Ranking the 75 best romantic comedies of all time

Molly Ringwald and Michael Schoeffling in“Sixteen Candles.”
Molly Ringwald and Michael Schoeffling in“Sixteen Candles.” | Universal City
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A rom-com, or romantic comedy, is not simply a “chick flick.”

Not every film with humor and romance constitutes as a romantic comedy. To be a good rom-com, the humor stems from a romantic relationship.

“Romantic comedy films create a comic climate through a series of cues to the audience: subject matter is treated as trivial, jokes and physical humor make fun of events, and characters are protected from harm,” Leger Grindon, a professor of film and media culture, writes in “The Hollywood Romantic Comedy.”

He continues, “Even though the story poses serious problems, such as finding a life partner, the process appears lighthearted.”

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There are dozens of elements that make a rom-com worthwhile: a charming lead, relatable romance woes, a sappy declaration of love, a clever departure from the formula and a happily-ever-after ending. When the elements successfully come together, you end up with a perfect rom-com.

Here are the 75 best rom-coms of all time — ranked.

75. ‘500 Days of Summer’ (2009)

Joseph Gordon-Levitt and Zooey Deschanel in “500 Days of Summer.”
Joseph Gordon-Levitt and Zooey Deschanel in “500 Days of Summer.” | Twentieth Century Fox

When hopeless romantic Tom (Joseph Gordon-Levitt) is suddenly dumped by the girl he believed to be his soulmate (Zooey Deschanel), he reflects on their 500 days together — hoping to uncover what went wrong, only to rediscover what he enjoys most about life.

Why No. 75? Though technically a rom-com, “500 Days of Summer” is mostly a depressing story about a man who depends on a manic pixie dream girl to fill his lack of identity. A handful of moments warrant laughter and there is romance — but this is a movie about a man learning to fall in love with himself.

Rating: PG-13, for sexual material and language.

Where to watch: Max.

74. ‘The Notebook’ (2004)

Rachel McAdams and Ryan Gosling in “The Notebook.”
Rachel McAdams and Ryan Gosling in “The Notebook.” | Melissa Moseley, Melissa Moseley/newline.wireimag

Mill worker Noah Calhoun (Ryan Gosling) and wealthy girl Allie (Rachel McAdams) fall madly in love in 1940s South Carolina. When Noah goes to war, Allie begins dating Lon (James Marsden). But when Noah returns on the brink of Allie’s wedding day, it is clear the spark between them has not gone out.

Why No. 74? Noah is creepily obsessed with Allie and manipulates her into going out with him. The pair have a toxic relationship. Allie would have been treated better by Lon.

Also, “The Notebook” is barely funny.

Rating: PG-13, for some sexuality.

Where to watch: Hulu, Max.

73. ‘This Means War’ (2012)

CIA operatives FDR Foster (Chris Pine) and Tuck (Tom Hardy) are best friends and colleagues. They thought nothing could come between them. But their longstanding professional relationship and friendship is put on the line when they discover they are interested in the same woman, Lauren (Reese Witherspoon). The pair agrees to let Lauren decide which man is a better fit for her. Using their deadly skills, high-tech gadgets and world-class spying abilities, they begin an intense battle for romance.

Why No. 73? Hilarious, but the romance takes a back seat in this movie.

Rating: PG-13, for sexual content, some violence and action, and language.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

72. ‘Austenland’ (2013)

“Austenland.”
“Austenland.” | Giles Keyte

Jane Hayes (Keri Russell) is obsessed with the Jane Austen novels and fantasizes about Mr. Darcy on the regular. She uses her savings to go to Austenland, a British resort that immerses its guests in an Austen-worthy romance, and she might finally meet her own Mr. Darcy.

Why No. 72? Mostly because Jennifer Coolidge’s character is so funny.

Rating: PG-13 for some suggestive content and innuendo.

Where to watch: Starz.

71. ‘Say Anything’ (1989)

Charming underachiever Lloyd (John Cusack) and unattainable overachiever Diane (Ione Skye) fall in love over the summer before she leaves home for college. But Diane’s overly-protective divorced father (John Mahoney) does not approve of their relationship, and it will take a lot more than their feelings for each other to earn his approval.

Why No. 71? The iconic boombox blasting “In Your Eyes” scene is the only thing keeping this movie on the map. The rest of movie goes by at a snail’s pace and doesn’t hold up with a modern audience.

Rating: PG-13, for mild profanity and sexual content.

Where to watch: Rent from Amazon Prime, YouTube TV, Apple TV.

70. ‘One Fine Day’ (1996)

Single parents Melanie Parker (Michelle Pfeiffer) and Jack Taylor (George Clooney) are both buried in work and desperate for babysitters when both their children miss the bus for the school field trip. The pair strike a deal to juggle babysitting duties, but their plan doesn’t run as smoothly as they hoped.

Why No. 70? A fun one-time watch, but not very memorable.

Rating: PG, for language and mild sensuality.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

69. ‘Maid in Manhattan’ (2002)

Jennifer Lopez in “Maid in Manhattan.”
Jennifer Lopez in “Maid in Manhattan.”

Marisa Ventura (Jennifer Lopez) is a single mother and first-class hotel maid in New York City. By accident, Marisa meets Christopher Marshall (Ralph Fiennes), the heir to a political dynasty. He mistakes her as a guest at the hotel and the pair share a magical evening together, but when her true identity is revealed, they realize how different they truly are.

Why No. 69? There are dozens of “Cinderella” adaptations, but this one still somehow feels more cookie-cutter than most. Chris’s bland personality is a drag, and there is a shortage of chemistry between Fiennes and Lopez that make the romance dry.

Rating: PG-13, for some language and sexual references.

Where to watch: Max.

