9 Best Movies About Online Dating (And What to Learn From Them)

Like most people, I love movies. I have wonderful memories of seeing certain movies with my friends and family (“101 Dalmatians” for my first experience), and there are movies I’ll never get sick of (“Titanic,” for example). As Editor-in-Chief of DatingAdvice.com, online dating is also a big part of my life. Online dating is a big part of a lot of people’s lives as well, as 49 million have tried it.

Combining my knowledge of movies and online dating, today I’m bringing you nine films — from rom-coms to thrillers to documentaries — that showcase both the good and bad of online dating, and that can teach us a thing or two about finding love on the web.

This is the quintessential online dating movie, and I remember going to see it with my dad and sister when I was a kid. Released in 1998, “You’ve Got Mail” is set in New York City during the days of AOL (oh, that dial-up tone). Kathleen (played by ‘90s darling Meg Ryan) and Joe (played by everyone’s favorite dad Tom Hanks) meet in an over-30 chat room and set some rules when they start messaging: they won’t reveal their real names (just Shopgirl and NY152) or anything about their jobs, hobbies, friends, or family.

What they don’t know is Joe’s new bookstore franchise, Fox Books, is ruining business at Kathleen’s local bookstore, the Shop Around the Corner. It’s the classic tale of opposites attract and secret identities. It’s been over 20 years, so I think it’s OK to spoil the ending of this movie for those who haven’t seen it: Joe and Kathleen realize their feelings for each other, and the final scene shows them arranging a meeting with their online love interest at the park. Once they discover their identities, she says, “I wanted it to be you. I wanted it to be you so badly.” They kiss and live happily ever after with their giant laptops.

Lesson: Be upfront about who you are and what you want. There’s no point in getting to know someone online and then starting to feel something for them if you’re not going to be completely honest from the get-go.

“Must Love Dogs” is one of those comfort movies that I’ll watch with my mom and sister on rainy days, and it explores what online dating can be like for divorcees. It came out in 2005 and stars Diane Keaton as Sarah Nolan and John Cusack as Jake Anderson.

They’re both recently divorced, and their friends and family are eager to help them find someone new. Sarah’s sister is so eager that she creates a profile on a dating site without Sarah knowing, using her high school graduation photo as her main profile pic (she’s now 40), calling her voluptuous (she’s not), and telling potential matches that they must love dogs (an extra point for having the name of the movie said in the movie). Sarah decides to give into her sister and try online dating — going on a ton of awful first dates, including an accidental one with her own father.

Meanwhile, Jake’s friend shows him a printout of Sarah’s profile and tells him he’s already set up a date for the next day at the dog park. Sarah brings her brother’s dog, Mother Teresa, who she’s dog-sitting, and Jake brings his friend’s dog. They have some cute love/hate banter about Sarah’s profile where she indicates the man must love dogs, not must own a dog. There are some misunderstandings along the way, but it all ends well — with Sarah swimming across a lake to profess her feelings for Jake.

Lesson: Go ahead and create a dating profile on your own before your well-meaning, but nosy, sister does.

Not only is this a great mother-daughter movie, but it’s also a great online dating movie — because it shows the chaos that can ensue if someone else tries to take control of your love life. “Because I Said So” delves into the relationship between Milly (Mandy Moore) and Daphne, her mother (Diane Keaton).

Milly is the youngest of three sisters, and she’s also the worst at dating. It also doesn’t help that her mother is always interfering. This interference includes placing a personal ad on a dating site and screening all the men for her.

After Daphne meets Jason, who she thinks is perfect for Milly, they coordinate a “chance meeting” at Milly’s work. Soon after, they’re dating. Milly also starts dating another man, Johnny, who her mother met but didn’t like. As you probably guessed it, Milly finds out about her mother’s meddling and Jason’s knowledge of it. Plus, Johnny finds out she’s been seeing someone else. They all become estranged, but eventually Milly and her mom reconcile, and she sees that Johnny is who she’s meant to be with.

Lesson: Never, ever let your mom create your dating profile for you, especially if she’s controlling.

“Eurotrip” is one of the best teen movies of all time — not to mention it has one of the best songs to ever come out of a movie: “Scotty Doesn’t Know.” When Scotty’s girlfriend breaks up with him on graduation day, he gets drunk at a party to numb the pain. Before the party, though, Scotty is emailing with his German pen pal, Mieke, when his best friend, Cooper, tells him it’s weird that he talks to a foreign dude every day and that he’s probably a sexual predator.

Later, in a drunken haze, Scotty replies to Mieke’s email, in which he said he’d like to arrange a meeting. Scotty calls him a “sick German freak” and tells him he never wants to talk to him again. What he doesn’t realize is Mieke is a common German girl’s name. It’s too late to apologize to Mieke because she’s blocked his email, so he travels to Europe with Cooper and the twins, Jenny and Jamie.

From London to Paris to Amsterdam to Bratislava to Berlin and Rome, Scotty finally locates Mieke and explains everything. They have sex and promise to continue emailing, and then, on the first day of college, Scotty finds out Mieke applied to the same school to be with him.

