True Romance
The 20 Best Date Flicks Around
Written by: Ryan McNally


After a candlelit dinner and a nice bottle of wine, there's nothing like a classic love story to keep the romantic mood flowing. Here are 20 unforgettable movies, alternately funny, tearjerking and sexy, that make for great date-night viewing. If you can't get busy after watching one of these flicks, then frankly you're beyond our help. Best of luck.
1. An Affair To Remember
Cary Grant and Deborah Kerr star in this 1957 romance classic, referenced in Sleepless In Seattle, about two strangers who meet on an ocean liner, fall in love, and agree to meet in six months atop the Empire State Building. Will they both show? Better grab some tissues...
2. Annie Hall
Woody Allen directed this 1978 romantic comedy classic, a Best Picture winner, about a quirky comedian (played by himself) who lives in Manhatten and falls for a Midwestern transplant (Diane Keaton). Terrific directorial touches and great dialogue make this a winner.
3. Breakfast At Tiffany's
Audrey Hepburn is superb as the lead in this 1961 classic directed by Blake Edwards. Despite her outward beauty and urban chic, there's a lonely heart below the surface, a fact that comes to light in her relationship with an upstairs neighbor.
4. The Bridges Of Madison County
Clint Eastwood masterfully directs this film, based on the best-selling novel, about a photographer and farmer's wife who enter into a four-day affair that forever alters both their lives. Superbly acted by Eastwood and Meryl Streep.
5. Casablanca
This deserving classic pits an intriguing love triangle against the backdrop of war to unforgettable effect. Ingrid Bergman and Humphrey Bogart are a perfect match, and Bogie is the kind of hard-drinking, cynical character ("I stick my neck out for nobody") that any guy can get behind.
6. The English Patient
During the waning days of World War II, a wounded soldier (Ralph Fiennes) tells a sympathetic nurse (Juliette Binoche) the epic tale of his doomed love affair with a married woman (Kisten Scott Thomas). 1996 Oscar winner for Best Picture.
7. Four Weddings And A Funeral
This witty British charmer stars Hugh Grant as a philandering bachelor, and Andie McDowell as the woman with whom he enters into a lengthy affair. A winning romantic comedy that's alternately funny and heartbreaking.
8. Gone With The Wind
There's a reason this epic Civil War drama is one of the all-time highest grossers and still beloved after more than 60 years - and much of it is due to the romance and its core between Clark Gable and Vivien Leigh.
9. Harold And Maude
More adventuruous movie fans looking for something a little different on Valentine's Day should seek out this cult classic, which stars Bud Cort as a teen misfit who finds a kindred spirit in an eccentric elderly woman (played by the excellent Ruth Gordon).
10. Jerry Maguire
Tom Cruise, a cute little kid, and football - this acclaimed romance has plenty going for it, including crisp writing and direction by Cameron Crowe, a star-making performance by Renee Zellweger, and an Oscar winning supporting turn by Cuba "Show Me The Money" Gooding Jr.
11. Moulin Rouge
The dance numbers and songs in this postmodern musical are brought to life by Baz Luhrmann's outstanding direction and fantastic chemistry bewteen the film's two attractive leads, Nicole Kidman and Ewan McGregor. (For a full review of this film, click here.)
12. An Officer And A Gentleman
Richard Gere and Debra Winger are the smoldering couple at the heart of this film, which boasts a memorable smooch between the two. Bonus for the guys: Getting to hear Oscar winner Louis Gossett Jr.'s legendary "Steers and queers" rant.
13. The Philadelphia Story
With a love triangle featuring screen legends like Katherine Hepburn, Cary Grant and Jimmy Stewart, how can you possibly go wrong? This 1940 romance classic also boasts witty dialogue and crisp direction courtesy of Geoge Cukor.
14. Pretty Woman
Julia Roberts became a star with her stellar turn in this Cinderella tale about a prostitute (Roberts) and a wealthy, formerly heartless businessman (Richard Gere) who gradually falls in love with her and rediscovers himself in the process.
15. Say Anything
The pinnancle of teen romances, this sharply written and directed pic by Cameron Crowe stars John Cusack and Ione Skye as kids from the opposite ends of the track who find an unlikely bond in one another. Features the lengendary "boom box" scene. (For a full review of this film, click here.)
16. Sense And Sensibility
Jane Austen's classic tale of 19th century manners, morals and romance gets the royal big screen treatment. It's directed by Ang Lee (Crouching Tiger, Hidden Dragon) and stars Emma Thompson (who also wrote the script), Kate Winslet and Hugh Grant.
17. Shakespeare In Love
This touching, smartly written romance about a young William Shakespeare (Joseph Fiennes) and his muse (Gwyneth Paltrow) captured the Best Picture Oscar in 1998. The excellent supporting cast includes Judi Dench, Ben Affleck and Geoffrey Rush.
18. Sleepless In Seattle
Nora Ephron directs this romantic comedy about a woman living in Baltimore (Meg Ryan) who hears a grieving widow (Tom Hanks) telling his tale on the radio, and falls in love with him. The likable performances by Ryan and Hanks, as well as the allusions to other clasic romances, make this a winner.
19. Titanic
Director James Cameron weaves a tragic romance into his epic tale of the Titanic's sinking in this Best Picture winner that's also the highest-grossing film of all-time. Teen heartthrob Leonardo DiCaprio and Kate Winslet play the doomed leads.
20. When Harry Met Sally
Can men and women ever really be friends? That's the question at the heart of this crackling romantic comedy, terrifically acted by Billy Crystal and Meg Ryan and featuring the infamous "fake orgasm" scene. (For a full review of this film, click here.)
Bonus Pick! Amelie
If you're going to venture out to the cineplexes this Valentine's Day, check out this new romantic comedy classic. A French film set in Paris, it features eye-popping visuals, a whimsical tone, and a winning lead performance by Audrey Tautou. (For a full review of this film, click here.)


Need more date-flick suggestions? Check out our 10 honorable mention picks: Bed Of Roses, The Bodyguard, Emma, Like Water For Chocolate, Love & Basketball, Love Story, The Princess Bride, A Room With A View, Singles and So I Married An Axe Murderer.

Did we forget your favorite date flick? Drop us a line and tell us which of our picks you agreed with, and which classic romances you think we missed.

You can pick up any of these movies by clicking on the corresponding film image above.


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