The Best Movie Date Scenes, From The Romantic To The Tragic

Dating might as well be a sport. Sometimes it makes you feel like a real winner. Sometimes you score. Other times, you wind up hurt and swear that you'll never get back out on the court again. Anyone who has done the whole dinner-and-a-movie thing knows that dating is rarely comfortable or easy — even if it's totally worth the potential awkwardness should things actually work out.

Fortunately, you don't have to start swiping on Tinder to experience dating life. Instead, let these beloved movie characters experience the ups and downs for you. I've curated a list of the greatest date scenes from movies, so that you can sit back, relax, and not ask a person "So, what do you do?" for the 10th time this month.

Some of these dates are super romantic and may make the more emotional among us tear up. Other scenes? Well, you may just cringe with second-hand awkwardness.
Advertisement
1 of 36
BEST: When Harry Met Sally (1989)

Technically more of a friend-date than a date-date, but come on, who are we kidding with these two? Sally's (Meg Ryan) orgasmic lunch performance can never be forgotten.
2 of 36
WORST: Legally Blonde (2001)

Getting dumped sucks. Getting dumped when you think your boyfriend is about to propose? Well, that's a whole other level of suck. Alas, it's not all bad: without this heinously bad date, Elle would have never gotten that law degree.
Advertisement
3 of 36
BEST: The Notebook (2004)

An abandoned house may not make the best date location, but Allie (Rachel McAdams) and Noah (Ryan Gosling) don't need a candlelit dinner to ignite their chemistry.
4 of 36
BEST: Titanic (1997)

"So... you wanna go to a real party?" Yes, Jack. With you, any day.
5 of 36
BEST: 10 Things I Hate About You (1999)

Kat (Julia Stiles) and Patrick (Heath Ledger) are pretty much always at each other's throats (you know, in a "we're-secretly-in-love" way) so having their first kiss on a paintball field seems very appropriate.
6 of 36
WORST: Knocked Up (2007)

A date that starts with Ben (Seth Rogen) raving about Vince Vaughn and ends with Alison (Katharine Heigl) telling Ben she's pregnant isn't... ideal.
7 of 36
WORST: Hitch (2005)

A food tasting sounds seriously romantic... until Hitch's (Will Smith) peanut allergy turns half his face into a swollen nightmare.
Advertisement
8 of 36
BEST: A Walk To Remember (2002)

Landon (Shane West) naming a star after astronomy-loving Jamie (Mandy Moore) has set a very high bar for significant others.
9 of 36
WORST: Clueless (1995)

During her "first date" with Christian (Justin Walker), Cher (Alicia Silverstone) literally throws herself off the bed in a failed attempt at seduction. Alas, their love was never meant to be: Christian just isn't into girls.
10 of 36
WORST: Along Came Polly (2004)

Reuben (Ben Stiller) wants to impress the free-spirited Polly (Jennifer Aniston) by following through on her request to eat at an authentic Moroccan restaurant. Unfortunately, Reuben's IBS has other plans for the night.
11 of 36
WORST: Back To The Future (1985)

Here's one bad date that you can't replicate. When Marty (Michael J. Fox) realizes he's at risk of messing up his timeline forever, he agrees to go on a date with his own mother (Lea Thompson) in order to repair it. Alas, fighting off his mom's advances is trickier than expected... and the whole thing is just seriously icky.
12 of 36
WORST: 40 Year-Old Virgin (2005)

Things quickly turn sour for Andy (Steve Carrell) when he realizes his date (Leslie Mann) is a drunk-driving nightmare in a newsboy cap.
Advertisement
13 of 36
BEST: Lady & The Tramp (1955)

First dates are always best when they come with a big plate of carbs, and sharing food has never seemed sweeter than in this iconic Disney flick.
14 of 36
BEST: Going The Distance (2010)

Bad wine is better when you're with someone you like.
15 of 36
BEST: The Lizzie McGuire Movie (2003)

Paulo (Yani Gellman) is a jerk (not to mention a terrible singer) but you have to admit that this guy knows how to plan a good date. I mean, a Vespa tour of Rome? No wonder Lizzie (Hilary Duff) was so smitten.
16 of 36
WORST: Trainwreck (2015)

Amy (Amy Schumer) and Steven's (John Cena) nice night at the movies is ruined when a guy calls Steven "Mark Wahlberg." It doesn't exactly calm Steven down when Amy comes back from a bathroom break stoned.
17 of 36
BEST: No Strings Attached (2011)

The date between "friends with benefits" Emma (Natalie Portman) and Adam (Ashton Kutcher) starts Adam presenting Emma a bouquet of carrots, sharing milkshakes, and hitting the LACMA. Unfortunately, it ends with loads of commitment issues, and Emma fighting Adam "like a hamster."
Advertisement
18 of 36
BEST: Aladdin (1992)

