1. When Harry Met Sally
Nora Ephron wrote a perfect screenplay—this is not up for debate—that at its heart asks, "Can men and women ever really be friends?" In the case of Harry and Sally, the answer is yes, they can be. Friends and soulmates.
2. Enough Said
Eva (Julia Louis-Dreyfus) starts dating Albert (James Gandolfini), and when she realizes one of her massage clients (Catherine Keener) is Albert's ex-wife, she doesn't tell either of them about the connection. Instead, she fishes around for information and hilarity (and heartbreak) ensues.
3. Jerry Maguire
"Show me the money." "You had me at hello." "Did you know the human head weighs eight pounds?" It's no coincidence everyone you know can quote at least one (and probably all three) of these Jerry Maguire lines. The Tom Cruise/Renée Zellweger/Cuba Gooding, Jr. vehicle—about a sports agent who gets a conscience—is the kind of movie that worms its way into your brain and stay there for years to come.
4. Love & Basketball
This is more of a sports-rom than a rom-com, but it's a love story for the ages regardless. The movie follows Monica and Quincy as they go from ball-playing kids to ball-playing teens to ball-playing lovers to ball-playing exes to "Play me." "For what?" "Your heart." Epic.
5. Never Been Kissed
There are so many Drew Barrymore movies to choose from! In this one, she plays a copy-editor who goes back to high-school undercover for a big-break story—and falls in love with a teacher in the process. The movie makes the list for many reasons: the wardrobe, the Shakespeare references, the existence of Molly Shonnon. Above all, it makes the list for bringing a character called Josie Grossy into our lives.
6. Pretty Woman
If you think about the plot for too long—sex worker falls in love with arrogant rich man—it can start to feel icky. So don't do that! Just enjoy it for what it is: an iconic movie that showcases the uncanny charm of one Julia Roberts.
7. My Best Friend's Wedding
Julia Roberts and Dermot Mulroney play best friends who made a pact to marry each other if they didn't find the love by 28 (lol, yes, 28). With her birthday fast approaching, he announces an unexpected engagement—and she realizes she's in love with him and must sabotage the wedding. Spoiler-ish alert: It doesn't end the way you think it would.
8. There's Something About Mary
Cameron Diaz plays the title character, a woman who has an incredible effect on the men in her life—all of whom are (pretty inappropriately) competing with each other for her attention. It's brought to you by the Farrelly Brothers, the guys who did Dumb & Dumber, which is why you'll recall some truly batshit scenes, like the one where Mary puts ~ejaculate~ in her hair thinking it's gel.
9. Sleepless In Seattle
Another Nora Ephron classic (co-written and directed by her). The story follows a widower named Sam (Tom Hanks) who calls into a radio show to discuss his heartbreak and attracts the attention of countless female listeners. Among them is a woman named Annie (Meg Ryan), who's engaged to be married but feels like something is missing in her relationship. With a little scheming by Sam's son, Sam and Annie eventually meet at the top of the Empire State Building.
10. Bridget Jones's Diary
We've all been Bridget Jones at one point in our life: single, fretting over men, and utterly disgusted by the thought of working out. Renée Zellweger brings the character to life perfectly, and Hugh Grant and Colin Firth as her love interest are not too shabby themselves.
11. Obvious Child
The premise of this movie doesn't sound comedic—young woman has an abortion after a one-night stand leaves her pregnant—but writer-director Gillian Robespierre's hilarious script brings a lot of light to a plot that could easily end up feeling dark. It helps that Jenny Slate is perfect as Donna, a hapless comedian/bookstore clerk who has some very relatable thoughts on what women's underwear looks like at the end of the day.
12. Before Sunrise
Richard Linklater's iconic tale of Jesse and Celine isn't *technically* a comedy, but it certainly delivers in the romance department. After meeting on a train in Europe, Jesse and Celine spend all night walking and talking in Vienna. They part ways at the end of the movie, but fear not—their story continues in the sequels Before Sunrise and Before Midnight.
13. 10 Things I Hate About You
There have been countless movie adaptations of Shakespeare over the years, but this 1999 classic remains the platonic ideal of Shakespeare adaptations. This one has everything—a fantastic cast (Julia Stiles, Heath Ledger, Gabrielle Union, Joseph Gordon-Levitt), an amazingly '90s soundtrack (Letters to Cleo, Save Ferris, the Cardigans), and what must be the only successful attempt in cinematic history to make paintball look romantic.