68. ‘Sweet Home Alabama’ (2002)

Reese Witherspoon, Patrick Dempsey and Candice Bergen in “Sweet Home Alabama.”
Reese Witherspoon, Patrick Dempsey and Candice Bergen in “Sweet Home Alabama.” | Peter Iovino, Buena Vista Pictures

From the outside, Melanie’s (Reese Witherspoon) life looks perfect. She is an up-and-coming fashion designer engaged to one of New York’s most eligible bachelors. But Melanie has skeletons in her closet — the young designer must return to her home state of Alabama to cover up her past. Melanie finds herself in trouble when she discovers she’s still married to her high school sweetheart.

Why No. 68? A love triangle is always entertaining, but she picks the wrong guy.

Rating: PG-13, for language and sexual references.

Where to watch: Disney+.

67. ‘The Princess Diaries 2: Royal Engagement’ (2004)

Callum Blue, Anne Hathaway and Chris Pine in “Princess Diaries 2: Royal Engagement.”
Callum Blue, Anne Hathaway and Chris Pine in “Princess Diaries 2: Royal Engagement.”

As she continues to come to grips with her newfound royal title, Mia (Anne Hathaway) discovers she must get married in the next 30 days or she cannot become queen. The charming Nicholas Devereaux (Chris Pine) is one of Mia’s favorite suitors, but he has more on his mind than Mia — he wants the crown.

But once Nicholas realizes he has developed true feelings for Mia, he decides to back off.

Why No. 67? We are eternally indebted to Disney for casting Chris Pine in a “Princess Diaries” sequel.

Rating: G.

Where to watch: Hulu, Disney+.

66. ‘Annie Hall’ (1977)

Comedian Alvy Singer (Woody Allen) reflects on his relationship with nightclub singer Annie Hall (Diane Keaton) — how they met, when it fell apart and humorous insights on the difficulty of romance.

Why No. 66? Through humor, “Annie Hall” captures the nerves of a burgeoning romance. But the best part of this movie is the wardrobe.

Rating: PG, for mild profanity.

Where to watch: Amazon Prime.

65. ‘Runaway Bride’ (1999)

Maggie Carpenter (Julia Roberts) has a reputation for ditching men at the altar — earning her the nickname “runaway bride.” When a big-city newspaper journalist (Richard Gere) gets wind of Maggie’s wedding-day habit, he wants to write a story on it.

While investigating Maggie’s three runaway moments, he cannot help but catch feelings for her.

Why No. 65? It’s a good family-friendly rom-com, but the story isn’t remarkable. One of the highlights is seeing “Pretty Women” co-stars Julia Roberts and Richard Gere prove they are still a rom-com match made in heaven.

Rating: PG, for some language.

Where to watch: Paramount+.

64. ‘50 First Dates’ (2004)

Drew Barrymore and Adam Sandler in “First 50 Dates.”
Drew Barrymore and Adam Sandler in “First 50 Dates.” | Sony

The Adam Sandler and Drew Barrymore duo never disappoints. Sandler plays Henry, a playboy who is used to getting his way. Lucy (Barrymore) is an unusual challenge for Henry to woo because she suffers from short-term memory loss. Every day, Henry must woo Lucy all over again, and prove to Lucy’s protective family he truly cares for her.

Why No. 64? The Sandler and Barrymore duo is the saving grace of this movie. As far as rom-coms go, it’s not very romantic (since Lucy cannot remember who Henry is) and, if you think about it, is kind of depressing.

Rating: PG-13, for crude humor.

Where to watch: Netflix.

63. ‘Moonstruck’ (1987)

Nicolas Cage and Cher in “Moonstruck.”
Nicolas Cage and Cher in “Moonstruck.” | Moonstruck MGM

Loretta Castorini (Cher), a Brooklyn bookkeeper, agrees to marry a man she does not love. Her life get complicated when she falls for her fiancé’s younger brother, Ronny (Nicolas Cage). Loretta tries to resist her growing feelings for Ronny, but his passionate temperament gives way to a romance she cannot pass up.

Why No. 63? “Moonstruck” strays from the beaten path and deploys original humor to remind viewers what it looks like to settle in romance — juxtaposed with a passionate relationship, urging audiences to rediscover what love should look like.

Rating: PG, for some language.

Where to watch: Hulu.

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62. ‘Roxanne’ (1987)

In this modern take on the classic play “Cyrano de Bergerac,” by Edmond Rostand, C.D. Bales (Steve Martin) is the witty, brave fire chief of a small Pacific Northwest town. But he struggles to pursue the girl of his dreams due to insecurities about his enormous nose. But when his shy underling, Chris McConnell (Rick Rossovich), also falls for Roxanne (Daryl Hannah), he feeds the good-looking young man the right words to win her heart.

Why #62? Through a blend of delicate and slapstick humor, “Roxanne” brings modern life to one of the original rom-coms, “Cyrano de Bergerac.”

Rating: PG, for mild language.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

61. ‘Kate and Leopold’ (2001)

Meg Ryan and Hugh Jackman in “Kate & Leopold.”
Meg Ryan and Hugh Jackman in “Kate & Leopold.”

Kate McKay (Meg Ryan) is a driven businesswoman who doesn’t make time for romance. Leopold, the third Duke of Albany (Hugh Jackman), is a charming bachelor from the late 1800s. When a tear in the space-time continuum lands Leopold in modern New York City, they cannot help but fall for one another — despite their obvious differences.

Why No. 61? “Kate and Leopold” is nothing to write home about. It is a fun watch, but Ryan’s performance feels half-hearted and the story gets a little too sappy at times.

Rating: PG-13, for brief strong language.

Where to watch: Max, Hulu, Amazon Prime.

60. ‘Serendipity’ (2001)

“Serendipity” attempts to answer the questions we have all asked ourselves — is fate in control of our love lives? Jonathan (John Cusack) and Sara (Kate Beckinsale) meet in their 20s and instantly hit it off. For Jonathan, it is love at first sight. Sara wants destiny to decide if they should be together. Ten years later, they must decide if they are fated to be together.

