! So far back that Reese recently shared a selfie of her and Paul from 1996 on her Instagram. And while Overnight Delivery and How Do You Know were filmed over a decade apart, these two Hollywood icons seemingly just don’t age.

15.

Goldie Hawn and Kurt Russell


Warner Bros. / courtesy Everett Collection / MGM / courtesy Everett Collection / Netflix / Courtesy Everett Collection

Love interests in: Swing Shift (1984), Overboard (1987), The Christmas Chronicles (2018), and The Christmas Chronicles 2 (2020)

The chemistry between Goldie Hawn and Kurt Russell is probably so fantastic because they’ve been together in real life for over three decades.

16.

Adam Sandler and Jennifer Aniston


Columbia Pictures / courtesy Everett Collection / Netflix / courtesy Everett Collection

Love interests in: Just Go with It (2011) and Murder Mystery (2019)

Aside from starring in two romantic comedies together, this pair considers each other family. Aniston and Sandler met at a deli back in the ’90s. Jennifer told Jimmy Kimmel, “We were friends before Friends.”

17.

Brad Pitt and Cate Blanchett


Paramount Classics / courtesy Everett Collection / Paramount/Courtesy Everett Collection

Love interests in: Babel (2006) and The Curious Case of Benjamin Button (2008)

Capturing a love story as complicated as Benjamin Button’s and Daisy Fuller’s can’t be easy. Thankfully, Brad Pitt and Cate Blanchett had practice from working together on Babel in 2006.

18.

Jason Segel and Emily Blunt


Twentieth Century Fox Film Corporation/Courtesy Everett Collection / Universal Pictures / courtesy Everett Collection

Love interests in: Gulliver’s Travels (2010) and The Five-Year Engagement (2012)

Emily Blunt and Jason Segel make an adorkable onscreen couple. This video of Segel and Emily Blunt’s husband, John Krasinski, performing karaoke at a dive bar in Ann Arbor, where The Five-Year Engagement was filmed, proves they get along even when the cameras stop rolling.

19.

Tom Hanks and Julia Roberts


Universal / courtesy Everett Collection

Love interests in: Charlie Wilson’s War (2007) and Larry Crowne (2011)

Sparks flew between Tom Hanks and Julia Roberts as a Texas congressman and socialite in the critically acclaimed Aaron Sorkin drama Charlie Wilson’s War. They ditched their fancy titles to play a professor and student in Larry Crowne, but the chemistry between these two remained strong!

20.

Dax Shepard and Kristen Bell


Open Road Films/Courtesy Everett Collection /  Warner Bros. /Courtesy Everett Collection

Love interests in: Hit & Run (2012) and CHiPs (2017)

Kristen Bell and Dax Shepard are easily one of Hollywood’s most beloved couples. It’s no surprise their connection shines even when playing fictional characters!

21.

Keanu Reeves and Winona Ryder


Columbia Pictures / courtesy Everett Collection / Warner Independent/Everett Collection / Regatta /Courtesy Everett Collection

Love interests in: Bram Stoker’s Dracula (1992), A Scanner Darkly (2006), and Destination Wedding (2018)

Keanu Reeves and Winona Ryder first worked together on the set of Bram Stoker’s Dracula in 1992. Ryder revealed to Entertainment Weekly that she and Reeves might actually be married in real life. Francis Ford Coppola used a real Romanian priest to wed the couple in the film, “We shot the master and he did the whole thing. So I think we’re married.”

22.

Christian Bale and Amy Adams


Columbia Pictures / courtesy Everett Collection / Annapurna Pictures /Courtesy Everett Collection

Love interests in: American Hustle (2013) and Vice (2018)

This pair must love working together, because in addition to playing couples in American Hustle and Vice, they worked together in 2010 on The Fighter. When Adams and Bale team up, it’s basically a guarantee that Oscar nominations will follow.

23.

Antonio Banderas and Salma Hayek


Sony Pictures/Courtesy Everett Collection / Paramount Pictures/Courtesy Everett Collection

Love interests in: Desperado (1995) and Puss in Boots (2011)

Antonio Banderas once bought Salma Hayek two monkeys for her birthday that were originally supposed to appear in Desperado, but they were cut from the film. She treasured the gift and the pair worked together again providing the voices for Kitty Softpaws and the titular Puss in Boots.

24.

Julia Roberts and Clive Owen


Columbia / courtesy Everett Collection / Universal / courtesy Everett Collection

Love interests in: Closer (2004) and Duplicity (2009)

After working together in Closer, Julia Roberts and Clive Owen teamed up for the romantic spy comedy Duplicity. Roberts told Parade’s Jeanne Wolf they laughed through all the film’s steamy scenes. “We were like having two pet raccoons.”

25.

And finally, Kristen Stewart and Jesse Eisenberg


Miramax / courtesy Everett Collection / Lionsgate / courtesy Everett Collection

Love interests in: Adventureland (2009), American Ultra (2015), and Café Society (2016)

Kristen Stewart and Jesse Eisenberg have a fascinating energy between them that keeps audiences engaged time and time again. “I think we’re both just kind of weirdos,” Stewart said on the Today Show about working with Eisenberg. “As a team, we’re a little bit less weird, because we get it from each other.”

If we missed any electric pairs, let us know in the comments!

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