When Harry Met Sally (1989)
Synopsis: Harry (Billy Crystal) and Sally (Meg Ryan) meet while sharing a ride to New York after graduating from the University of Chicago. This classic movie follows the pair through their lives as they each search for love but keep bumping into the other instead.
Why you'll both like it: The witty banter from both main characters makes this classic friendship-turned-romance a must-see.
Date Night (2010)
Synopsis: What begins as a glamorous and romantic date night for Phil and Claire Foster (Steve Carell and Tina Fey) turns into a much more adventurous evening after a case of mistaken identity.
Why you'll both like it: The unexpected twists and action scenes appease the romantic and action-adventure enthusiast alike.
50 First Dates (2004)
Synopsis: Commitment-phobe Henry Roth (Adam Sandler) thinks he's found the girl of his dreams in Lucy Whitmore (Drew Barrymore) after their first date. After he discovers she suffers from short-term memory loss, he soon realizes that first impressions count for a lot more with her than he originally anticipated.
Why you'll both like it: Adam Sandler is everything you expect -- charming and goofy (and guy-friendly) at the same time.
Synopsis: Alex Hitchens (Will Smith) makes his living as a professional date doctor, but finds the love advice he gives to other people doesn't work so well on the gossip columnist he has his eye on.
Why you'll both like it: Your guy might think it's just another romantic comedy, but there are plenty of big laughs in this movie.
The Proposal (2009)
Synopsis: In order to avoid deportation to Canada, book editor Margaret Tate (Sandra Bullock) hatches a scheme to get her assistant, Andrew Paxton (Ryan Reynolds), to marry her. A skeptical immigration agent hardly believes her story, so the new "couple" must learn as much as they can about each other -- while spending a hilarious weekend with Paxton's family in Alaska.
Why you'll both like it: The entire movie is full of laughs as Margaret and Andrew try to keep their faux engagement a secret from his family, and Betty White's character is especially hilarious.
Can't Buy Me Love (1987)
Synopsis: A young Patrick Dempsey plays Ronald Miller, a nerdy teenager who pays Cindy Mancini (Amanda Peterson), the most popular girl in school, to pretend to be his girlfriend so he can break into the "cool" crowd. As the ploy goes on, Cindy's growing feelings for Ronald go unnoticed as he becomes consumed by his newfound popularity.
Why you'll both like it: Classic '80s movies about high school drama offer nostalgia and you¿ll enjoy Dempsey's pre-"McDreamy."
Say Anything (1989)
Synopsis: Lloyd Dobler (John Cusack) and Diane Court (Ione Skye) make an unlikely couple the summer after the two graduate high school; he tries to win her love despite the objections of her over-protective father and her departure for England at the end of the summer.
Why you'll both like it: The scene where Lloyd holds the boom box over his head to get Diane's attention is a can't-miss classic.
Valentine's Day (2010)
Synopsis: More than a dozen residents of Los Angeles, some in relationships and some not, navigate Valentine's Day from early morning until midnight, each dealing with the pressures and expectations of the romantic holiday.
Why you'll both like it: You'll both recognize big-name actors, such as Jessica Alba, Ashton Kutcher, Patrick Dempsey, and Jennifer Garner (among others).
Love Actually (2003)
Synopsis: Love begins and ends -- and sometimes begins again -- for eight different London couples, set during the frantic month before Christmas. Multiple story lines intersect and favorite actors, such as Hugh Grant and Liam Neeson, clearly have a good time in the flick.
Why you'll both like it: You'll love the British setting and Colin Firth; he'll love Keira Knightley.
10 Things I Hate About You (1999)
Synopsis: Shakespeare's "The Taming of the Shrew" is set in a modern-day high school in this fun '90s film. Bad boy Patrick Verona (Heath Ledger) accepts the challenge of dating ill-tempered and rebellious Kat Stratford (Julia Stiles), all so Kat's popular younger sister will be allowed to date per their over-protective father's house rule.
Why you'll both like it: Shakespeare's themes are classic and this update gives romance and courting a fresh, funny spin.
500 Days of Summer (2009)
Synopsis: It's love at first sight for Tom Hansen (Joseph Gordon-Levitt) when he meets Summer Finn (Zooey Deschanel), the new administrative assistant at his greeting card company. Tom sees his soul mate; Summer sees something lighter. When their whirlwind romance ends he reflects back on the days he spent loving and hating Summer in an attempt to put it all behind him.
Why you'll both like it: Your guy will like it because it's told from Tom's perspective, and you'll both love the adorable Zooey Deschanel.
Crazy Stupid Love (2011)
Synopsis: After his wife asks for a divorce, Cal Weaver (Steve Carell) attempts to navigate the single scene with the help of his new friend Jacob Palmer (Ryan Gosling), while juggling his relationships with his children and ex-wife.
Why you'll both like it: You'll both chuckle at Carell's dorky character in the scenes beside Gosling's suave one.
The American President (1995)
Synopsis: Romance proves tricky for widowed American president Andrew Shepherd (Michael Douglas) when he falls for fiery environmental lobbyist Sydney Ellen Wade (Annette Bening) during the intense period before election season.
Why you'll both like it: Michael Douglas gives some great one-liners that you'll both enjoy.
One Day (2011)
Synopsis: July 15th is a special date for Dexter and Emma (Jim Sturgess and Anne Hathaway) -- it's the day after their college graduation and the day they decide to be friends after spending the night together. The tumultuous film shows the pair -- sometimes growing closer, other times growing far apart -- on the same day each year for 20 years.
Why you'll both like it: The scenery -- Scotland, London, and Paris -- is spectacular, and the true-to-life tale of the ebbs and flows of a relationship will ring true for both of you.
The Princess Bride (1987)
Synopsis: This humor-filled fairy tale, read by a kindly grandfather to his ill grandson, is a classic story of love and adventure complete with a beautiful princess, an evil prince, a pirate, a giant, and a skilled swordsman determined the find the man who killed his father.
Why you'll both like it: This ridiculously funny flick isn't just your average romantic fairy tale.