Why No. 60? “Serendipity” is the cinematic manifestation of our romantic delusions — the belief that fate, rather than choice, rules our love lives. It is an interesting concept, but 90 minutes of near-misses gets annoying to watch.

Rating: PG-13, for brief language and sexuality.

Where to watch: Amazon Prime, Paramount+, Netflix.

59. ‘The Holiday’ (2006)

Kate Winslet and Jack Black in “The Holiday.”
Kate Winslet and Jack Black in “The Holiday.” | Zade Rosenthal, Zade Rosenthal

Two women fed up with their dating lives decide to switch houses for the holidays and take a break from men. Amanda (Cameron Diaz) finds herself in a charming English town, while Iris (Kate Winslet) takes over Amanda’s Beverly Hills mansion. But both ladies soon find themselves drawn to local men, providing a much-needed romantic pick-me-up.

Why No. 59? Loses points for being too seasonal. It would be inappropriate to watch this movie outside of Christmastime — though it’s still one of the best Christmas rom-coms. The only thing that would make it better is if the entire movie followed Jack Black and Kate Winslet’s story line.

Rating: PG-13, for sexual content and some strong language.

Where to watch: Starz.

58. ‘Sleepless in Seattle’ (1993)

Meg Ryan, Ross Malinger, and Tom Hanks in “Sleepless in Seattle.”
Meg Ryan, Ross Malinger, and Tom Hanks in “Sleepless in Seattle.” | AP, TriStar Pictures Inc

Sam Baldwin (Tom Hanks) moves to Seattle after the death of his wife. Sam’s son, Jonah (Ross Malinger), calls a talk-radio program to find his father a new wife. Annie Reed (Meg Ryan) hears Jonah’s message and immediately falls in love with Sam, even though she is engaged. Annie, a journalist, uses her skills to learn more about him — and wrestles with her inexplicable attraction to Sam and her love for her fiancé.

Why No. 58? “Sleepless in Seattle” is sleepy. The entire movie drags on to an ending that is wholly unsatisfying. The two best parts are Meg Ryan and Tom Hanks — which count for a lot.

Rating: PG, for some language.

Where to watch: Showtime, Amazon Prime, Hulu.

57. ‘Bridget Jones’s Diary’ (2001)

Colin Firth and Renée Zellweger in “Bridget Jone’s Diary.”
Colin Firth and Renée Zellweger in “Bridget Jone’s Diary.” | ©2004 Universal Studios and Studio Canal and Miramax Film Corp

At the start of the new year, Bridget Jones (Renée Zellweger) vows to improve herself as she searches for love. When her boss, Daniel Cleaver (Hugh Grant), begins openly flirting with her, she dives right in.

Meanwhile, she keeps running into the stiff lawyer, Mark Darcy (Colin Firth), who confesses his feelings in spite of her imperfections.

Why No. 57? It’s the modern take on “Pride and Prejudice” we didn’t know we needed.

Rating: R, for language and sexuality.

Where to watch: Paramount+.

56. ‘Bridesmaids’ (2011)

Annie (Kristen Wiig) feels betrayed when her lifelong best friend, Lillian (Maya Rudolph), lets her newfound friend take the lead on wedding planning.

Desperate for attention, Annie’s juvenile behavior threatens to ruin her friendship with Lillian as well as a shot at love with a charming police officer (Chris O’Dowd).

Why No. 56? The film is hilarious. But the romance feels like a secondary plot and Annie becomes so unhinged it gets hard to watch.

Rating: R, for language and sexuality.

Where to watch: Amazon Prime.

55. ‘Love & Basketball’ (2000)

Monica (Sanaa Lathan) and Quincy (Omar Epps) are aspiring pro-basketball players and childhood best friends. Through a shared love of basketball and several ups and downs, the pair of best friends begin to fall for each other but their evolving life paths threaten to tear them apart.

Why No. 55? “Love & Basketball” walked so “High School Musical” could run.

Rating: PG-13, for sexuality and language.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

54. ‘Reality Bites’ (1994)

After college graduation, Lelaina (Winona Ryder) films a documentary highlighting the difficulties of beginning a career and maintaining meaningful relationships.

Nerdy career-man Michael (Ben Stiller) romances Lelaina and offers to help her get the documentary on TV. In spite of her growing feelings for Micheal, Lelaina struggles to ignore the romantic tensions she shares with Troy (Ethan Hawke) — her moody best friend suffering from an existential crisis.

Why No. 54? The final scene where Troy and Lelaina finally express how they feel never fails to make me tear up. Sometimes I watch “Reality Bites” when I feel like crying.

Rating: PG-13, for language and sensuality.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

53. ‘The Prince and Me’ (2004)

Julia Stiles as Paige and Luke Mably as Eddie in “The Prince & Me.”
Julia Stiles as Paige and Luke Mably as Eddie in “The Prince & Me.” Paramount Pictures.

Studious college student Paige (Julia Stiles) is prepared to let nothing get in the way of her and medical school. She’s thrown for a loop when Eddie (Luke Mably), a handsome Danish student, is assigned as her lab partner. Despite her initial disdain for Eddie, Paige begins to fall for him. Little does she know, Eddie is the heir to Denmark’s throne.

Why No. 53? The movie is so shamelessly cheesy it actually works.

Rating: PG-13 for sexual content and language.

Where to watch: Paramount+.

52. ‘The Wedding Singer’ (1998)

Robbie (Adam Sandler) is a brokenhearted softie trying to recover from the pains of being left at the altar by his fiancée. Robbie is haunted by his past almost every day at work — he is a wedding singer. The hopeless romantic begins to see a second chance at love when he meets Julia (Drew Barrymore), a young woman who asks Robbie to help plan her wedding.

