5 Best Movies About Online Dating

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Dating is hard, and online dating is even harder. In this modern age, it's getting increasingly harder to meet somebody organically, so people find themselves signing up for apps like Tinder, Hinge, or Bumble (and these are just the mainstream ones). At a certain point, the whole thing feels like you're shopping on some big-box site for a spouse, and while plenty of people successfully find relationships through dating apps or websites, the fact that it's the norm in the dating world now can feel sort of overwhelming. So how is this phenomenon represented in pop culture ... or more specifically, in movies?

There are, actually, a decent number of movies that focus on online dating ... and they cover the good and bad outcomes. (Some of the outcomes, it should be said, aren't just bad — they're actively deadly.) These picks run the gamut; some might have you feeling hopeful about meeting your soulmate online, and some might have you considering a life of solitude or, perhaps, a monastery. From a classic early entry into this niche rom-com genre from Nora Ephron to two modern horror stories about what happens when online dating goes wrong, here are five great movies about online dating.

• Cast: Tom Hanks, Meg Ryan, Parker Posey, Greg Kinnear
• Director: Nora Ephron
• Rating: PG
• Runtime: 119 minutes
• Where to watch: VOD

Nora Ephron's 1998 romantic comedy "You've Got Mail" marks the third on-screen relationship between stars Tom Hanks and Meg Ryan in this particular cinematic era — they shared the screen previously in 1990's "Joe Versus the Volcano" and in 1993's "Sleepless in Seattle," the latter of which was also directed by Ephron — and it's also one of the defining movies about online dating. The conflict in "You've Got Mail" is actually professional; while Ryan's Kathleen Kelly operates an independent bookstore filled with children's literature, she finds herself battling the creep of major corporate bookstores in her New York neighborhood (the Upper West Side), specifically. That's where Hanks' Joe Fox, who works for Fox Books, a major bookstore chain in the style of Borders or Barnes & Noble.

It is, admittedly, pretty funny that physical bookstores are at the center of "You've Got Mail" considering that, like meeting in person, those have largely fallen by the wayside now that you can order books online. (You should still support local bookstores, though.) So what about the online dating aspect? Despite being with other romantic partners — Kathleen is dating political columnist Frank Navalsky (Greg Kinnear), and Joe is involved with publish Patricia Eden (Parker Posey) — Joe and Kathleen have been quietly chatting over AOL for some time, and they strike up a genuine connection. Many elements of "You've Got Mail" are a bit outdated, but it's basically the blueprint for online dating movies.

• Cast: Sebastian Stan, Daisy Edgar-Jones, Charlotte Le Bon
• Director: Mimi Cave
• Rating: R
• Runtime: 114 minutes
• Where to watch: Hulu

Penned by Lauryn Kahn and helmed by "Poker Face" and "Holland" director Mimi Cave, the 2022 horror thriller "Fresh" is actually a movie where the protagonist, Noa (Daisy Edgar-Jones), tires of online dating and tries to meet somebody in the wild ... with very mixed results, to say the least. After she has trouble finding love through an app, Noa meets a guy at a supermarket who says his name is Steve (Sebastian Stan), and they form an immediate connection. The two start dating, and before long, Steve invites Noa to join him for a weekend getaway at a remote cabin, which is where "Fresh" really takes several bizarre twists and turns.

If you're at all familiar with the plot of "Fresh," you know that this film involves some straight-up cannibalism, but we'll let you be surprised about how and why that even comes up. (We'll give you a hint: Steve is not Steve's real name, which is the first of many things he's hiding.) If you, like Noa, are growing tired with online dating, a movie like "Fresh" might actually encourage you to give the apps another shot.

