Choosing the perfect movie for a date can be a delicate art, especially if you and your date have mismatched taste. You don't want to bring a Guy Maddin film to a date with a person whose all time favorite movie is Miss Congeniality 2: Armed and Fabulous or the Scorpion King (though you might question why you are going out with them in the first place). You also want something that sets the mood properly- light, fun, slightly offbeat, and romantic but not setting the bar too high. Compiled below are movies that I would proudly take to a date. Not all titles will appeal to everyone, but would you really want to date someone who didn't like The Apartment? I'm just doing you a favor!
All the Real Girls (2003). It's risky to watch a movie that is, in part, about love gone wrong. But All the Real Girls also shows the fun of falling in love. And it stars two of cinemas most crush worthy actors: Paul Schneider and Zooey Deschanel. Plus you'll get major indie cred for a choosing a movie directed by David Gordon Greene. Oh, and the love scenes are pretty hot too.
Find it in the catalog!
Annie Hall (1977). If you and your date are just the slight bit neurotic or bookish, odds are you will relate immensely to this movie. This is Woody Allen at his most charming; you almost understand why the ditsy but beautiful Annie (Diane Keaton) would fall for him. Annie Hall is full of relationship foibles, but still optimistic and funny.
Find it in the catalog!
The Apartment (1960). You can't really go wrong with Billy Wilder and this is my favorite of his films. A romantic comedy about poor lovelorn C.C. Baxter (Jack Lemon), who lets the higher ups in his office use his apartment to carry out their extramarital affairs. This helps him get ahead at work, but he starts to question the morality of his actions when he sees how infidelity affects the elevator operator of his dreams (Shirley MacLaine).
Find it in the catalog!
Grosse Pointe Blank (1997). One of the few action-romantic comedies that manages to be pretty good. It follows hit-man Martin Q. Blank (the ever-dreamy John Cusack) as he returns home to attend his high school reunion. While in town, he attempts to reconnect with his ex-girlfriend (Minnie Driver) whom he abandoned on prom night. However, he also has to fend off several stalkers including a Basque Terrorist and two National Security Agents who want him dead.
Find it in the catalog!
Groundhog Day (1993). This has to be one of the sweetest and funniest rom-coms of all time. Bill Murray plays a self-absorbed and cranky TV weatherman named Phil Connors who is horrified to find that he is doomed to repeat February 2 over and over again in the small town of Punxsutawney, PA. During this eternal Groundhog Day, Phil finds himself developing feelings for his annoyingly nice and upbeat producer Rita (Andie MacDowell) and he begins using his time to turn into the kind of man she could love.
Find it in the catalog!
In the Mood for Love (2000). The film follows two neighbors Mrs. Chan (Maggie Cheung) and Mr. Chow (Tony Leung), who strike up a friendship after they find out that their spouses are involved in an affair. Both are determined not to make same mistake. It's a sexy and passionate film, but the two stars barely touch. Instead it's full of longing, brooding and atmosphere.
Find it in the catalog!
Kiss Kiss Bang Bang (2005). A tongue and cheek action comedy that helped revive Robert Downey Jr.'s career and it's easy to see why. His performance here is loaded with charm and charisma. Downey Jr. plays actor Harry Lockhart who is following a private detective, Gay Perry (Val Kilmer), as research for a role. Along the way, Harry finds himself doing actual dangerous detective work when his high school crush (Michelle Monaghan) asks him to investigate the death of her sister. This is a cute and funny spoof of film noir.
Find it in the catalog!
Out of Sight (1998). A fun, romantic, caper movie by director Stephen Soderbergh, this movie stars Jennifer Lopez as U.S. Marshall Karen Sisco. Sisco is a smart and capable police officer, but she still finds herself falling for charming career bank robber Jack Foley (George Clooney). Foley is not the brightest, which is why he frequently gets caught in his schemes and he hits on a U.S. Marshal. Still he looks like George Clooney, so you can understand the attraction. Lopez and Clooney have steamy chemistry together; it's easy to forget how charming Lopez can be. Foley plans on robbing a diamond from a wealthy business man and Sisco must decide where her loyalties lie- with Foley or the law. The hotel bar scene in this movie is one of my favorite moments.
Find it in the catalog!
The Philadelphia Story (1940). A screwball romantic comedy starring Cary Grant, Jimmy Stewart, and Katherine Hepburn. No one does screwball better than Grant and Hepburn, so this is a pretty safe bet. It's witty, fun and a classic!
Find it in the catalog!
Punch-drunk Love (2002). This is probably the most controversial of the bunch, as it's arty and sometimes dark. Still, I think movie is pretty good date litmus test for film geeks. Paul Thomas Anderson is great at depicting romances between characters who are heavily damaged. Here Adam Sandler plays Barry Egan, a man with anger problems, who falls in love with his sister's coworker (Emily Watson). Barry must overcome both personal and external issues (he's being harassed by extortioners) for the romance to succeed. A sweet and surreal movie.
Find it in the catalog!
Tootsie (1982). The premise of Tootsie is so gimmicky that you could see it being a movie starring Kate Hudson and Gerard Butler (I'd definitely like to see Butler try drag). Luckily the writing and acting far out shine the gimmick. Dustin Hoffman gives one of his best performances as Michael Dorsey/ Dorothy Micheals and given his career, that's a pretty high bar. No wonder Liz Lemon chose it to watch on her first date with Floyd (her best boyfriend yet) on 30 Rock!
Find it in the catalog!
Shaun of the Dead (2004). This is definitely more of a guy movie as it's largely about the friendship between Shaun (Simon Pegg) and Ed (Nick Frost). Also, there is a lot of gore and zombie killing. However, girls as well as guys should like the humor in this movie . Pegg and Frost's other buddy movie, a police action comedy called Hot Fuzz, is also another good choice.
Find it in the catalog!
