60 Best Romantic Comedies For Movie Night

60

Never Been Kissed (1999)

Josie Geller (Drew Barrymore) is a nerd-turned-reporter who goes undercover at her old high school—and ends up catching feelings for the dreamy English teacher (Michael Vartan). It’s peak late-‘90s cringe and charm, with awkward moments galore, a killer prom scene, and a romance that’ll leave you rooting for that final kiss on the baseball field.

59

She’s All That (1999)

A classic ‘makeover bet’ rom-com that practically defined the genre. Freddie Prinze Jr. plays a high school golden boy who bets he can turn artsy outsider Laney Boggs (Rachael Leigh Cook) into prom queen—and learns a thing or two about love along the way. Yes, it’s predictable, but that’s part of the fun. Think: paint-splattered dates, slow claps, and teen angst in all its late-’90s glory.

58

He’s Just Not That Into You (2009)

This ensemble rom-com tackles modern dating with a who’s-who of early 2000s stars—Jennifer Aniston, Ben Affleck, Scarlett Johansson, Bradley Cooper, Drew Barrymore, and more. It’s messy, relatable, and full of those “yep, been there” moments as it weaves together a bunch of interconnected love stories and heartbreaks. Some hit harder than others, but it’s still a comfort watch for fans of chaotic romance.

57

Sixteen Candles (1984)

John Hughes’ Sixteen Candles is an ’80s teen rom-com staple, following poor Samantha (Molly Ringwald), whose family forgets her birthday—and whose crush, Jake Ryan, might actually like her back. It’s got awkward siblings, weird grandparents, and big hair. While it delivers on nostalgia, it’s also worth noting some moments haven’t aged well.

56

She’s the Man (2006)

Amanda Bynes goes full Shakespeare in this gender-bending rom-com inspired by Twelfth Night. Viola disguises herself as her brother to join the boys’ soccer team, only to fall hard for her roommate (a baby-faced Channing Tatum). Between the slapstick chaos and the surprisingly sweet romance, it’s the kind of teen movie that still holds up for the sheer fun of it.

55

Enchanted (2007)

What happens when a fairytale princess lands in gritty NYC? Enchanted brings Disney magic into the real world with Amy Adams as the impossibly optimistic Giselle, who stumbles into the life of a cynical divorce lawyer (Patrick Dempsey). With musical numbers, an evil queen, and a dash of real-world romance, this one’s pure feel-good fantasy with a wink.

54

The Princess Diaries (2001)

Before Genovia was a TikTok meme, it was the fictional kingdom that made Mia Thermopolis (Anne Hathaway) a princess overnight. With Julie Andrews as her regal (and hilariously strict) grandmother, this coming-of-age rom-com is all about glow-ups, girl power, and learning to embrace who you are—even if that means ruling a country.

53

Legally Blonde (2001)

Elle Woods (Reese Witherspoon) follows her ex to Harvard Law in hopes of winning him back—but ends up proving she’s more than just a blonde with great fashion sense. Funny, empowering, and endlessly quotable, Legally Blonde is the kind of rom-com that doubles as a self-confidence booster.

52

Mamma Mia! (2008)

Set on a sun-drenched Greek island and soundtracked by ABBA bangers, this musical rom-com follows Sophie (Amanda Seyfried) as she tries to figure out who her dad is—by inviting three of her mom’s old flames to her wedding. It’s chaotic, silly, and irresistibly joyful. Meryl Streep dancing in overalls? Sold.

51

Beyond the Lights (2014)

This underrated gem follows Noni (Gugu Mbatha-Raw), a pop star on the edge, and Kaz (Nate Parker), the quiet cop who helps her find her voice again. With stunning visuals, raw emotion, and a deeply romantic core, this isn’t your typical rom-com—it’s moodier, sexier, and more soulful.

50

Someone Great (2019)

Freshly heartbroken and gearing up for a cross-country move, Jenny (Gina Rodriguez) rounds up her besties for one last wild night in NYC. More about friendship and healing than finding “the one,” Someone Great blends breakup blues with feel-good chaos and has one of the best female friendship dynamics out there.

49

Emma (2020)

If you love sharp wit, eye-popping fashion, and a touch of matchmaking chaos, this stylish Jane Austen adaptation is for you. Anya Taylor-Joy brings a delightfully snobby charm to Emma Woodhouse, a woman who just can’t stop meddling in other people’s love lives—until her own heart gets involved. It’s peak pastel aesthetic meets period comedy with real emotional depth.