Why No. 52? The airplane scene when Billy Idol gives Robbie dating advice and assistance.

Rating: PG-13, for sex-related material and language.

Where to watch: HBO Max, Peacock.

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51. ‘Crazy, Stupid, Love’ (2011)

Ryan Gosling and Emma Stone in “Crazy, Stupid, Love.”
Ryan Gosling and Emma Stone in “Crazy, Stupid, Love.” | BEN GLASS, BEN GLASS

When Cal Weaver’s (Steve Carell) beautiful wife (Julianne Moore) asks for a separation, his seemingly perfect life unravels and he finds himself desperately unfit to reenter the dating world. With help from charming bachelor Jacob Palmer (Ryan Gosling), Cal begins to learn what it takes to be a hit with the ladies.

Why No. 51? It’s loaded with dramatic irony that keeps you laughing the whole way through. There’s also a healthy dose of romance.

Rating: PG-13, for coarse humor, sexual content and language.

Where to watch: Hulu.

50. ‘The Duff’ (2015)

Mae Whitman in “The Duff.”
Mae Whitman in “The Duff.” | Guy D Alema, CBS Films

When high school senior Bianca (Mae Whitman) learns her classmates secretly consider her a DUFF — designated ugly fat friend — to her beautiful, popular friends, she decides to reinvent herself. She enlists the help of her longtime friend and neighbor, football star Wesley (Robbie Amell), to help her overcome the cruel label.

Bianca needs to muster enough confidence to stand up to a snobby classmate (Bella Thorne) and undermine the high school social pyramid.

Why No. 50? “The Duff” is basically a romantic version of “Mean Girls” — and I say that as a compliment.

Rating: PG-13, for crude and sexual material and some language.

Where to watch: Roku, Showtime.

49. ‘She’s All That’ (1999)

Big man on campus Zach Siler (Freddie Prinze Jr.) seems to have everything — the looks, the girlfriend, the car, the friends — but his popularity takes a sudden nosedive when his cheerleader girlfriend, Taylor (Jodi Lyn O’Keefe), dumps him for a tacky reality TV star.

To save his fragile reputation, Zach agrees to gain the trust of a nerdy classmate, Laney Boggs (Rachael Leigh Cook), and make her the next prom queen.

Why No. 49? OK, so makeover scenes aren’t really cool anymore, but “She’s All That” is loaded with other clichés, too: A popular guy falls for an uncool girl, a “fake dating” bet, a third-act declaration of love and a dead mom. Put these all together, add in Freddy Prinze Jr. and Paul Walker, and you get a classic ‘90s rom-com.

Rating: PG-13 for sexual content and language.

Where to watch: Rent from Amazon Prime, YouTube TV, Apple TV.

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48. ‘27 Dresses’ (2008)

Katherine Heigl in “27 Dresses. She plays a woman who’s never a bride, always a bridesmaid.”
Katherine Heigl in “27 Dresses.” | Barry Wetcher, Associated Press

Jane (Katherine Heigl) is always a bridesmaid and never the bride. The perpetual bridesmaid is obsessed with weddings but far from having one of her own. When Jane’s little sister Tess (Malin Ackerman) snags the man Jane has been hopelessly in love with for years, Jane decides it might be time to give up her role as the perfect bridesmaid.

Kevin, a handsome reporter (James Marsden), thinks Jane’s story provides him with the perfect article to get off the wedding beat.

Why No. 48? Marsden and Heigl have great chemistry. Also, the scene when Jane crashes a wedding and declares her feelings for Kevin is simultaneously the funniest and most romantic part of the movie.

Rating: PG-13, for language and sexuality.

Where to watch: Disney+.

47. ‘Housesitter’ (1992)

Architect Newton Davis (Steve Martin) is devastated when his girlfriend turns down a proposal and the home he designed for them to live in. He cannot imagine living in the home without her and shares his story with a waitress (Goldie Hawn), who decides to move into the empty home and pose as Newton’s girlfriend.

Why No. 47? Goldie Hawn.

Rating: PG, for mild sensuality and language.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

46. ‘French Kiss’

When Kate (Meg Ryan) learns that her fiancé has fallen in love with another woman, she boards a plane to France to win him back. On the plane, she is seated next to Luc (Kevin Kline), a French thief.

Why No. 46? Meg Ryan’s outfits.

Rating: PG-13 for some sexuality, language and drug references.

Where to watch: Rent on Amazon Prime.

45. ‘My Best Friend’s Wedding’ (1997)

Childhood friends Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) vowed to marry each other if they were both single at 28.

Just days before Julianne’s 28th birthday, Michael announces his plans to marry a beautiful 20-year-old named Kimberly (Cameron Diaz). In this moment, Julianne realizes she is in love with Michael and decides to break up the upcoming wedding.

Why No. 45? The act of breaking up a wedding makes for the right amount of drama and humor you expect from any good rom-com.

Rating: PG-13, for language.

Where to watch: Netflix.

44. ‘Some Kind of Wonderful’ (1987)

Eric Stoltz and Mary Stuart Masterson in “Some Kind of Wonderful.
Eric Stoltz and Mary Stuart Masterson in “Some Kind of Wonderful. Paramount Home Entertainment

Artsy, ostracized high school student Keith Nelson (Eric Stoltz), seeks help from his tomboy best friend Watts (Mary Stuart Masterson) to land a date with a pretty popular girl, Amanda Jones (Lea Thompson). But his attempts draw attention from Amanda’s  snobby ex-boyfriend, Hardy Jenns (Craig Sheffer), who plans to seek vengeance. Things get even more complicated when Watts realizes she has feelings for Keith.

Why No. 44? Everyone has fallen for a best friend. In those moments, this movie gets you.

Rating: PG-13, for some language.

Where to watch: HBO Max.

