The Best Date Night Movies

Image via Universal

Starring: Rachel McAdams, Ryan Gosling, James Garner, Gena Rowlands

This one has it all: the star-crossed lovers from different social classes—she's an heiress, he's working class. When she moves away, he writes her every day for a year, but her mother intercepts the letters and hides them away. Every day for a year—365 letters, not one response. That right there is the kind of relentless romantic determination that lands you a restraining order in the real world. (Sidebar: Most Hollywood romances are tests created for men to see whether or not they're stalkers).

But wait! The movie is told in flashback. In the present day, the man is old but with-it, while the woman suffers dementia that comes and goes. This film often leaves people in such a heightened state of amorousness that they will mistake the slightest attraction for undying love. Do your best to be slightly attractive. —Josh Robertson

Starring: Tika Sumpter, Parker Sawyers

As if remembering that the Obamas are no longer the first family isn’t emotional enough, Southside With You will give you even more reason to love Michelle and Barack. This film memorializes the couple’s fateful first date in the Southside of Chicago in 1989, which started a relationship to be cherished forever, by both Michelle and Barack and the American public. A date movie about a date; how meta. —Mallorie List

Starring: Katherine Heigl, Seth Rogen

What's appealing here is the notion of fate, and that there are no accidents. Maybe the fetus Heigl and Rogen conceive by mistake was meant to be. Maybe these seeming opposites are soul mates. Maybe it's when we're at our least responsible that we are at our most intuitive. Tune in and decide for yourself. —Josh Robertson

Starring: Mila Kunis, Justin Timberlake

This movie embraces a view related to the thesis of When Harry Met Sally—only in this one, it would be that men and women can't have sex because the love thing gets in the way. Dylan (Timberlake) and Jamie (Kunis) try to do the FWB thing, but their emotions get the best of them. Are you in love? Say it. Say it! —Josh Robertson

Starring: Ellen Page, Michael Cera, Jason Bateman, Jennifer Garner

You may never look at Sunny D the same way, but Juno will always leave you feeling content. Watching a simultaneously lighthearted and heavy-hitting movie about a precocious teenage girl having a baby seems like a great way to deter any type of romance—however, Juno radiates indie sweetness, and that song by The Moldy Peaches always hits different. —Mallorie List

Starring: Kate Winslet, Jim Carrey

Joel (Carrey) is fighting a desperate battle within his head, trying to hold onto memories of his lover Clementine (Winslet) as they are being erased by a company he has hired to do the job. The movie is multilayered, multifaceted, and frankly very confusing, so we won't explain any more of the details. But suffice it to say that Joel is heroic in his desire to hold onto something he doesn't even understand, and such heroism inspires a spooky sort of romance. —Josh Robertson

Starring: Tom Cruise, Renee Zellweger

This movie is actually mostly about sports and our everyday struggle to earn a buck in this world without sacrificing our principles and dignity. But a romance between Cruise and Zellweger emerges, and the film's emotional climax is the scene in which he says, "You complete me," and she answers, "You had me at hello." That goes a long waiting in making viewers forget about all that male self-doubt. —Josh Robertson

Starring: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt

Kat Stratford invented spoken word poetry when she said “I hate you so much it makes me sick, it even makes me rhyme.” Cult classics like 10 Things I Hate About You are the crème de la crème of date night movies. That quintessential late ‘90s blend of teenage angst, dating, and irresistible bad boy Heath Ledger doing a song and dance on the football bleachers is the best way to guarantee an enjoyable and modern-Shakespearean night in. —Mallorie List

Starring: Anna Karina, Jean-Paul Belmondo, Jean-Claude Brialy

Sexual empowerment is a beautiful thing, particularly as practiced by Angela (Karina). When her boyfriend Emile (Brialy) makes it clear he does not want to have a baby with her, she gets with his friend Alfred (Belmondo). It's the story of a woman, unhindered by guilt or timidity (Angela is a stripper, by the way), using sex to get what she wants. —Josh Robertson

Starring: Jack Lemmon, Shirley MacClain, Fred MacMurray, Jack Kruschen

The Apartment is the perfect old-school flick for any low-key romantic occasion, as it’s equal parts goofy and sweet. Jack Lemmon plays a businessman who lends his apartment out to men and their mistresses, in an attempt to move up in rank at his job. His infatuation with a witty elevator girl (MacClain) and her complicated relationship with his boss (MacMurray) make for an enjoyable, topsy-turvy story in true ‘60s fashion. —Mallorie List 