• Cast: John Cusack, Diane Lane, Stockard Channing, Christopher Plummer
• Director: Gary David Goldberg
• Rating: PG-13
• Runtime: 98 minutes
• Where to watch: The Roku Channel, VOD

Whether you're dating online or going to bars to find prospects, you want to make sure you share some vital things in common with a would-be partner ... like, maybe, that you both love dogs? Gary David Goldberg's 2005 romantic comedy "Must Love Dogs" isn't just about online dating, but also finding someone who's going to fit perfectly into the life you've already built. When we first meet Sarah Nolan (Diane Lane), she's middle-aged, divorced, and loves her job as a preschool teacher; still, her friends and family want her to get back out there and start dating again. With their encouragement, she signs up for a website called Perfect Match that might help her find her soulmate — and unbeknownst to Sarah, another recently divorced singleton, Jake Anderson (John Cusack), is actively being encouraged to go out and meet women. (Jake tries to get out of this due to his obsession with making boats, which ... is pretty flimsy, as far as excuses go.)

To say that Jake and Sarah's first meeting doesn't go well is a bit of an understatement — trying to impress her while she dogsits for a friend's Newfoundland, he goes to a dog park with a terrier he borrowed from somebody else and unsuccessfully passes it off as his own pup — but ultimately, Jake and Sarah realize they might have a pretty strong connection. "Must Love Dogs" is cheesy and corny, but it's also really sweet — and the dogs are very cute. 

• Cast: Meghann Fahy, Brandon Sklenar, Violett Beane, Jeffery Self
• Director: Christopher Landon
• Rating: PG-13
• Runtime: 95 minutes
• Where to watch: Amazon Prime Video

During Season 2 of "The White Lotus," Meghann Fahy handily proved that she's one of the most exciting actresses of her generation — and with starring roles in deeply fun projects like "Drop," this talented performer is keeping audiences fully entertained. The funny thing about "Drop," a movie that casts Fahy as widow, single mom, and successful therapist Violet Gates, is it's not really about online dating foibles ... but, more specifically, what can happen during an online date that can derail everything.

Obviously, the scenario in "Drop" is completely heightened and even patently absurd, but that's what makes this movie so fun. When Violet meets up with her online date, photographer Henry Campbell (Brandon Sklenar), at a high-end bar and restaurant atop a skyscraper, everything seems to be going normally until Violet starts getting strange text messages with specific instructions. As the texts keep rolling in, they tell her that she must steal an SD card from Henry's camera and threaten her son's safety if she doesn't comply; all the while, Violet tries to keep her cool, wondering if Henry or another patron lurking in the restaurant is responsible for these threatening texts. "Drop" is really silly, incredibly entertaining, absurdly fun, and a great showcase for Fahy and Sklenar — even if nothing like this would probably ever happen in any version of reality.

• Cast: Miles Teller, Lio Tipton, Jessica Szohr, Scott Mescudi
• Director: Max Nichols
• Rating: R
• Runtime: 86 minutes
• Where to watch: Tubi, VOD

When we first meet Lio Tipton's ("Crazy, Stupid, Love") Megan in the 2014 romantic comedy "Two Night Stand," she's unemployed, violently single, and surrounded by roommates who are borderline desperate for her to either get a job or move out entirely. Undaunted by all of this, Megan joins a dating app and matches with a guy named Alec ("Top Gun: Maverick" star Miles Teller), and after she gets dragged out to a nightclub with some girlfriends and runs into her ex-boyfriend, she hits Alec up and decides she wants to "use" him, so to speak, as a one-night stand.

This does not go according to plan when, the next morning, Megan wakes up at Alec's house to discover that the city has been hit by a massive blizzard — trapping both of them inside. Stuck together, Alec and Megan end up bonding, despite the fact that Alec's ex-girlfriend Daisy ("Gossip Girl" veteran Jessica Szohr) is still very much on his mind, something that makes Megan understandably upset. "Two Night Stand" is a cute, fun movie with two unbelievably charismatic stars, plenty of wacky misunderstandings, and a solid premise that forces the two protagonists together. It's also, honestly, a public service announcement about hitting up dating apps if there's a blizzard in the weather forecast.