43. ‘Dan in Real Life’ (2007)

Steve Carrell and Juliette Binoche in “Dan in Real Life.”
Steve Carrell and Juliette Binoche in “Dan in Real Life.” | Merie W. Wallace / SMPSP, Merie W. Wallace / SMPSP

Overworked widower Dan Burns (Steve Carrell) offers excellent advice in his column, but struggles to raise his three daughters on his own. During a trip to the bookstore, Dan falls hard for a mysterious woman, Marie (Juliette Binoche), only to discover she is his younger brother’s (Dane Cook) new girlfriend.

While all stuck under the same roof for a family reunion, Dan suffers at the sight of his brother with Marie. Relationships get tense as Dan fails to hide how he feels.

Why No. 43? It’s tender watching a widowed single father get a second chance at love. It’s funny watching his thick-headed brother date the same woman.

“Dan in Real Life” also has something most rom-coms don’t — a balance of romantic and familial love that warms the heart in a unique way.

Rating: PG-13, for some innuendo.

Where to watch: Amazon Prime, Disney+.

42. ‘Overboard’ (1987)

Joanna (Goldie Hawn) is a beautiful but snobby heiress living a leisurely life with her husband. When Joanna falls overboard her yacht and suffers from amnesia, her husband takes it as an opportunity to get away from his difficult wife.

Joanna is taken in by Dean (Kurt Russell), a widowed father of four who once worked for Joanna. With no memory of her past, Joanna struggles to accept her new life as a mother.

Why No. 42? “Overboard” is guaranteed to make you laugh, but the romance part is a little dry considering Joanna is tricked into believing she loves Dean.

Rating: PG, for language.

Where to watch: HBO Max, Hulu.

41. ‘Silver Linings Playbook’ (2012)

Jennifer Lawrence and Bradley Cooper play a pair of mentally unstable singles in “Silver Linings Playbook.”
Jennifer Lawrence and Bradley Copper in “Silver Linings Playbook.” | Jojo Whilden

Pat Solatano (Bradley Cooper) moves back in with his parents (Robert De Niro, Jacki Weaver) in the wake of losing his wife and job. He is desperate to repair things with his wife and get his career back on track, but his parents have different expectations.

When Pat meets Tiffany (Jennifer Lawerence), she prove to be more troubled than he is. Tiffany promises to help Pat get back together with his wife if he does something for her in exchange.

Why No. 41? As far as movies go, “Silver Linings Playbook” is stellar. But it has heavy themes that take away from the lighthearted spirit expected from rom-coms.

Rating: R, for language and some sexual content.

Where to watch: Netflix.

40. ‘Shakespeare in Love’ (1998)

“Shakespeare in Love” (1998)
Gwyneth Paltrow and Joseph Fiennes in “Shakespeare in Love.”

A young William Shakespeare (Joseph Fiennes) is suffering from writer’s block and desperate for a new muse. He is inspired by a young, beautiful aristocrat (Gwyneth Paltrow), who provides the inspiration he needs to write one of his most famous plays.

Why No. 40? Witty, playful, romantic and satisfying, “Shakespeare in Love” breaks from the typical rom-com mold while staying true to the genre in spirit.

Rated: R, for sexuality.

Where to watch: Max.

39. ‘Return to Me’ (2000)

Bob Rueland (David Duchovny) is heartbroken after his wife’s sudden death in a car accident. His friend Charlie (David Alan Grier) encourages Bob to start dating again and sets him up on a blind date. Although the date is a bust, Bob is captivated by the waitress, Grace (Minnie Driver), a recovering heart transplant patient. When Bob discovers Grace’s new heart came from his organ donor wife, a romance begins to bloom.

Why No. 39? “Return to Me” wins as a mushy tear-jerker about second chances at love — but it’s not very funny.

Rating: PG for some language and thematic elements.

Where to watch: Hulu.

38. ‘Ever After: A Cinderella Story’ (1998)

In this “Cinderella” adaptation, Danielle (Drew Barrymore) is a lively young woman forced into servitude after the death of her father. Danielle’s cruel stepmother (Anjelica Huston) makes her carry out all the housework while she desperately tries to marry off her two bratty daughters. Things for Danielle improve when she meets the handsome Prince Henry (Dougray Scott).

Why No. 38? “Ever After” is a strong “Cinderella” adaptation that speaks to your inner little girl with whimsy, charm, adolescent romance and beautiful dresses.

Rating: PG for mild language.

Where to watch: Disney+.

37. ‘Something’s Gotta Give’ (2003)

Jack Nicholson and Diane Keaton in “Something’s Gotta Give.”
Jack Nicholson and Diane Keaton in “Something’s Gotta Give.”

Harry Sandborn (Jack Nicholson) is pushing mid-60s and still wants to date women far younger than him. When Harry and his young girlfriend, Marin (Amanda Peet), arrive at Marin’s family beach house, they discover her mother, Erica Barry (Diane Keaton) also had plans to stay.

Harry suffers from a heart attack and his doctor (Keanu Reeves) puts him on bed rest. During his stay, Harry realizes he may be falling for a woman his own age.

Why No. 37? “Something’s Gotta Give” is a successful reminder that you are never too old to fall in love again — and romance is even sweeter when the leads aren’t young 20-somethings.

Rating: PG-13, for brief partial nudity, language and sexual content.

Where to watch: Paramount+, Amazon Prime.

36. ‘Pretty in Pink’ (1986)

Molly Ringwald, Andrew McCarthy, Jon Cryer in “Pretty in Pink.”
Molly Ringwald, Andrew McCarthy, Jon Cryer in “Pretty in Pink.”

Andie (Molly Ringwald) is a high school outcast who either hangs out with her older work colleague (Annie Potts) or her quirky classmate Duckie (Jon Cryer), who has feelings for her. But when one of the popular boys at school, Blane (Andrew McCarthy), asks her out, it seems too good to be true. She quickly learns that dating someone from the popular group might be more trouble than its worth.

