Top 10: Date Movies

The blissful early days of a relationship are a wondrous time of discovery and pent-up sexual energy that can leave you deliriously happy and flat broke. It doesn’t always have to be $200 meals, since staying in with a movie is one of the cheapest dates around. The success of that date, and how far you get with her afterward, depends largely on your choice of movie. Sorority House Massacre isn’t going to cut it, nor will anything too serious. And if you rent something overtly sexual, be prepared for two hours of extreme awkwardness.

It’s a veritable minefield, but we’re prepared to help you navigate through it. Perfect date movies should have something for both of you, with an attractive cast, romance, action, laughs, and maybe a tame sex scene. You can always cop out and go the safe route with something predictable (and atrocious) like You’ve Got Mail, but you’d be better off with one of these unique options. You’ll get high marks for originality and won’t have to put up with Meg Ryan. So sit back, snuggle up with your new girl and enjoy one of these top 10 unique date movies.

Number 10

Jerry Maguire - 1996

Back before he went completely insane, Tom Cruise was the biggest box-office star in Hollywood and the charisma and screen presence that allowed him to climb to this lofty position is on full display in this hybrid romantic comedy/sports movie. Directed by Cameron Crowe (Almost Famous, Singles), Jerry Maguire tells the tale of a ruthless sports agent who suffers a sudden change of heart and turns his back on the money-crazed industry.

3 reasons she’ll love it: Jerry Maguire has the three pillars of success as far as date movies are concerned: Pre-crazy Tom Cruise, it’s a love story in which the average-looking girl gets the “hot” guy and kid so cute you’ll want to punt him.

3 reasons you’ll love it: There’s great sports action, tons of fantastic cameos (from Glenn Fry to Troy Aikman) and a surprisingly hot sex scene with Kelly Preston (all date movies should be so blessed).

Number 9

The Apartment - 1960

Jack Lemmon, Shirley MacLaine

You can advance your career through hard work, long hours and ample ass-kissing. Or, if you are Bud Baxter (Lemmon) in this classic among 1960s date movies, you just let all the executives use your Manhattan apartment for their illicit trysts. That’s the premise of this long-forgotten comedy from legendary director Billy Wilder (Some Like It Hot). Things go along swimmingly for Bud until he falls for the mistress of his boss -- which understandably makes things awkward.

3 reasons she’ll love it: The hilarious backward attitudes toward women will make her happy for today’s more progressive mindset, she’ll giggle at the style -- handsome men in thin ties, and Shirley MacLaine’s ditzy, whorish character will make her feel morally superior.

3 reasons you’ll love it: Lemmon’s sad-sack, faceless corporate drone will let you look at your predicament and remember that it could always be worse. The Apartment provides a look at the good old days when cigarettes were smoked in your office and women were called “dames.” You’ll also earn major bonus points for introducing her to a hilarious silver-screen classic that helped shape the genre of date movies.

Number 8

Belle Epoque - 1992

Penelope Cruz, Miriam Díaz Aroca

Show off your cultured continental side and rent this 1994 Oscar-winner for Best Foreign Language Film. It tells the story of a Spanish soldier who deserts the army and ends up in a villa with an artist and his four serious hot Spanish daughters. Hmm, risk your life on the front lines or hang out with four farmer’s daughters? It’s sexy without being raunchy and funny without resorting to poop jokes -- just as all date movies should be.

3 reasons she’ll love it: Your date will love the gorgeous Spanish scenery, the sensual sex scenes and the cute guys with even cuter accents.

3 reasons you’ll love it: It’s basically a two-hour cinematic version of the age-old farmer’s daughter fantasy, when your date takes a pee break you can freeze-frame nude scenes of Penelope Cruz, and of course, there’s Penelope Cruz.

Number 7

About a Boy - 2002

Hugh Grant, Rachel Weisz



For many women, dating is really just a job interview for prospective fathers. So, your girl will undoubtedly be watching how you judge Hugh Grant’s character in this pleasant little flick. He starts off as a lazy, womanizing boy-toy, but after becoming an unlikely and unwilling surrogate father to a bastard child in this date movie bloodbath, he turns into a model adult man.

3 reasons she’ll love it: For once she gets to witness a man who can be changed for the better, the female lead isn’t a size zero with porcelain skin, and the cute, awkward lead boy.

3 reasons you’ll love it: You’ll envy Hugh Grant’s bachelor pad, enjoy the soundtrack (performed exclusively by Badly Drawn Boy), and Rachel Weisz.

Number 6

Mr. & Mrs. Smith - 2005

Brad Pitt, Angelina Jolie



Make-up sex is just about the best kind of sex you can have. So, imagine how good the sex is between Brad Pitt's and Angelina Jolie’s characters after they spend 20 minutes trying to kill each other. That sexual tension, combined with many more phenomenal action sequences, make this one of the best date movies to come along in a long time. With an A-plus cast comes huge expectations, but even with that burden, director Doug Liman (Swingers, Jumper) delivers.

3 reasons she’ll love it: Your date will love the spectacularly decorated suburban home, the rare and empowering presence of a hit woman and, as usual, Brad Pitt.

