On that first video date
1 Breakfast at Tiffany’s (1961, Paramount, unrated)
You can rent yet another contrived twentysomething romance, or you can choose this innocent, glamorous romp, the one that inspired them all. Audrey Hepburn is Holly Golightly, the prototypical club kid whose shallow life gets transformed by writer George Peppard.
2 Singles (1992, Warner, PG-13)
Befuddled lonelyhearts seek mates in grunge-ridden Seattle, which should immediately have you and your date counting your blessings. Cameron Crowe’s likable comedy pointedly shows how people so often screw up the simple task of falling in love.
3 West Side Story (1961, MGM/UA, unrated)
Everyone looks good renting this: It offers romance, action, production numbers, and Technicolor splendor throughout. Richard Beymer and Natalie Wood star as the lovers divided by sharply choreographed gang warfare. Although you may sigh at the unlucky pair’s doomed love, at least you can take comfort in the fact that cool outfits are forever.
4 Groundhog Day (1993, Columbia TriStar, PG)
For a clean-as-can-be romance, try this comedy, starring Bill Murray as a snide jerk who reforms to try to win a woman (Andie MacDowell) who’s too good for him. Even if you’ve both seen it before, joining in with its premise of a perpetually repeated day makes it even more fun the second time around.
5 The Evil Dead (1983, HBO, unrated)
No guts, no glory — that goes for dating and, often, moviemaking. The Evil Dead has plenty of guts, and everything else to make a couple laugh, jump, and end up in each other’s lap. And if things go well enough to warrant a second date, Evil Dead 2: Dead by Dawn is waiting at the video store.
6 Harold and Maude (1971, Paramount, PG)
Everyone wonders if it’s possible to find someone to love, and this dark comedy about a death-obsessed 19-year-old and his 79-year-old paramour makes a bizarre case for the affirmative. And hey, if they can make it work, surely you two can.
7 Play It Again, Sam (1972, Paramount, PG)
Woody Allen (who wrote the screenplay) plays a neurotic film critic who gets dating tips from Humphrey Bogart — thereby creating the perfect love story for film geeks everywhere. A remake would probably have Allen running a video store and getting advice from Quentin Tarantino.
8 The Shop Around the Corner (1940, MGM/UA, unrated)
If your date works in the same mall that you do, then check out the greatest retail love story ever. James Stewart and Margaret Sullavan star in this Ernst Lubitsch comedy as pen pals who don’t know each other’s identity, even though they’re sparring coworkers in a gift shop.
9 The Night Porter (1974, Sultan, R)
Dirk Bogarde is a former SS officer posing as a bellhop, and Charlotte Rampling is the guest he recognizes as a concentration camp survivor with whom he was once involved. As they renew their sexual relations, your date will think you’re intellectually complex or extremely kinky, either of which could work to your advantage these days.
10 Ulysses (1967, Mystic Fire, unrated)
If you thought James Joyce’s novel was boring when you read it in college, you won’t believe how tedious it is to sit through 120 minutes of film footage of Leopold Bloom (Milo O’Shea) hanging around Dublin. But you’ll sure look smart when you suggest renting it, and when the movie quits holding your attention, you can propose other activities.
By Jason Cochran, Steve Daly, Glenn Kenny, Lois Alter Mark, Chris Nashawaty, Tim Purtell, Michael Sauter, and J.R. Taylor