Why No. 36? It gets points for being a classic and featuring the Psychedelic Furs’ song “Pretty in Pink.” But Duckie is actually really irritating and Blane is a coward for 95% of the movie.

Rated: PG-13, for language, underage alcohol use and some suggestive material.

Where to watch: Max.

35. ‘Singin’ in the Rain’ (1952)

Don (Gene Kelly) and Lina (Jean Hagen) are repeatedly cast as a romantic couple, but when their most famous film is adapted into a musical, only Don can pull off the singing part. Even with loads of practice, Lina sounds terrible, so a young, aspiring actress, Kathy (Debbie Reynolds) is brought on to record her singing parts.

Why No. 35? Gene Kelly tapping about whilst belting “Singing in the Rain” sums up what it feels like to fall in love.

Rated: G.

Where to watch: Max.

34. ‘An Affair to Remember’ (1957)

Cary Grant and Deborah Kerr in “An Affair to Remember.”
Cary Grant and Deborah Kerr in “An Affair to Remember.” | Fox Home Entertainment

Nickie (Cary Grant) and Terry (Deborah Kerr) have a short-lived romance while taking a cruise ship from Europe to New York. They are both engaged to other people, but agree to meet at the top of the Empire State Building in six months. When a tragic accident keeps Terry from keeping their rendezvous, Nickie fears she married another man.

Why No. 34? The dramatic irony makes this movie a bit of a nail-biter (in the best way possible) and the meet-me-on-the-Empire-State-building scene has been reused dozens of times (like in “Sleepless in Seattle”). But while it is wildly romantic, it’s lacking in the humor department.

Rating: G.

Where to watch: Rent on Apple TV, YouTube TV.

33. ‘Jerry Maguire’ (1996)

When savvy sports agent Jerry Maguire (Tom Cruise) has a moral epiphany, he writes a heartfelt company-wide memo that gets him fired. Hoping to hold onto the athletes he represents, Jerry launches his own management firm, with only single mother Dorothy Boyd (Renee Zellweger) to join him. The pair begin to fall for each other as they struggle to get the business off the ground.

Why No. 33? “You had me at hello.”

Rating: R, for language and sexuality.

Where to watch: Peacock.

32. ‘Set it Up’ (2018)

Zoey Deutch and Glen Powell in “Set It Up.”
Zoey Deutch and Glen Powell in “Set It Up.” | Netflix

A pair of overworked and underpaid assistants hatch a plan to set up their workaholic bosses. As Charlie (Glen Powell) and Harper (Zoey Deutch) play matchmaker, they realize the right set-up might be themselves.

Why No. 32? Glen Powell and Zoey Duetch have the onscreen chemistry that takes a rom-com from mediocre to great. With a different cast, this movie wouldn’t be what it is.

Rating: TV-14, for some sexual references and some language.

Where to watch: Netflix.

31. ‘Sabrina’ (1995)

Sabrina (Julia Ormond) has long harbored feelings for David (Greg Kinnear), the playboy son of a wealthy family, for whom Sabrina’s father works as a chauffeur. When she returns from Paris, Sabrina has blossomed into a beautiful and glamorous woman that can get David’s attention.

Linus (Harrison Ford), David’s older brother, disapproves of the relationship. In his efforts to split them up, Linus falls for Sabrina.

Why No. 31? Romantic, but also empowering because Sabrina fulfills her dream of moving abroad and finds security in who she is before falling in love.

Rating: PG, for mild language.

Where to watch: Amazon Prime, Paramount+.

30. ‘Two Weeks Notice’ (2002)

Hugh Grant and Sandra Bullock in “Two Weeks Notice.”
Hugh Grant and Sandra Bullock in “Two Weeks Notice.” | PHOTO: ELI REED

Passionate environmental lawyer Lucy Kelson (Sandra Bullock) goes to work for billionaire George Wade (Hugh Grant) as part of a deal to preserve an environmental center. George becomes dependent on Lucy’s assistance on everything from legal advice to what tie to wear.

Frustrated, Lucy puts in her two weeks notice and hires a replacement (Alicia Witt) but as her time with George comes to an end, she begins having regrets.

Why No. 30? Through witty banter, “Two Weeks Notice” sets itself up early on as a will-they-won’t-they storyline. In a deeply relatable turn of events, Lucy and George must both humble themselves and admit they have feelings for each other.

Rated: PG-13, for some sex-related humor.

Where to watch: Hulu.

29. ‘Breakfast at Tiffany’s’ (1961)

Young New York socialite Holly (Audrey Hepburn) is looking to marry a wealthy, older man. Her plans get complicated when a young, aspiring writer (George Peppard) moves into Holly’s building and catches her eye.

Why No. 29? Through offbeat humor and tender romance, “Breakfast at Tiffany’s” sets a high bar for rom-coms to come — hundreds have failed to live up to the expectations “Tiffany’s” set.

Rating: G.

Where to watch: Paramount+.

28. ‘Pretty Woman’ (1990)

“Pretty Woman” (1990)
“Pretty Woman” (1990)

Edward (Richard Gere), a wealthy business man, hires Hollywood Boulevard call girl Vivian (Julia Roberts) to escort him to social events while he is in town. Spending the week with Edward changes Vivian’s world, and the pair begin to truly fall for each other.

Why No. 28? OK, so the premise is a little outrageous, but maybe that is what makes “Pretty Woman” a great modern-day fairy tale. And rom-com casting doesn’t get much better than Richard Gere and Julia Roberts.

Rating: R, for sexuality and some language.

Where to watch: Amazon Prime.

27. ‘Miss Congeniality’ (2000)

FBI agent Gracie (Sandra Bullock) considers herself “one of the boys.” But when a terrorist threatens to bomb the upcoming Miss America pageant, Gracie must tap into her feminine side and go undercover as a contestant.