14. Knocked Up
Like Obvious Child, Knocked Up tells the story of a woman who finds herself pregnant after a one-night stand, only in this one, she decides to keep the baby. At first Alison (Katherine Heigl) and Ben (Seth Rogen) don't seem to work, but by the end of the movie, you'll be sold.
Clueless isn't the first movie the comes to mind when you think of "classic rom-coms," but there's no question that it has deep roots in the genre. Jane Austen, author of Emma (on which the movie is based), was the original rom-com queen. Even if you feel a little odd about the fact Cher—spoiler alert—ends up with her ex-stepbrother Josh, you can't deny that young Paul Rudd is a treasure.
16. A Lot Like Love
In this underrated gem, Oliver (Ashton Kutcher) and Emily (Amanda Peet) go from friends with occasional benefits to just friends to lovers over the course of several years. These kinds of relationships rarely work out in real life, which is one reason they're so fun to watch on screen.
17. Just Friends
Most people don't carry flames for their high-school classmates for 10 years, but most people don't look like Ryan Reynolds and Amy Smart. Ryan plays Chris, a former nerd who returns to his hometown to find himself still struggling with feelings for Jamie (Amy Smart), the woman who didn't return his sentiments in his younger days. Also recommended if you're still pining for Chris Klein's glory days—he plays the other guy competing for Jamie's affection.
18. Away We Go
When Verona (Maya Rudolph) and Burt (John Krasinski) find out that they're expecting a child, they can't decide where to raise it. Their solution? Visit friends and family all over the country to see what might suit their new family. Come for Verona and Burt's quirky and sweet relationship, stay for an incredible supporting cast that includes Allison Janney, Maggie Gyllenhaal, Carmen Ejogo, and Catherine O'Hara.
19. Along Came Polly
A lot of Jennifer Aniston movies get a bad rap, but this one is a gift. Jen plays Polly, a long-lost middle-school classmate of Reuben (Ben Stiller), a buttoned-up insurance underwriter. The pair start dating after Reuben's acrimonious split from his wife (Debra Messing), and free-spirited Polly shows Reuben how to live a little.
20. You've Got Mail
That "you've got mail" voice may have gone the way of the 56K modem, but this second Meg Ryan and Tom Hanks team-up remains eternal. She wanted it to be him! She wanted it to be him so badly!
21. Waiting To Exhale
Based on the novel of the same name by Terry McMillan, Waiting To Exhale was lauded for featuring an all-African-American cast led by Whitney Houston, Angela Bassett, Lela Rochon, and the great Loretta Devine. When their lives are rocked by the men in them, the four women realize the power of their friendship (and the power of fire, which is nice if you want to burn your soon-to-be-ex's things). Fun fact: Waiting to Exhale was directed by Forest Whitaker, who also directed Whitney in the "Exhale (Shoop Shoop)" music video.
22. The Cutting Edge
What happens when you pair a recently retired hockey player with a figure skating star who's spoiled AF? A dream team that actually might have a shot at gold at the 1992 Winter Olympics. No, really.
The king of rom-coms Garry Marshall directed real-life lovebirds Goldie Hawn and Kurt Russell in this sweet movie about an obnoxious heiress who falls off her yacht (hence the title) and quite literally into the arms of the local carpenter (Kurt) while suffering from a bad case of amnesia.
24. Look Who's Talking?
What's cuter than a talking baby voiced by Bruce Willis? Watching Kirstie Alley and John Travolta figure out how to take care of said baby in a sweet, sweet film from Amy Heckerling in her pre-Clueless days. The sequels, Look Who's Talking Too (directed by Heckerling) and Look Who's Talking Now (produced by Heckerling) are also great fun.
25. The Break-Up
If you break up with someone, do not continue to live with them, no matter what, otherwise you will end up like this movie, basically. Jennifer Aniston and Vince Vaughn play these lovers-turned-roommates, and things go from bad to worse.
Nicolas Cage has a prosthetic hand and Cher has great hair in this over-the-top but delicious film about an Italian-American woman falling for her fiancé's younger brother while the fiancé visits his dying mother in Sicily. The movie also popularized Dean Martin's version of "That's Amore," which will now be playing in your head for the rest of the week.
