Actors Who Have Played Couples More Than Once Movie Couples: Stars Who've Paired Up Multiple Times by Shannon Vestal 11/2/14 121 Reactions 0 Shares Print 0 0 0 0 0 Valentine's Day has us thinking about our favorite romantic movies — and our favorite onscreen couples. There are many actors in Hollywood who have great chemistry, and there are a certain number of couples whose first onscreen romance was so nice, they did it twice (or more!). Click through to see who just can't stop romancing each other on screen. Start Tom Hanks and Meg Ryan What’s Your Reaction? 0 0 0 0 0 0 Tom Hanks and Meg Ryan actually appear in three different movies as love interests; 1990's Joe Versus the Volcano and 1998's You've Got Mail bookend their onscreen love affair (Sleepless in Seattle is the third). We'd be happy to see them reunited for one more movie, because each of their love stories charms us every single time we watch. Source: Warner Bros. 1 / 23 Leonardo DiCaprio and Kate Winslet What’s Your Reaction? 0 0 0 0 0 0 The fact that star-crossed lovers Jack and Rose are separated by death in Titanic is one of film's big tragedies, and it seemed right that DiCaprio and Winslet got a second chance to be together 11 years later in Revolutionary Road — until we saw how depressing Revolutionary Road is. Can't these two just have a happy ending?! Source: Paramount Pictures, Disney 2 / 23 Channing Tatum and Jenna Dewan What’s Your Reaction? 0 0 0 0 0 0 This real-life married couple met on the set of 2006's Step Up, but their onscreen collaborations didn't stop there. After they got married, they played boyfriend and girlfriend in 2012's reunion drama 10 Years. Source: Anchor Bay Entertainment Source: Disney 3 / 23 Matthew McConaughey and Kate Hudson What’s Your Reaction? 0 0 0 0 0 0 These bubbly actors seem like they have so much fun together on screen, first in How to Lose a Guy in 10 Days, then in Fool's Gold, which followed five years later. Maybe it's the fact that their characters are always a little bit contentious . . . but ultimately want to make out. Source: Paramount Pictures, Warner Bros. 4 / 23 Richard Gere and Julia Roberts What’s Your Reaction? 0 0 0 0 0 0 In 1990's Pretty Woman, Richard Gere rescues Julia Roberts's character from a life of prostitution, and then, he had to save her again in Runaway Bride nine years later — from her commitment issues. Source: Paramount Pictures, Disney 6 / 23 Anne Hathaway and Jake Gyllenhaal What’s Your Reaction? 0 0 0 0 0 0 Their love story isn't so sweet in Brokeback Mountain — he's gay, after all, and in love with someone else. But in Love and Other Drugs, Anne Hathaway and Jake Gyllenhaal have a much more romantic love story (and better hair). Source: Focus Features, 20th Century Fox 6 / 23 Emma Stone and Ryan Gosling What’s Your Reaction? 0 0 0 0 0 0 These two showed surprisingly strong chemistry in the 2010 romantic comedy Crazy, Stupid, Love, so we were excited to see them reteam as love interests again in the far grittier Gangster Squad last year. And we're still extremely jealous of Emma Stone. Source: Warner Bros. 7 / 23 Adam Sandler and Drew Barrymore What’s Your Reaction? 0 0 0 0 0 0 Their love story in The Wedding Singer is so sweet that we're glad Adam Sandler and Drew Barrymore romance each other again in 50 First Dates, which is a little bittersweet, but no less romantic. Plus, the setting — modern-day Hawaii — is a bit more appealing than the '80s. Source: Sony Pictures, Warner Bros. 8 / 23 Brad Pitt and Cate Blanchett What’s Your Reaction? 0 0 0 0 0 0 As a married couple in Babel, Brad Pitt and Cate Blanchett's characters have to undergo a near-tragedy to reconnect, whereas in The Curious Case of Benjamin Button, their characters share a little bit more of a romantic story. He ages backwards, she ages normally, but they meet in the middle and love each other the whole time. Source: Paramount Pictures, Warner Bros. 9 / 23 Jennifer Lopez and Ben Affleck What’s Your Reaction? 0 0 0 0 0 0 Ben Affleck and Jennifer Lopez's real-life love story may be a thing of the past, but their onscreen sparks live on in film — two of them! In Jersey Girl, they play a couple whose marriage is cut short by her death, and in Gigli, she's a kidnapper who's charmed by his bouffant. Which is more tragic? You decide. Source: Sony Pictures 11 / 23 Cameron Diaz and Tom Cruise What’s Your Reaction? 0 0 0 0 0 0 Given that Diaz's character in Vanilla Sky is so crazy, we're glad these two get a do-over in 2010's Knight and Day. This time, his character seems crazy because he's a spy, but in the end, they're just crazy about each other. Source: Paramount Pictures, 20th Century Fox 11 / 23 Jason Segel and Emily Blunt What’s Your Reaction? 