3 reasons you’ll love it: You’ll love the coolest weapon arsenal seen on the screen in some time, the amazing car chase (between BMWs and a minivan) and, as usual, Angelina Jolie.

Number 5

Say Anything - 1989

John Cusack, Ione Skye

Lloyd Dobler (John Cusack) did more than just bag the hot popular rich chick while wearing a trench coat; he also gave hope to helpless nerds the world over. And this '80s date-movie classic tells the tale of how he did just that. You can’t help but cheer for Dobler because not only is he the consummate underdog, he’s also a father figure to his little brother and boasts the coolest ghetto blaster in movie history. So, to see him win in the end will melt even the coldest heart.

3 reasons she’ll love it: No woman can resist the young and charming John Cusack. She'll also like the endearing father/daughter relationship and the hilarious ‘80s fashion.

3 reasons you’ll love it: You’ll like the hot chicks wearing hilarious ‘80s fashion, the retro soundtrack and the sport of the future.

Number 4

Intolerable Cruelty - 2003

George Clooney, Catherine Zeta-Jones




Not all date movies have to come slathered in cheesy romance, especially when they star two of the hottest actors this side of 2000. George Clooney plays a hardened divorce lawyer who falls for a client (Catherine Zeta-Jones) and tries like mad to get in her legal briefs. It’s filled with cheating husbands and gold-digging ex-wives, which could make you ask why it belongs on this list. Well, aside from being one of the wittiest romantic comedies out there, it also captures the same flirtatious energy both you and your friend are hopefully feeling on your movie-watching date.

3 reasons she’ll love it: Obviously, she’ll like People magazine’s twice-named Sexiest Man Alive, George Clooney, a female character that can go toe-to-toe with the slimiest lawyers and con artists out there, and all the cheating men who get their comeuppance.

3 reasons you’ll love it: You’ll love it for the rare and dignified beauty of Catherine Zeta-Jones, the Coen Brothers’ eclectic style and an asthmatic contract killer.

Number 3

The Wedding Singer - 1998

Adam Sandler, Drew Barrymore



Usually, lead singers of wedding bands are the kinds of guys you’d like to drag out behind the banquet hall and strangle with a microphone cord, but Adam Sandler’s Robbie is entertaining enough to avoid such a fate. He and a less-annoying-than-usual Drew Barrymore star in this charming romantic comedy and play star-crossed lovers who find themselves engaged to the wrong people. Sandler and Barrymore stick to the moral high ground and wait for the inevitable happy ending to begin their relationship.

3 reasons she’ll love it: She’ll revel in an unrivaled ‘80s soundtrack, be thankful her fingers will never get tangled in a mullet and laugh at the horrific bridesmaid dresses.

3 reasons you’ll love it: Guys will appreciate the realistic portrayal of life as a freshly dumped dude, like the hot girls (if you consider girls with feathered hair and neon sweatshirts hot), and love the fact that the movie ends after 95 minutes.

Number 2

Bull Durham - 1988

Kevin Costner, Susan Sarandon



Sports movies usually make good date movies, thanks in part to their combination of action and romance. This baseball flick, however, adds some spicy sex and above-average dialogue to elevate it into the classic realm. Kevin Costner plays a career minor league catcher called on to mentor a dim yet talented prospect (Tim Robbins). Along the way, the two fight over the affections of Annie Savoy (Susan Sarandon), a townie with a thing for ballplayers.

3 reasons she’ll love it: Your girl will like the liberal female lead who’ll make her feel empowered (which could make things very interesting if things get a bit frisky), the cute baseball players, and Kevin Costner’s list of the important things in life, which range from hanging curveballs to high fiber, and ends with an admiration of “long, slow, deep, soft, wet kisses that last three days.”

3 reasons you’ll love it: You’ll chuckle at Nuke LaLoosh’s cliche-ridden interviews, but you’ll enjoy how the movie portrays life in the minor leagues, and the old-fashioned, dirt-on-your-uniform, pine-tar-in-your-hair baseball action.

Number 1

Hitch - 2005

Will Smith, Kevin James



There are life coaches, financial consultants, career counselors, and all other sorts of people willing to offer their services, but is there any help out there for a hapless dweeb with no clue about women? There is in this surprising rom-com, and it is in the form of a silky-smooth Will Smith who mentors Kevin James on the subtleties of dating in the new millennium. We mentioned that a good date movie should have laughs, and this film has a black book full of them.

3 reasons she’ll love it: She’ll like Will Smith doing his Will Smith thing, Kevin James’ attempt at dancing and the flick gives an inside look at the inner-workings of a man on the prowl.

3 reasons you’ll love it: You’ll like Eva Mendes, the truly valuable nuggets of dating advice from a master and Eva Mendes (no, that’s not a misprint).

date movie climax

How many first heavy-petting sessions have taken place on the couch with the soft flicker of a TV illuminating the groping couple as the DVD’s menu music plays in a continuous loop in the background? A movie at home is an ideal date -- it’s simple, cheap and easily transferable to second base and beyond. It must be done correctly, however, and trying some of these 10 unique date movies will give you a fighting chance. The rest is up to you, stud.