Starring: Jude Law, Natalie Portman, Clive Owen, Julia Roberts

In this twisted relationship movie, four people keep coupling and uncoupling—all the while telling each other really mean, raw things. Brits Dan (Law) and Larry (Owen) keep trading Americans Alice (Portman) and Anna (Roberts) like they were baseball cards. There's deceit. And cheating. And marriage. And divorce. And a strip club. And an Internet chat room. And Julia Roberts talking about swallowing. This is for anyone looking for a movie that shows the good, the bad, and the ugly sides of love. —Josh Robertson

Starring: Patrick Swayze, Jennifer Grey

The allure of the bad boy who's not really a bad boy at all. Swayze's Johnny Castle character is working class, and a goy, but he's a talented dancer who wants to make something of himself. Daddy doesn't see it that way, though. The fact that Jennifer Grey's character is called "Baby" seals the deal—this is a classic case of daddy-won't-listen. At the very least, the film will make your date recall feelings of rebellion for its own sake. —Josh Robertson

Starring: Hugh Grant, Andie MacDowell

Carrie (MacDowell) has a one-night stand with Charles (Grant), and then sleeps with him again despite being engaged at the time. Bad, bad, bad girl! It is clear early on that these two must end up together, or risk being horrible people. It's OK to cheat if the person you cheat with turns out to be your true love, right? —Josh Robertson

Starring: Sean Astin, Josh Brolin, Corey Feldman

When in doubt, classic ‘80s movies will always be there for you and your boo. The Goonies is a universal crowd-pleaser that has both entertainment quality and just a smidge of cutesy romance, which makes for a nostalgic night of doing the Truffle Shuffle. Just don’t act surprised if you feel braces behind that goodnight kiss. —Mallorie List 

Starring: Tony Leung Chiu Wai, Maggie Cheung

In the Mood for Love, the masterpiece in director Wong Kar-Wai's impressive career, is one of the most beautiful movies ever made, and nothing has such an intoxicating effect as its beauty. The story is simple: Two couples move into the same building in Hong Kong circa 1962, and gradually the man and the woman discover that their partners are cheating on them with each other. (So maybe that isn't so simple).

From this smart starting place, Wong paints an aching picture of restraint. It's more about what the characters don't do, how they don't move, what they don't say, than anything else. Wong lets the repetition of certain musical motifs, the slow-motion sequences, costume changes, and gorgeous formal flourishes do more than any actor could. —Josh Robertson

Starring: Jeff Bridges, Rachel McAdams, James Franco, Mackenzie Foy

Though it’s not exactly romantic, The Little Prince is endearing enough to make you feel all warm and fuzzy inside while you’re snuggled up with your cutie. It may be an animated children’s movie meant to inspire, but watching it as an adult is just as effective at filling your heart to the brim—and watching it on date night is a foolproof way to weed out the bad apples who think they’re too good for kids films. —Mallorie List

Starring: Hugh Grant, Liam Neeson, Colin Firth, Laura Linney, Emma Thompson, Alan Rickman, Keira Knightley

This massive spiderweb of romantic comedy and drama has just about every flavor of human attraction known to man. If she swoons over a boy expressing his unrequited love, this film has that. If her fantasy is to be rescued by a knight in shining armor, this film has that. If she is touched by a widower dad who's looking to take a second chance, this film has that. Whatever sentiment she's looking for, Love Actually has got you covered. —Josh Robertson

Starring: Bill Murray, Scarlett Johansson

If your date night is more chaste than you were hoping for, maybe the fateful story of two strangers forming an unlikely bond in a foreign country will do the trick. Lost in Translation is a Sofia Coppola classic that proves how meaningful companionship can be when you click with someone, even if it’s superficially platonic. Though the film’s protagonists rely on each other for friendship, their chemistry exudes the feeling of unrequited love, and is the perfectly subtle way to drop a hint on date night. —Mallorie List

Starring: Jared Gilman, Kara Hayward

At the center of the film are two 12-year-old kids, a boy and a girl, who run away to a secluded beach where they camp out, sing, dance around in their underwear, and kiss. It transports viewers to a simpler time in their lives, a more innocent time, when they were just getting their first ideas about love. —Josh Robertson

Starring: Logan Lerman, Emma Watson, Ezra Miller

Coming-of-age stories may not always be the pick of the litter for date night, but The Perks of Being a Wallflower isn’t just any coming-of-age story. Deeper than your prototypical tales of navigating adolescence, this movie is a captivating look at the reality of stepping out of your comfort zone to grow up, fall in love and face your demons. It may be gut-wrenching at times, but it’s a moving film with sentimental moments that will leave you wanting to hug someone. Luckily, you’ll have someone on hand. —Mallorie List

