Category Archives: Dating

Ah, which movie to watch, for which relationship, on which date? There are a million possible combinations; the movies talked up here are simply reliable dating workhorses, agreeable to both men and women in the full flush of mating season, but also tasteful, witty, and a little sex-minded. One must never neglect the power that the right movie, seen by the right couple, at the right stage in their courtship, can have—not merely on the current state of that relationship, but also on its course in years hence—any of these could become an “our movie,” like an “our song,” and fuel passionate allegiance for a lifetime. Or, if you’re just dating, they’re simply dynamite movies that happened to have men, women, and love stuff in them.

Fever Pitch (2005)

Fever Pitch (2005 film)
Fever Pitch (2005 film) (Photo credit: Wikipedia)

Perhaps date movies shouldn’t be about people who are dating at all, since films that focus on relationship strife provoke questions of rights and wrongs, guilt and innocence that viewers on a date might not want to get into. At least Fever Pitch (which is based on a much more cynical Nick Hornby novel that revolves around English football, not baseball) is relatively innocuous in this regard, if only because the main characters are both so adorable: Late Night TV favorite Jimmy Fallon is Ben, a humble schoolteacher who loves his job and the Boston Red Sox; Drew Barrymore is Lindsey, a high-powered business genius who’s looking for something better than the shallow corporate climbers she usually dates. Trouble occurs when she starts realizing that Ben just might not consider her as important as a bunch of overpaid jocks. (Note to male viewers: the correct response to this realization is not, “Yeah, so?”) The movie includes cameos by some of the 2004 Sox—who beat the odds and earned Boston a World Series victory for the first time in eighty-six years. (The last scenes of the film were rewritten and shot during the series to capitalize on this amazing turn of events—who coulda thunk it?).


Out of Sight (1998)

This might well be the best date movie ever made. You could watch this Elmore Leonard adaptation, in which George Clooney and Jennifer Lopez flirt like they’re in heaven together, again and again; it’s a perennial, and it’s inexhaustibly brimming with character bits, witty dialogue, and narrative invention. Crooks, cops, heists, and so on abound—but this movie is less about the plot than it is about the people—and that’s what dating’s about, really, isn’t it?

Jerry Maguire (1996)

Jerry Maguire
Jerry Maguire (Photo credit: Wikipedia)

A romantic comedy about a sports agent is, in concept, kind of like a musical about an arms dealer, but Cameron Crowe’s hit remains refreshingly witty, sharp, affecting, and—glory of glories—slick without being trite. A pleasurably humane and light-footed stroll through familiar territory, the movie at times smacks of a Ron Shelton or Paddy Chayefsky satire on the agenting industry, but in the end it’s too starry-eyed by half for that. Let’s face it: Tom Cruise is usually too good-looking and supercilious to be convincing as a normal, modest human being, but here, as a go-getter agent whose bread and butter are his empty smile and his spiel, he’s superb—suddenly, all of that self-love and amoral charm makes perfect sense. The dramatic crux is the hero’s midcareer crisis of integrity—a fit of self-loathing impels Maguire to write a “more heart, less profit” memo and distribute it around his bustling agency’s office. Of course, he’s summarily fired, but he manages to convince single-mom accountant Dorothy (Renee Zellweger) to come with him to help start up his own business. All of his clients drop him; all but one, that is—showboat Rod Tidwell (Cuba Gooding Jr., who won an Oscar for it), a wide receiver with more attitude than talent. Jerry Maguire may be the most femme-friendly sports movie ever made, and it manages that feat without resorting to bathos.

Before Sunrise (1995)

Jesse and Celine (Ethan Hawke and Julie Delpy), each alone and separately heartsick, meet on an aimless train ride through Austria, and decide to disembark and spend a day talking. That’s all there is to it—or, almost all—and yet this impossibly brilliant, moving film is a perfect date movie. Actually, it might be too perfect—does it raise expectations too high regarding just-met sparkling conversation, witty sex appeal, and intelligent soul sharing? Jesse and Celine seem preposterously and blissfully well suited for each other, no matter how messily realistic Richard Linklater’s screenplay is about emotional exchange—could their ease and confidence intimidate the naturally nervous dater? Perhaps—or maybe it’d help boil the water and get the gears greased. The socially handicapped might consider it a form of basic training to view this movie on (or even before) a date. Pay attention, pilgrims: this is how it is done. Better than its sequel, Before Sunset, and far, far better than the third time at bat with these characters, Before Midnight.

Defending Your Life (1991)

Cover of "Defending Your Life"
Cover of Defending Your Life

Once, Albert Brooks was the ultimate everyman schlemiel; here that schlemiel dies, and he’s uncomfortable even in the afterlife. This is a date movie? Well, he meets Meryl Streep, the only other recently deceased person under seventy, and as they each attend hearings before a purgatorial tribunal to examine their lives and determine if they have exhibited enough courage to “move forward” (think of it as Beverly Hills Buddhism), they fall in love, even though there’s no hope that they can ever be together. This is an especially appropriate film for nascent relationships—it’s funny but not raunchy, cute but not sticky. It’s probably best to plan for a dinner afterward; one of the clear benefits of spending time in Judgment City (which looks remarkably like Southern California) is that you can eat as much as you want and never gain weight, so there’s plenty of moaning over mounds of shrimp and piles of pasta.