Why No. 27? The humor of “Miss Congeniality” is rooted in clever irony. Gracie is a tomboy who must compete in a beauty pageant and falls for a ladies’ man who typically dates girly girls. In shallow ways, the characters break from their molds.

But at her core, Gracie never really changes — she simply opens herself up to new people and experiences.

Rating: PG-13, for sexual references and some violence.

Where to watch: Netflix, Max.

26. ‘Never Been Kissed’ (1999)

A young editor at the Chicago Sun-Times, Josie Gellar (Drew Barrymore), gets sent on an undercover assignment disguised as a high school student. Josie did not have a positive high school experience, but to get a good story, she needs to get involved.

Why No. 26? I will readily admit this movie is kind of problematic. A high school teacher holding secret feelings for his student is creepy. But nothing happens between Josie and her teacher until after he learns she is an adult. The final scene makes up for all the weirdness.

Rating: PG-13 for sex-related material and some drug content.

Where to watch: Starz, Amazon Prime, Hulu.

25. ‘His Girl Friday’ (1940)

New York newspaper editor Walter Burns (Cary Grant) attempts to lure back his ex-wife, investigative reporter Hildy Johnson (Rosalind Russell), with a story she cannot resist.

Why No. 25? The romantic tension between Walter and Hildy is off-the-charts. Every wisecrack hilariously propels the romantic plot.

Rating: G.

Where to watch: Amazon Prime.

24. ‘The Big Sick’ (2017)

Zoe Kazan and Kumail Nanjiani in “The Big Sick.”
Zoe Kazan and Kumail Nanjiani in “The Big Sick.” Nicole Rivelli Lionsgate. | Nicole Rivelli, Nicole Rivelli

Kumail (Kumail Nanjiani) is a Pakistani stand-up comedian who meets Emily (Zoe Kazan) at one of his comedy shows. As their natural chemistry grows, Kumail grows concerned that his parents’ traditional views will get in the way.

But when Emily suffers from a sudden illness that leaves her in a coma, Kumail creates a deep bond with her parents.

Why No. 24? With wit, tragedy and a series of tender sequences, “The Big Sick” effectively highlights how complicated modern relationships can get — without turning viewers off of the idea of romance.

Rating: R, for language and sexual references.

Where to watch: Amazon Prime.

23. ‘Crazy Rich Asians’ (2018)

“Crazy Rich Asians.”CONSTANCE WU as Rachel in Warner Bros. Pictures’, SK Global Entertainment’s and Starlight Culture’s contemporary romantic comedy “Crazy Rich Asians.”
Constance Wu in “Crazy Rich Asians.” | Warner Bros. Pictures

Asian American professor Rachel Chu (Constance Wu) travels home with her longtime boyfriend, Nick (Henry Golding), for his best friend’s wedding in Singapore. It doesn’t take Rachel long to discover Nick comes from one of the wealthiest families in Singapore — and he is the one of the country’s most eligible bachelors.

As single women fight tooth and nail to get Nick’s attention off Rachel, she must decide if her relationship with Nick is worth all the pressure.

Why No. 23? I find it poor judgement on Nick’s part to dump his secret socialite upbringing on Rachel the moment she arrives across the globe to meet his family. But when the cards are stacked against them, the pair prove willing to fight for each other, which makes for a lot of entertaining romance.

Rating: PG-13, for some suggestive content and language.

Where to watch: Hulu.

22. ‘The Philadelphia Story’ (1940)

Philadelphia socialite Tracy Lord (Katharine Hepburn) splits from her husband, C.K. Dexter Haven (Cary Grant), over his burdening work schedule and drinking habits.

As Tracy prepares to marry the wealthy George Kittredge (John Howard), she crosses paths with her ex-husband once again as well as Macaulay Connor (James Stewart), a nosey reporter. She must decide which of the three suitors is best for her.

Why No. 22? It might be the perfect love triangle — er, love quadrant — movie.

Rating: G.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

21. ‘Emma’ (2020)

Emma (Anya Taylor-Joy) fancies herself a matchmaker, but as she meddles with the love lives of her friends, she fails to recognize the romance building right beneath her nose.

Why No. 21? This adaptation of Jane Austen’s “Emma” deploys stunning visuals to bring justice to Austen’s 1815 novel.

Rating: PG, for brief partial nudity.

Where to watch: Peacock.

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20. ‘The Princess Bride’ (1987)

Robin Wright and Cary Elwes in “The Princess Bride.”
Robin Wright and Cary Elwes in “The Princess Bride.” | BYUtv

In this fairytale adventure, Buttercup (Robin Wright) is a beautiful young woman living on a farm in the fictional kingdom Florin. After Buttercup finds her one true love, she is forced into a marriage engagement to the heir of Florin. Her one true love, Wesley (Cary Elwes), must overcome mythical battles to reunite with and save Buttercup.

Why No. 20? “The Princess Bride” has great humor and romance. But it also has fantasy, sword fighting, giants, a mythical kingdom, revenge and a killer script. You would be hard-pressed to find someone who doesn’t enjoy this movie.

Rating: PG, for mild language.

Where to watch: Disney+.

19. ‘While You Were Sleeping’ (1995)

Lucy (Sandra Bullock) is a lonely transit worker in Chicago. Her life gets turned around when she pulls her longtime crush, Peter (Peter Gallagher), off the tracks and saves him from an oncoming train. At the hospital, doctors say Peter is in a coma. Lucy lets Peter’s family believe she is his fiancée, and takes up their offer to stay in their home.

Things get even more complicated as Lucy develops feelings for Peter’s brother, Jack (Bill Pullman).

Why No. 19? From the depths of loneliness, Lucy is swept into a life she only every daydreamed about. She gets her romantic ending, but Lucy is also lovingly embraced by a family — something she longed to have.

Rating: PG, for some language.

Where to watch: Disney+.