0 0 0 0 0 0 One of the only bright spots of 2010's comedy Gulliver's Travels is the presence of Jason Segel and Emily Blunt, who play a pauper and the princess he's in love with. Thankfully, their chemistry gets more of a spotlight in The Five-Year Engagement, where they play an engaged couple destined for the altar — for better or worse. Source: Universal Pictures, 20th Century Fox 12 / 23 Scarlett Johansson and Hugh Jackman What’s Your Reaction? 0 0 0 0 0 0 Though they may not end up together in either Scoop or The Prestige, the equally attractive Jackman and Johansson share some pretty hot kisses on the big screen. Source: Focus Features, Disney 13 / 23 Elizabeth Banks and Paul Rudd What’s Your Reaction? 0 0 0 0 0 0 It seems that whenever Paul Rudd romances Elizabeth Banks in movies, he's pretty immature (in Wet Hot American Summer, he tells her she tastes like a burger mid-makeout; in Role Models, he's a petty man-child). Good thing Rudd is so charming that he can get away with it. Source: Universal Pictures 14 / 23 John Cusack and Catherine Zeta-Jones What’s Your Reaction? 0 0 0 0 0 0 They may break up in both America's Sweethearts and High Fidelity, but in each film, the characters of John Cusack and Catherine Zeta-Jones share an epic (or so they thought) love at one point. Source: Sony Pictures, Disney 15 / 23 Sandra Bullock and Keanu Reeves What’s Your Reaction? 0 0 0 0 0 0 In 1994, sparks flew between Sandra Bullock and Keanu Reeves in Speed, and when they reunited on screen in 2006, they slowed things down considerably. In The Lake House, they play a man and woman who fall in love despite being separated by a weird space-time continuum. Source: Warner Bros., 20th Century Fox 16 / 23 Bradley Cooper and Jennifer Lawrence What’s Your Reaction? 0 0 0 0 0 0 We first questioned the pairing of Lawrence and Cooper as love interests in Silver Linings Playbook, mainly due to their 16-year age difference, but their chemistry in the film blew us away. We're looking forward to seeing more of it on display when they play a married couple in upcoming Depression-era drama Serena. Source: The Weinstein Company 17 / 23 Reese Witherspoon and Paul Rudd What’s Your Reaction? 0 0 0 0 0 0 Reese Witherspoon and Paul Rudd's first onscreen romance came in 1998 with the straight-to-video movie Overnight Delivery. In it, she plays a stripper who vows to help him with his girlfriend issues, only to eventually fall in love with him. When she plays a down-on-her-luck softball player in How Do You Know, it's a similarly odd, complicated road that eventually leads them to love. Source: Columbia Pictures, New Line Cinema 18 / 23 Julia Roberts and Clive Owen What’s Your Reaction? 0 0 0 0 0 0 Julia Roberts and Clive Owen are first brought together for a twisted, complicated relationship in 2004's Closer. Things aren't exactly easy for them in Duplicity, either, when they're not quite sure whether they can trust each other. Source: Columbia Pictures, Universal Pictures 19 / 23 Charlize Theron and Keanu Reeves What’s Your Reaction? 0 0 0 0 0 0 Charlize Theron finds herself sick during both of her onscreen romances with Keanu Reeves. First, she's mentally ill in The Devil's Advocate, driven to insanity, and then she struggles with a terminal illness in Sweet November — two not-so-happily ever afters. Source: Warner Bros. 20 / 23 Jon Hamm and Kristen Wiig What’s Your Reaction? 0 0 0 0 0 0 Jon Hamm and Kristen Wiig first sparked an onscreen romance in 2011 with Bridesmaids, followed soon after by their marriage in Friends With Kids. Both of his characters are a bit flawed, and although their movie romances don't pan out, the pair obviously shares a special onscreen chemistry. Source: Universal Pictures, Roadside Attractions 21 / 23 Jennifer Aniston and Paul Rudd What’s Your Reaction? 0 0 0 0 0 0 Jennifer Aniston first falls in love with Paul Rudd — onscreen, that is — in 1998's The Object of My Affection when he plays her gay best friend. More than a decade later, the pair reunited for Wanderlust as a married couple looking to escape Manhattan. Source: Universal Pictures, 20th Century Fox 22 / 23 Julia Roberts and Tom Hanks What’s Your Reaction? 0 0 0 0 0 0 Sparks first fly between Tom Hanks and Julia Roberts in 2007's Charlie Wilson's War when they play a romantically linked Congressman and socialite. Four years later, the duo reunites for a quirky, teacher-student love affair in Larry Crowne. Source: Universal Pictures 23 / 23 Movie Couples: Stars Who've Paired Up Multiple Times originally posted on POPSUGAR Entertainment 0 0 0 0 0 Back to Homepage Read More MoviesLeonardo DiCaprioBuzz SlideshowKate Winslet Kate Winslet The EGOT: Which Stars Are Almost There? 1 week ago Surprise! 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Lots more too if you want to cover anyone from more than the last 30 years. troyalg 2 weeks Paul Rudd gets around! lol Laurence15400731 3 weeks Paul Rudd is one lucky man! He got to hook-up with three Hot, Sexy women not once but twice. Stefania15346177 3 weeks WHAT ABOUT JENNIFER GARNER AND MATTHEW MCCONAUGHEY? Ghost of Girlfriend's Past and Dallas Buyers Club anyone?