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The Dos and Don’ts of Flirting and Falling in Love, According to Movies

Movies have taught us a lot about flirting, dates, love, lust, and romance. Some people believe romantic movies ruin our expectations of falling and staying in love here in the real world, but 2014 research by the University of Rochester says watching rom-coms can actually help couples master relationship skills and cut divorce rates.

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So what if mushy movies have given your crush great expectations on how you’ll act? At least you can learn how they want to be wooed (i.e. a surprise rendition of “Can’t Take My Eyes Off Of You” on the bleachers).

Will the Casablanca pick-up line, “Was that cannon fire, or is my heart pounding?” work on every random crush in a bar? Probably not, but here is the ultimate do’s and don’t of datings from movies that can teach us how to successful woo someone and fall in love.

We analyzed 33 movies for the best and worst advice on how to flirt and fall in love. Our advice from films like Pretty Woman, Say Anything, You’ve Got Mail, and more.


1. Master the art of your come-hither look and rely on glances as much as words. Learn from the best: Mickey Rourke in the scintillating flick 9 1/2 Weeks. These looks are powerful, people.

2. Get their attention. Combine a coy smile with diligent and charming pursuit a la Ryan Gosling in The Notebook. Getting their attention also means keeping it by being playful and persistent. When a person shows up frequently in your life, it feels like you’re meant to be together. Your crush also wants to know they’re worth the chase. Be proactive (not necessarily hanging from a Ferris wheel), because a lazy guy is beyond unattractive.

3. Fall for your best friend. The 2002 movie Brown Sugar taught us that long, enduring relationships are born first from friendships and to be actively involved in your crush’s career development and success.

Dirty Dancing - Lover Boy Scene

4. Teach them a new skill. Flex your expertise and show your crush how to throw a baseball, bowl, or, in the case of Patrick Swayze, dance. Dirty Dancing showed us that a man with talent is hot, especially if he has the patience to teach with a soft but strong hand.

5. Bring flowers. Send flowers. The point is: flowers. Copy Matthew McConaughey in How to Lose a Guy in 10 Days and have a bouquet sent to their work. Flowers are always surprising, always wanted, and will make you stand out from the pack. One tip: Don’t send red roses, that’s too intense.

6. Never stop dating and never stop coming up with inventive dates, much like Adam Sandler in 50 First Dates. Moreover, plan dates without the expectation of getting anything in return except their company.

7. Always bring candy, especially if you know their favorite brand. Mark Ruffalo and Jennifer Garner sucking on Razzles in 13 Going on 30 while swinging is the cutest, they-have-to-be-together date. Take notes.

8. Show your kindness. Having a short fuse or being mean to strangers during a date is a surefire way to appear unattractive or beastly if you will. There’s a reason Belle didn’t like the Beast when they first met and it wasn’t because of his hair. Beauty and the Beast teaches us that if you show your real, kind personality even a mane of back hair is handsome.

9. Be a handyman. When Johnny Depp fixes that door in the drama/romance Chocolat, he not only bonds with his crush but shows how hands-on and useful he is in small everyday chores. That. Is. Sexy. Plus, once you lend a hand, you usually get a sweet treat in return.

10 Things I Hate About You: Can't Take My Eyes Off You (Heath Ledger)

10. Sing them a song (especially if you’re bad at singing). Surprise your crush with a song in an untraditional location. This is one of those big, bold moves you almost only see in the movies, which makes it all the more powerful in real life. Take cues from Say Anything, The Wedding Singer, and 10 Things I Hate About You.

11. Whisper. Remember that final whisper between Bill Murray and Scarlett Johansson in Lost in Translation? While their romance was platonic, there was nonetheless a deep, meaningful connection between the two, sealed tighter by the exchange of a few words only they know. Keep some things between the two of you.

12. Let the tension build. When strangers Clark Gable and Claudette Colbert are forced to share a room in It Happened One Night, so ensues an adorable, semi-cheeky scene of them changing behind sheets to maintain modesty in such close, intimate quarters. This restraint boosts their passion, so hold back until you both can’t stand it anymore.

13. Believe in their ability to be more than their upbringing. We look for love in people who see something greater for ourselves. In Bonnie and Clyde, Clyde takes Bonnie away from her Depression-era life and she falls in love with him because he believes she deserves bigger. The lesson: Show your crush that you see their potential. But refrain from robbing banks.

14. Date with a young heart and keep dating as you get old and wrinkly. i.e. Meryl Street and Clint Eastwood in The Bridges of Madison County. Love and flirtation do not have an age limit.

Gone With The Wind - Kiss

15. Kiss like Clark Gable and Vivien Leigh in Gone With the Wind. Vintage film kisses are the best; full of passion and embrace. Lose the tongue, dude.

16. Make an effort to bond with their parents, even if they hate you at first. Big nod to Kumail Nanjiani from The Big Sick.

17. Pass notes. Romeo + Juliet got a lot wrong when it comes to romance (don’t pretend to kill yourself to scorn your parents), but what they got right was the practice of passing secret notes. Keep the messages short, honest, and rely on the literary experts if you need the right words.

18. Be a bit unreachable. In other words, flee to the mansion castle like Edward Scissorhands. To an extent, it helps when your crush has to do some chasing as well. Once you become temporarily unreachable, it will prompt them to meet you half way.

19. Remember relationships and people are a little f***ed up. Eternal Sunshine of the Spotless Mind taught us the important lesson that relationships come with ups and downs, and there’s no use trying to avoid them. Also, to remain unique and not try to change the other person or yourself to become one singular entity. Let people have their problems.


1. Don’t catfish your crush via email like Tom Hanks in You’ve Got Mail.

2. Don’t ask your crush to attend your wedding if you still have feelings for them. Ahem, My Best Friend’s Wedding.

3. Don’t force them to dinner with your parents (via kidnapping) or do anything Vincent Gallo does in Buffalo ‘66.

4. Don’t pretend to be the opposite sex to get “in” with your crush like they do in Some Like it Hot and Tootsie.

5. Don’t mislead them into thinking you’re a millionaire as Charlie Chaplin does in City Lights, even if it is by accident.

6. Don’t bond over negatives as in the Silver Linings Playbook. Sure, liking the same Netflix shows is a plus but pursuing someone because you both are depressed does not a healthy relationship make.

The Graduate (1967) - "Mrs. Robinson, you're trying to seduce me. Aren't you?"

7. Don’t seduce someone a lot younger like Mrs. Robinson in The Graduate. It’s just icky. It doesn’t matter if the older party is man or woman, there’s an inherent power discrepancy in play that is not OK. Another example of this would be Lolita  which if you know the story is a big, fat don’t.

8. Don’t bribe your crush with money like Richard Gere in Pretty Woman.

9. Don’t harass your secretary or try to date anyone from work like James Spader in Secretary or Eddie Murphy in Boomerang. Some may think it’s hot, but air on the side of respect and wait until a nice date to pull out the spanking tools.

10. No offense, but don’t offer to wait in the freezing water if both of you can fit or take shifts on the plank of wood. Share the door, Rose! Titanic.

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Jahla Seppanen
Former Digital Trends Contributor
Born and raised off-the-grid in New Mexico, Jahla Seppanen is currently a sports, fitness, spirits, and culture writer in…
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