Lesson: Make sure you fully understand the language you’re supposedly studying and using to communicate with a pretty girl overseas. Don’t listen to the dumbass friend in your group (we all have one) about dating, and don’t send angry emails when you’re drunk.

“Sex Drive” is a seriously underrated movie, in general, and it can teach us a lot about online dating, particularly in terms of honesty and safety. Ian, a recent high school grad, is pretending to be a stud online (when in reality, he’s shy, skinny, and a virgin) when he meets Ms. Tasty. They decide to get together in person, so Ian takes his brother’s beloved 1969 Pontiac GTO Judge, picks up his two best friends, Lance and Felicia, and makes the road trip from Chicago to Knoxville.

Along the way, the car breaks down, they have to deal with a sarcastic Amish man (a hilarious Seth Green), Felicia loses a tooth, and they end up in jail. Once they finally make it to the motel where Ms. Tasty is waiting, they find out her plan all along was to steal the car and sell the parts for cash. The rest involves a gun and a taco costume (you just have to see it). But the bad guys get arrested, the good guys are still alive, and Ian and Felicia discover how they feel about each other.

Lesson: Make sure the person you’re talking to online is who they say they are. Google them, run reverse image searches, and ask a lot of questions.

“Napoleon Dynamite” is a 2004 classic, and while the main focus is on Napoleon, some of the best scenes and lines come from his older brother, Kip. He’s 32, he doesn’t have a job, and he spends all day online talking to “babes.” Kip has one special babe, though, and that’s LaFawnduh.

To make some money and visit her in Detroit (he’s in Preston, Idaho), Kip goes in on a get-rich-quick scheme with Uncle Rico. LaFawnduh ends up coming to Preston, and spending the next few days falling even more in love. At the end of the movie, they both get on a bus and head back to Michigan. During the credits, the movie shows Kip and LaFawnduh getting married and riding a “wild honeymoon stallion” across a field together.

Lesson: If you meet someone online, have gotten to know them, and start to really like and trust them, don’t wait around — make it happen and meet in real life as soon as possible.

Before “Catfish” the TV show, there was “Catfish” the documentary. This is the only movie on our list that is based on a true story. Nev is a photographer living in New York City, and one day he receives a painting of one of his photos from 8-year-old Abby, who’s somewhat of a child prodigy. They friend each other on Facebook, and Abby starts telling Nev about her life and family, including her mom, stepdad, and older half-sister named Megan.

Nev and Megan start messaging each other, and Nev’s brother Ariel decides to document their online relationship as it progresses. The brothers soon discover holes in Megan’s story — such as the song covers she’d been sending Nev (implying that it’s her singing) were actually taken from YouTube. Nev and Ariel travel to Michigan to confront Megan, but it’s Angela who answers the door.

Turns out, Angela had about 15 fake profiles, including Megan and Abby’s, and she said her correspondence with Nev had reignited her passion for painting. There were other lies, but Nev forgives her and uses this as an opportunity to help other people going through similar situations. Today, Angela has a website to promote her paintings, and she and Nev are still Facebook friends.

Lesson: Be careful about falling too easily and too quickly online, and don’t wait too long to connect with an online match in person.

“Hard Candy” is probably the most disturbing movie on this list, and it flips the typical girl-meets-predator-online story on its head. Hayley, 14, and Jeff, 32, are having a very sexual conversation online and agree to meet up at a coffeehouse. They go back to Jeff’s house, where Hayley puts something in his drink to make him pass out.

When he wakes up, he’s tied to a chair, and she admits that she’s been watching him and knows he had a part in the rape and murder of a local girl who’d gone missing. As Hayley threatens him with a gun, a stun gun, castration, and a noose, Jeff continues to deny any involvement. It all culminates with Jeff’s confession and forced suicide on the roof of his house.

Lesson: This one is pretty easy. While Hayley is a crazy vigilante with an awesome name, Jeff is pure evil. Don’t be an evil person, like Jeff, and don’t do sketchy shit online or offline because someone can always find out. You never know who will want to serve you up some justice.

Not to be confused with the Miley Cyrus movie, “LOL” is a 2006 indie flick starring Greta Gerwig. Through the stories of three college graduates Tim, Chris, and Alex, “LOL” examines the often unhealthy relationship people have with technology.

Tim can’t take his eyes off his laptop, even as he’s making out with his beautiful girlfriend. Chris only conducts his relationships through his cellphone. And Alex’s obsession with chat rooms ruins a potential real-life relationship.

Lesson: Online dating addiction and technology addiction, in general, is real, so pace yourself. Don’t stop living in the real world, neglecting your family, friends, career, health, and hobbies.

Over the years, I’ve learned that movies provide more than just a good laugh, cry, or scare — they sometimes also provide tips that we can implement in our own lives. Next time you’re watching a new movie or rewatching one of your favorites (whether it’s about online dating or not), pay attention to the lessons that are being shared. You just might find something worthwhile!