With Amy Schumer's writing and Judd Apatow's directing, this film perfectly captures the butterflies and dangers of taking things to the next level, ie. beyond the morning walk of shame. Bill Hader plays the guy Amy seriously falls for, even though her instincts tell her otherwise. LeBron James, Brie Larson, Vanessa Bayer, Tilda Swinton, Daniel Radcliffe, John Cena, and a slew of other famous people are in this.
28. Silver Linings Playbook
Pat and Tiffany's worlds collide all for the better after he's released from a mental institution and she deals with the fresh death of her husband. They become friends, rehearse for a dance competition, and for some reason, Bradley Cooper can't stop wearing a garbage bag.
29. The Wedding Planner
For a chunk of the 2000s, Matthew McConaughey couldn't stop making romantic comedies, and it was a blessing. In The Wedding Planner, Matthew plays an engaged man who falls for his…WEDDING PLANNER, played by J.Lo, who can’t seem to find "the one" despite her profession. Watch for brilliant performances from the always underrated Bridgette Wilson, Judy Greer, and a BB Justin Chambers, who would star on Grey's Anatomy four years later.
30. How To Lose A Guy In 10 Days
Would you ever buy a magazine called Composure? Doesn't matter. Kate Hudson's Andie Anderson writes for Composure and while she'd much rather tackle ~real topics like politics and poverty, her editor wants something juicy, giving birth to the movie's silly, silly title. The guy she tries to lose (for journalism) is rom-com king Matthew McConaughey, who also has a scheme of his own when he bets he can make any woman fall for him. Look, it's not hard IRL either, Matthew.
31. To All The Boys I've Loved Before
Lara Jean Covey (Lana Condor) has a habit of writing love letters to her crushes in order to get over them. When the letters get sent out by accident, all (good) hell breaks loose. Enter: Noah Centineo's Peter Kavinsky. Based on Jenny Han's YA novel of the same name, TATBILB has a movie sequel in the works, aptly titled P.S. I Still Love You.
32. Book Club
Four friends (played by Diane Keaton, Jane Fonda, Candice Bergen, and Mary Steenburgen) read Fifty Shades Of Grey for their long-running monthly book club. Need we say more?
33. Crazy Rich Asians
Girl meets guy. Guy turns out to be secretly rich. Like, crazy rich. Girl finds out while en route to meet guy's seriously loaded family in Singapore, complete with the gossipy relatives and one mother who thinks she knows best for her son. Henry Golding, Constance Wu, Michelle Yeoh, Awkwafina, and a cast of incredibly talented people star in this groundbreaking film based on Kevin Kwan's bestselling novel of the same name.
34. Set It Up
Lucy Liu plays a big-time editor who gets set up with a venture capitalist (Taye Diggs) who works in the same building. Such is the work of Harper and Charlie (Zoey Deutch and Glen Powell, respectively), two assistants who hatch a plan to make their bosses fall in love so they can have a social life that begins at a respectable time.
35. Friends With Benefits
Mila Kunis and Justin Timberlake are—you guessed it—friends with benefits, aka they hook up and vow to not fall in love while doing so. Which backfires, obviously, but that's where the romance comes in. Oh, and there are several flash mobs, which, let's be honest, make the movie.
36. The Proposal
Sandra Bullock plays a Canadian book editor facing deportation, that is until she devises the ultimate scam of claiming to be engaged to her hot AF assistant played by Ryan Reynolds. Which only leaves us wondering: Can I almost be deported if I get to end up with Ryan Reynolds? LMK.
37. Forgetting Sarah Marshall
Jason Segel gets dumped by his up-and-coming actress girlfriend (Kristen Bell) who also starts immediately dating Russell Brand. All three (+ Jason's love interest, played by Mila Kunis) end up in Hawaii together...at the same resort. Chaos ensues. New love follows. And there's a Paul Rudd cameo. Ahh, romance.
38. 50 First Dates
It doesn't get more rom-com than an Adam Sandler/Drew Barrymore combo. Henry (Adam) wants to win over Lucy (Drew), but he doesn't realize she has short-term memory loss, meaning he has to repeatedly win her over every single day. If the ending of this film doesn't make you cry, plz seek a professional.
This article originally appeared on Cosmopolitan.com. Minor edits have been made by the Cosmo.ph editors.