48

Love, Simon (2018)

This heartfelt coming-of-age rom-com follows Simon, a closeted teen navigating his first love—through anonymous emails. As he tries to uncover the identity of his mystery crush, Simon’s world shifts in ways he never expected. Sweet, funny, and full of warmth, it’s a teen rom-com with heart and representation.

47

Say Anything (1989)

The boom box scene alone makes Say Anything iconic, but there’s more to it than that. John Cusack is endlessly lovable as the underdog Lloyd, who falls for brainy beauty Diane. It’s a gentle, soulful story about first love that feels honest, awkward, and genuinely touching.

46

About Time (2013)

This time-travel rom-com sneaks up on you emotionally. Tim (Domhnall Gleeson) discovers the men in his family can travel through time—and instead of saving the world, he uses it to find love with Mary (Rachel McAdams). Whimsical, heartfelt, and quietly profound, About Time is about so much more than just romance.

45

Always Be My Maybe (2019)

Childhood besties turned near-strangers, Sasha and Marcus reunite after years apart—and old sparks start to fly. Ali Wong and Randall Park have amazing chemistry, but let’s be real: Keanu Reeves playing a ridiculous version of himself steals the show. It’s charming, hilarious, and refreshingly modern.

44

Overboard (1987)

Goldie Hawn plays an amnesiac heiress, and Kurt Russell is the salty carpenter who tricks her into thinking she’s his wife. Is it ethically questionable? Absolutely. But it’s also a screwball comedy staple with laugh-out-loud moments and real chemistry between its leads.

43

Hitch (2005)

Will Smith is a smooth-talking “date doctor” helping hopeless romantics find love—until he meets Sara (Eva Mendes), a journalist who sees through his charm. Watching his tactics backfire is pure comedy gold, and the side romance with Kevin James is surprisingly adorable too.

42

Crazy, Stupid, Love (2011)

One divorce, one glow-up, and one surprise plot twist later, Crazy, Stupid, Love delivers a hilarious and heartfelt look at love in all its forms. Ryan Gosling teaching Steve Carell how to flirt? Iconic. Emma Stone and the Dirty Dancing lift? Even better. It’s clever, chaotic, and so much fun.

41

50 First Dates (2004)

Every day, Lucy wakes up with no memory of the day before—and Henry (Adam Sandler) is determined to win her heart again and again. Equal parts goofy and sweet, this Hawaii-set love story somehow makes amnesia romantic. It’s one of Sandler’s softest, most lovable roles.

40

Knocked Up (2007)

A one-night stand turns into a full-blown life shakeup when Alison (Katherine Heigl) finds out she’s pregnant—and the father is lovable man-child Ben (Seth Rogen). With awkward laughs and a surprising dose of heart, this raunchy rom-com dives into growing up when it matters most.

38

Love Jones (1997)

After a chance encounter at a Chicago club, budding writer Darius Lovehall (Larenz Tate) and aspiring photographer Nina Mosley (Nia Long) are thrust into a whirlwind romance that is soon tested when she moves to New York to rekindle her relationship with her ex-fiancé.

37

Moonstruck (1987)

Cher is at her absolute best in this offbeat rom-com about love, family, and fate. After getting engaged to one brother, Loretta unexpectedly falls for the other—the fiery, one-handed Ronny (Nicolas Cage). Equal parts absurd and romantic, it’s a weird little masterpiece.

36

The Holiday (2006)

Two women, two heartbreaks, and one spontaneous house swap later—romance blooms in all the right places. Cameron Diaz and Jude Law sizzle, while Kate Winslet and Jack Black give us something softer and sweeter. It’s cozy, emotional, and the ultimate winter watch.

35

Forgetting Sarah Marshall (2008)

When Peter gets dumped by his TV star girlfriend, he escapes to Hawaii—only to find she’s vacationing there too with her new rockstar boyfriend. Cringe comedy meets emotional healing in this hilarious heartbreak recovery movie that turns into something unexpectedly sweet.

34

The Princess Bride (1987)

This cult classic has it all: fencing, true love, Rodents of Unusual Size, and the endlessly quotable “As you wish.” Framed as a bedtime story, it follows Buttercup and Westley’s epic romance filled with swashbuckling adventure and fairytale absurdity. Equal parts parody and heart, it’s the ultimate comfort rom-com fantasy.

33

Definitely, Maybe (2008)

Ryan Reynolds is peak charming dad mode in this underrated gem. When his daughter asks how he met her mom, he turns it into a romantic mystery—telling her (and us) about the three major loves of his life. It’s sweet, reflective, and just the right amount of bittersweet.

