One of the biggest problems when picking a movie for any group of people is that it’s so hard to please everyone; when you’re on a date, it’s made a little worse because the fate of any relationship may rest on this pick. It probably won’t ruin your chances altogether, but selecting a bad movie can alter the tone of the evening. Your tastes may vary but in my book, a good date movie should have a little romance and a lot of humor, and something that can provoke conversation later. You can’t always pick the perfect movie, but if you don’t know what they’re into, here are a few suggestions that might help you get started:
Stranger than Fiction
Will Ferrell is an actor who is unfortunately cast often to play a loud and slightly stupid character–as a result, he can be a bit of a turn-off to anyone who doesn’t much care for loud and stupid people. This film really is an example of his range as an actor, as he plays instead the quiet, mumbling Harold Crick: a tax auditor who starts to hear his life narrated by a woman with an English accent. He’s convinced he’s going a little crazy, but becomes really concerned when she announces that he is going to die. Meanwhile, an English writer is having writer’s block–as she can’t quite figure out how to kill off the protagonist in her new novel. Dustin Hoffman comes in as a literature professor Harold consults for information on his situation, Queen Latifah is a new assistant for the authoress, and Maggie Gyllenhaal appears as a woman Harold’s supposed to be auditing, but finds himself falling for. All in all, it’s a surprisingly smart, funny, and romantic film that is easily one of my all-time favorites.
It is really, really hard not to like Will Smith. Whether he’s kicking the snot out of some aliens, vampires or robots, raising hell in Bel-Air, or raising a son in New York, he is an incredibly likable guy. In Hitch, he is the eponymous character who nervous men can hire to help them win the women of their dreams. Kevin James shows up as a man Hitch claims will be his Sistene Chapel–his masterpiece–an awkward financial manager who’s smitten with a wealthy heiress. While things seem to be going well for his pet project, Hitch can’t quite seem to get his dates right with a journalist researching the rumored Date Doctor. There’s even a ‘Hey, it’s that guy!’ moment with Burn Notice star Jeffery Donovan as one of the main sources of conflict for the characters. It’s a solid film with Smith’s characteristic sense of humor that makes it both entertaining, and likely one of the modern classics.
50 First Dates
Continuing with the theme of typecast actors getting a chance to show their range, Adam Sandler gets the opportunity to woo Drew Barrymore in this quirky romance I’ve described as ‘the Memento of Romantic Comedies’. Full of gorgeous shots of Hawaii, the film follows Sandler’s character falling for a woman who doesn’t remember anything that happens from day to day–a version of Anterograde Memory Loss. When he meets her, she actually relives the same day over and over, because of her condition (which she is not aware of). Thus, each day he meets her is like their first date, and he must win her over every single day. As it moves from quirky humor flawlessly to moving moments, the film is a pretty unique look at love, and told by a guy most men can appreciate.
Benny & Joon
A lot of men say it’s okay to have a man-crush on Johnny Depp; if you were previously neutral to him this may be the film that pushes you over the edge. This incredibly quirky comedy chronicles the lives of Benny and Joon Pearl, a brother and his eccentric, troubled younger sister. When they win the cousin of one of Ben’s friends in a poker game, the lovable and unusual Sam (Depp), he wins both Pearls over and starts to fall for Joon. Benny is at first reluctant, but is later won over by an excellent slaptstick routine in the park, and as he sees how well Sam takes all of Joon’s oddities in stride. While it is in title a film about that brother-sister team, Johnny Depp really steals the show. It’s one of the more unique films I’ve seen in a while.
When all else fails, there is also:
The Princess Bride
I have never met a person who has said they dislike this movie–probably a handful of people out there, but I have simply never met them. Male, female, young and old, this movie holds an incredibly special place in most people’s hearts. A little action, a bit of humor, a classic romance, and a cast of classic characters. For most people, this movie is like an old friend. Not among the initiated? The story is a sort of medieval romance between a stable boy who is called to war, away from his lover and employer, Buttercup. While away, she is told he’s dead and pressured into marrying the Prince of the kingdom, Humperdink–who has a fairly nefarious plan for her. Along the way, she is kidnapped by a misfit gang of mercenaries, all of whom are pursued by a mysterious man in black. Cary Elwes and Andre the Giant are among the more memorable roles, and Mandy Patinkin’s role has permanently glued a line into the pop culture catalog: “Hello, my name is Inigo Montoya. You killed my father. Prepare to die.”
A few Honorable Mentions:
Better Off Dead -In order to win his girlfriend back, John Cusack’s character–the unsuccessfully suicidal Lane Meyer–organizes a ski race with his main competitor for her affections. A classic of the eighties overshadowed by the more famous Ferris Beuller’s Day Off, this is an incredibly funny movie for those who can appreciate a little dark humor mixed in with their romances.
Love Actually – One of Britain’s finest films, it is not so much a love story as a series of stories which kind of meet and intertwine. I see it as a treatise on love, and all of its types: romantic, sexual, pure, fraternal, familial, unrequited, etc. A beautiful work on the various obstacles to love, all told with the dry British sense of humor and irony.
The Reduced Shakespeare Company: The Complete Works of William Shakespeare, Reduced – A little harder to find, but what’s more romantic and intellectual than Shakespeare? How about watching three guys humorously summing up and joking around about The Bard and some of his most famous works? The DVD captures a stage performance of their show, and is probably one of the more unique ideas for a good date.
Word of caution: it helps to have read a fair amount of Shakespeare to get some of the jokes.