Cruising around the world on a magic carpet is like the elevated version of the high school drive-around.
19 of 36
WORST: American Psycho (2000)

The second Reese Witherspoon breakup on this list. Patrick (Christian Bale) doesn't exactly spare fiancée Evelyn's (Witherspoon) feelings when he tells her she's just not that "important" to him. Let's be real though: Evelyn totally dodged a bullet, given her boyfriend's psycho killer tendencies.
20 of 36
WORST: The Break-Up (2006)

Not sure what's worse: An accountant who refers to his job as "the biz," or one who tries to seduce you with apple martinis. Brooke (Jennifer Aniston) gets the whole package. Thank God for the fake phone call trick.
21 of 36
WORST: How To Lose A Guy In 10 Days (2003)

Andi (Kate Hudson) goes from "cool girl" to "psychotic girlfriend" in the name of research. That research includes sobbing at a restaurant because her date Ben (Matthew McConaughey) thinks she's "fat." At least they're both playing one another: Ben, an ad man, is trying to woo her in order to score a big diamond account.
22 of 36
BEST: Crazy, Stupid Love (2011)

Before they were falling in love in a "City of Stars," the La La Land co-stars had a wonderfully romantic night that was supposed to be a one-night stand.
Advertisement
23 of 36
BEST: Braveheart (1995)

This romantic horseback ride through the mountains of Scotland makes up for the movie's violent bummer of an ending.
24 of 36
BEST: Harry Potter and the Goblet of Fire (2005)

Sure, Hermione (Emma Watson) wasn't exactly in love with Viktor Krum (Stanislav Ianevski) when he escorted her to the ball, but that doesn't make this a bad date. Hermione's look was fire and her date was hot, a great dancer, and a star Quidditch player. Plus, the Yule ball made Ron (Rupert Grint), the boy she would go on to marry, realize how stupid he was for not seeing Hermione in "that way."
25 of 36
WORST: Silver Linings Playbook (2012)

This is why you don't patronize your dates. Maybe if Pat (Bradley Cooper) kept his mouth shut about how "crazy" Tiffany (Jennifer Lawrence) was, they would have been dancing a lot earlier in the movie.
26 of 36
BEST: Notting Hill (1999)

"For June who loved this garden, from Joseph who always sat beside her." BRB, already crying over this budding relationship.
27 of 36
BEST: Love & Basketball (2000)

The only thing Monica (Sanaa Lathan) and Q (Omar Epps) love more than the game... is each other.
Advertisement
28 of 36
BEST: The Ugly Truth (2009)

Dinner, drinks, dancing — PLUS elevator an elevator hookup? These co-workers know how to have fun on a business trip.
29 of 36
BEST: Twilight (2008)

Usually, dates in which your new beau orders nothing because he's on a "special diet" would be a dud. Here, Edward (Robert Pattinson) doesn't need to eat: He's getting his fill on smoldering eye contact with Bella (Kristen Stewart).
30 of 36
BEST: 13 Going On 30 (2004)

Who knew all you needed for the perfect date was Razzles, a walk along the Hudson, and a swing set? Of course, Mark Ruffalo doesn't hurt, either.
31 of 36
WORST: Carrie (1976)

Umm, because a fiery, bloody massacre brought on by your telekinetic date is soooo not how you imagined your after prom going down.
32 of 36
BEST: Pitch Perfect (2012)

If you're an '80s obsessive, then Becca (Anna Kendrick) and Jesse's (Skylar Astin) low-key dorm date is one of your dreams... even if it ends kind of weird.
Advertisement
33 of 36
BEST: 500 Days of Summer (2009)

500 Days of Summer may not be a "love story," as the narrator insists, but playing house in IKEA is certainly a lovely date. (Ironically, going to IKEA for any other reason can possibly ruin your relationship forever.)
34 of 36
BEST: The Little Mermaid (1989)

Sure, we could have done without all of the sea creatures acting as unified wingmen, but isn't Prince Eric dreamy? And who doesn't love a boat ride when you're not obligated to row? Just saying.
35 of 36
BEST: Fifty Shades of Grey (2015)

You don't have to be into BDSM to appreciate Christian's (Jamie Dornan) thrilling date idea: a private plane ride.
36 of 36
Like this post? There's more. Get tons of celebrity news, fun takes on pop culture, and trending stories on the Refinery29 Entertainment Facebook page. Like us on Facebook — we'll see you there!
Advertisement

More from Pop Culture

Watch

R29 Original Series