32

Groundhog Day (1993)

Bill Murray plays a grumpy weatherman cursed to relive the same day over and over in small-town Pennsylvania. At first, it’s chaotic. Then it’s existential. Eventually… it’s romantic. Watching him fall for Andie MacDowell’s character while becoming a better human? Timeless.

31

Brown Sugar (2002)

Can you fall in love the same way you fell for music? Childhood friends Sidney (Sanaa Lathan) and Andre (Taye Diggs) built their lives around hip-hop—but never quite admitted their feelings. A soulful, grown-up rom-com with smooth vibes and an amazing soundtrack.

30

27 Dresses (2008)

Jane has been in more bridesmaid dresses than she can count—but when her sister gets engaged to the man Jane secretly loves, things get messy. Enter James Marsden’s snarky journalist. It’s the ultimate “always the bridesmaid” rom-com, and surprisingly emotional underneath all the tulle.

29

Serendipity (2001)

What if the universe had to bring you back to your soulmate? That’s the premise behind this snowy, fate-driven rom-com where two strangers have a magical night and leave their future up to chance. John Cusack and Kate Beckinsale bring the longing—perfect for hopeless romantics.

28

There’s Something About Mary (1998)

Cameron Diaz is the ultimate dream girl in this outrageous rom-com full of slapstick chaos, cringe humor, and a whole lot of guys trying (and failing) to win her heart. It’s raunchy, ridiculous, and somehow still kind of sweet underneath all the mayhem.

27

The Photograph (2020)

In the wake of her mother’s death, Mae Morton (Issa Rae) discovers a photograph that sends her on a journey into her estranged mother’s past. While investigating, an unexpected affair blossoms between her and Michael Block (Lakeith Stanfield), an up-and-coming journalist.

26

Breakfast at Tiffany’s (1961)

Audrey Hepburn is unforgettable as Holly Golightly—a free-spirited New Yorker chasing rich men while avoiding real connection. Enter Paul, her sweet writer neighbor. It’s stylish, iconic, and complicated (with some outdated elements), but the fashion and mood are forever.

25

Four Weddings and a Funeral (1994)

Weddings, heartbreak, and chance encounters—this British rom-com nails all of it. Hugh Grant stumbles through a series of romantic misfires and missed chances before realizing who he really wants. Charming, funny, and just a little bit weepy.

24

Something’s Gotta Give (2003)

When aging playboy Harry (Jack Nicholson) has a heart attack, he’s forced to recover under the care of his girlfriend’s mom—fierce and fabulous Erica (Diane Keaton). The slow-building spark between them is as funny as it is unexpectedly tender. A love story that proves you’re never too old to fall hard.

23

The Wedding Singer (1998)

Robbie (Adam Sandler) is a heartbroken wedding singer. Julia (Drew Barrymore) is engaged to the wrong guy. Together? Romantic gold. With a killer ‘80s soundtrack and just the right amount of awkward charm, this is one of the most endearing rom-coms of its era.

22

Clueless (1995)

As if we could leave this off the list! Alicia Silverstone’s Cher is a Beverly Hills queen bee with a heart of gold—and a thing for makeover projects. But in her quest to fix everyone else’s love life, she accidentally finds herself falling for the guy who knows her best. It’s iconic, endlessly quotable, and surprisingly wholesome.

21

The Big Sick (2017)

Based on Kumail Nanjiani’s real-life love story, this indie rom-com blends culture clash, medical crisis, and stand-up comedy into something totally unique. Kumail and Emily (Zoe Kazan) fall for each other—but their relationship is tested when she falls into a coma. Surprisingly funny, deeply moving, and so worth watching.

20

Sweet Home Alabama (2002)

Before Reese Witherspoon was making you cry on The Morning Show, she was choosing between her Southern roots and a Manhattan dream life in this charming rom-com. When Melanie returns home to finalize a divorce from her first love, sparks fly—and her small-town past starts pulling her back in.

19

Love & Basketball (2000)

A love story told in four quarters—Love & Basketball follows Monica and Quincy from childhood friends to teammates to something so much more. They grow up side by side, chasing their basketball dreams while falling in and out of each other’s lives. Passionate, grounded, and deeply romantic.

18

The Wedding Planner (2001)

J.Lo shines as Mary Fiore, a detail-obsessed wedding planner who breaks her own rule: never fall for the groom. Especially not the charming pediatrician who saves her from a runaway dumpster. It’s pure early 2000s rom-com magic—cheesy, sweet, and iconic.