Starring: Molly Ringwald, Andrew McCarthy, Jon Cryer

From the belly of the '80s comes a tale of class and broken high-school hearts. The popular and preppy Blane (McCarthy) develops feelings for Andie (Ringwald), but neither one fits into the other's world. Add Jon Cryer as Duckie, the goofy best friend who's secretly in love with Andie, and you've got a classic love triangle. —Josh Robertson

Starring: Julia Roberts, Richard Gere

The hooker with a heart of gold is a cliché, and really not of much concern to the viewers of this movie. Same goes for the rich handsome asshole corporate guy who gets in touch with his emotions, but we love it anyway. —Josh Robertson

Starring: Keira Knightley, Matthew Macfayden

What is the deal with Darcy (Macfayden)? He's rich, a bit gruff, and too aware of class differences, but then he changes when he decides it's Elizabeth (Knightley) he wants. Darcy has a hold on the popular female imagination in a way that's tough to understand. (Though he is kind of a badass...OK, we get). You aren't Darcy, but hopefully you'll do. —Josh Robertson

Starring: Adam Sandler, Emily Watson

Look, you're an average guy, right? Hell, for all we know you might even be described as "Sandler-esque." This is a movie about a guy, like you, who becomes a stud. In the beginning, Barry (Sandler) is angry at the world and helpless, partially because his seven abusive, manipulative sisters make his life a living hell. He gets in trouble with a phone-sex company that tries to extort money—we're not saying you'd ever do something like that, but we all know moments of weakness.

Yet, he's pursuing Lena (Watson), and she likes him. Their blossoming love brings out the best in Barry, who stands up to his sisters and the phone-sex company. Turns out there was a hero within Barry all along. And there is probably a hero within you—if your date is enough to draw it out of you. —Josh Robertson

Starring: Ione Skye, John Cusack

Since 1989, every girl has wanted the boom box moment: the moment when John Cusack stands outside Ione Skye's house blasting Peter Gabriel's "In Your Eyes" in a bid to prove how much she means to him. This half-baked idea—just standing there and letting a pop song do the talkin'—would not work in real life, but that's beside the point. —Josh Robertson

Starring: Michael Cera, Mary Elizabeth Winstead, Kieran Culkin, Aubrey Plaza

What’s more romantic than someone battling your evil exes for a chance to be your little thing? Scott Pilgrim vs. the World may be every recovered indie teen’s favorite movie, but we can’t really blame them; it’s the perfect example of director Edgar Wright’s signature modern camp. Combining romance, comedy, action, and well-timed comic book style animations, this movie is a surefire way to lighten your date night spirits. —Mallorie List

Starring: James Spader, Maggie Gyllenhaal

Of all the films in this list, Secretary might be the most potent. The tale of boss Edward (Spader) turning his mediocre new secretary Lee (Gyllenhaal) into a submissive BDSM partner is so perfectly told that it's caused many a woman to change her thinking about that sort of thing. It's like 50 Shades of Grey, but without being the fucking worst thing to ever take over the nation. —Josh Robertson

Starring: Tom Hanks, Meg Ryan

Like many romantic movies, this one has a clear finish line: A meeting between widower Sam (Hanks) and journalist Annie (Ryan) on the observation deck of the Empire State Building on Valentine's Day. The film tracks these two characters and the rendezvous, suggested by Annie on a whim, seems totally unlikely.

Will these two characters, who have never met in the film, somehow meet at the end? Of course they will. You can't make a movie about two people who have never met not meeting. That would be a terrible date movie. Ride it out. —Josh Robertson

Starring: Greg Kinnear, Jennifer Connelly, Nat Wolff, Lily Collins

Following the individual love lives of a separated middle-aged couple and both of their teenaged children, Stuck in Love is an underrated rom-com hit. The finely woven storylines of each family member’s journey through love also display the complexities of a modern family bond and might have you shedding a few tears by the end. But what would date night be without a little bit of crying? Boring, that’s what! —Mallorie List

Starring: Meg Ryan, Billy Crystal

This is the story of two people who think they're friends but end up realizing they ought to be lovers. The plot keeps referring back to a statement Harry (Crystal) makes early in the film: "Men and women can't be friends because the sex part always gets in the way." This is the oldest trick of logic in the book, but still makes for a great date movie. —Josh Robertson