17

The Proposal (2009)

Sandra Bullock plays a fierce, icy book editor who ropes her assistant (Ryan Reynolds) into a fake engagement to avoid deportation. What starts as blackmail turns into a hilariously awkward weekend with his family in Alaska—and maybe something real. Bonus: Betty White steals every scene.

16

(500) Days of Summer (2009)

This isn’t a love story—it’s a story about love. Tom falls head over heels for Summer. Summer… doesn’t believe in love. This indie rom-com explores infatuation, heartbreak, and how our memories don’t always match reality. Funny, honest, and quietly gutting.

15

Love Actually (2003)

Whether you love it or love to hate it, Love Actually is the holiday rom-com blueprint. Nine interconnected stories weave together tales of love lost, found, and everything in between—set against the twinkly backdrop of Christmas in London. It’s messy, emotional, and oddly comforting.

14

How To Lose a Guy in 10 Days (2003)

He thinks he can make any woman fall for him. She’s trying to make a guy run for the hills in ten days. Andie and Ben’s wild romantic experiment turns into something real in this battle of the sexes rom-com packed with iconic moments (hello, frost yourself ad and you’re so vain).

12

To All The Boys I’ve Loved Before (2018)

Lara Jean’s secret love letters accidentally get mailed out to her past crushes—and her life immediately spirals into adorable, chaotic drama. Enter Peter Kavinsky, the swoony jock who agrees to a fake relationship that feels way too real. Netflix’s teen rom-com era started here.

11

Bridget Jones’s Diary (2001)

Bridget Jones is chaotic, relatable, and 100% loveable. Between her career woes, cringey public moments, and romantic missteps (looking at you, Daniel Cleaver), she somehow stumbles her way into a proper love triangle with two very English men. Colin Firth in that reindeer jumper? Iconic.

10

Sleepless in Seattle (1993)

Tom Hanks and Meg Ryan don’t meet until the very end—and yet the chemistry is undeniable. After hearing widower Sam pour his heart out on a radio show, Annie becomes convinced he’s “the one.” Sweet, sentimental, and proof that sometimes love finds you in unexpected ways.

9

Think Like A Man (2012)

What happens when a group of girlfriends start taking love advice from Steve Harvey’s book? Their boyfriends decide to turn the tables. Think Like A Man is equal parts relationship comedy and dating game—with a great ensemble cast and tons of laugh-out-loud moments.

8

My Best Friend’s Wedding (1997)

Julia Roberts plays the ultimate chaotic heroine in this story of a woman who realizes she’s in love with her best friend… just days before his wedding. Instead of confessing her feelings, she plots to sabotage it. Messy? Yes. But oh so watchable.

7

Pretty Woman (1990)

Vivian never expected her week to include Rodeo Drive makeovers, polo matches, and falling in love with a client. Richard Gere’s suave businessman and Julia Roberts’ charming, street-smart sex worker make rom-com magic in this Cinderella story with major heart.

6

You’ve Got Mail (1998)

Before dating apps, there was anonymous AOL chat. Meg Ryan and Tom Hanks fall for each other online—without realizing they’re rivals in real life. It’s cozy, clever, and packed with bookstore charm. Proof that email love letters can still make your heart flutter.

5

4

13 Going on 30 (2004)

13 Going on 30 had us all wishing to be “Thirty, Flirty and Thriving.” From the killer 80s soundtrack to the bitchin wardrobe to the unforgettable scene where Jenna (Jennifer Garner) livens up the launch party by performing the iconic zombie dance, you can’t go wrong with this feel-good flick. Plus, the razzles. 

Rachel thinks she’s just tagging along to a friend’s wedding. Turns out, her boyfriend is heir to one of Asia’s wealthiest families—and the wedding is a full-blown royal-level spectacle. With stunning visuals, heartfelt moments, and a dreamy romance, this one’s a modern rom-com must.

2

When Harry Met Sally (1989)

Can men and women ever just be friends? This iconic rom-com explores that very question over a decade of missed connections, banter, and that deli scene. Witty, sharp, and timeless, it’s the rom-com blueprint for a reason.

1

10 Things I Hate About You (1999)

Kat Stratford has no interest in dating—but when her younger sister isn’t allowed to date until she does, a scheme unfolds involving the mysterious bad boy, Patrick Verona (played by Heath Ledger at his most swoon-worthy). Add in the iconic poem scene and the stadium serenade? Instant classic.