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18. ‘To All the Boys I’ve Loved Before’ (2018)

Laura Jean (Lana Condor) is a reserved high school student who mostly keeps to herself. Things change for her when five soul-baring love letters she wrote to her crushes get mysteriously sent out. Her life is thrown in chaos as she attempts to forgo sudden opportunities for romance.

Why No. 18? This movie is tangible evidence that the rom-com is not dead! This is the best rom-com to come out during the last decade and it provides a reminder that romantic tropes (e.g., fake dating schemes) are as effective now as they ever were.

Rating: TV-14 for sexual content and language.

Where to watch: Netflix.

17. ‘A Cinderella Story’ (2004)

Hilary Duff and Chad Michael Murray in “A Cinderella Story.”
Hilary Duff and Chad Michael Murray in “A Cinderella Story.” | Ron Batzdorff

After losing her father in an earthquake, Sam (Hilary Duff) is sentenced to working at her unpleasant stepmother’s diner to earn enough money to attend Princeton. One of the upsides in Sam’s life is her anonymous email relationship with Nomad (Chad Michael Murray).

But when Sam agrees to meet Nomad at the high school dance, she discovers he is the coolest guy at her school. Too intimidated to face him, Sam keeps her identity a secret.

Why No. 17? “A Cinderella Story” wedges the gap between ‘80s/’90s rom-coms and modern ones. It provided us with some of Jennifer Coolidge’s best onscreen moments, Chad Micheal Murray’s peak and “Hear You Me” by Jimmy Eat World.

Rating: PG for mild language.

Where to watch: Rent on Amazon Prime, Apple TV.

16. ‘Hitch’ (2005)

 Will Smith and Eva Mendes in “Hitch.”
Will Smith and Eva Mendes in “Hitch.” | Barry Wetcher, Barry Wetcher

Alex “Hitch” Hitchens (Will Smith) is a dating coach in New York City. Hitch promises to help a blundering client, Albert (Kevin James), win over the girl of his dreams in just three dates. Hitch’s techniques prove to be promising for Albert, but they fail in Hitch’s own love life as he pursues tabloid reporter Sara Melas (Eva Mendes).

Why No. 16? Not too sappy, not too serious,Hitch” offers a near-perfect balance of comedy and romance — even dads will admit they enjoy it.

Rating: PG-13, for some language and sexual references.

Where to watch: Hulu.

15. ‘Four Weddings and a Funeral’ (1994)

Andie MacDowell and Hugh Grant in “Four Weddings and a Funeral.”
Andie MacDowell and Hugh Grant in “Four Weddings and a Funeral.” DESERET NEWS ARCHIVES

Charles (Hugh Grant) blames bad luck for his bleak love life. While attending a wedding, Charles meets a beautiful American, Carrie (Andie MacDowell), and believes his luck may have finally changed. When Carrie returns to the U.S., Charles worries it is the end of something that could have been — until the pair unexpectedly reconnect at a series of weddings.

Why No. 15? Charming, heart-warming and romantic, “Four Weddings and a Funeral” is everything a rom-com should be.

Rating: R, for language and some sexuality.

Where to watch: Amazon Prime, YouTube TV.

14. ‘The Proposal’ (2009)

Sandra Bullock, left, and Betty White star in “The Proposal.”
Sandra Bullock, left, and Betty White star in “The Proposal.” | Kerry Hayes

Margaret Tate (Sandra Bullock) is on the verge of being deported to her native Canada and losing her high-power book editing job. In order to avoid being deported, Margaret says she is engaged to her assistant, Andrew Paxton (Ryan Reynolds). Andrew agrees to the charade on one condition: Margaret visit his dysfunctional family in Alaska.

Why No. 14? “The Proposal” has it all. Enemies to lovers. A fake dating scheme. A third-act declaration of love. Ryan Reynolds.

Rating: PG-13, for sexual content, mild nudity and some language.

Where to watch: Hulu, Disney+.

13. ‘Roman Holiday’ (1953)

Audrey Hepburn and Gregory Peck in “Roman Holiday.”
Audrey Hepburn and Gregory Peck in “Roman Holiday.” | Paramount Pictures

In need of a break from her busy touring schedule, European Princess Ann (Audrey Hepburn) goes out for a night in Rome. Ann falls asleep on a park bench when a sedative she took from her doctor kicks in. Joe Bradley (Gregory Peck), an American reporter, finds her and takes her home.

When Joe discovers Ann is a princess, he bets his editor he can get an interview with her.

Why No. 13? Two hours of pure rom-com bliss featuring Audrey Hepburn and Gregory Peck.

Rating: G.

Where to watch: Amazon Prime.

12. ‘Can’t Buy Me Love’ (1987)

Nerdy high schooler Ronald Miller (Patrick Dempsey) used his life savings to help a popular cheerleader, Cindy (Amanda Peterson), get out of trouble. To pay him back for his help, Cindy agrees to “fake date” Ronald so he can achieve high school popularity. But when Ronald’s loyal best friend gets left behind, he decides popularity isn’t all its cracked up to be.

Why No. 12? Before he was Dr. McDreamy (from “Grey’s Anatomy”), Patrick Dempsey was a lovable dork who proved you really can’t buy love, but love can break social barriers.

Rating: PG-13 for underage smoking and drinking and some language.

Where to watch: Rent on Amazon Prime, YouTube TV, Apple TV.

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11. ‘Notting Hill’ (1999)

Julia Roberts and Hugh Grant in “Notting Hill.”
Julia Roberts and Hugh Grant in “Notting Hill.” | Universal Pictures

William (Hugh Grant) is a bookstore owner in Notting Hill, London. His simple life changes when the glamorous movie star Anna Scott (Julia Roberts) comes into his bookstore. As the pair grow closer to each other, they see how different their lives really are.

Why No. 11? For blessing us with the legendary “I’m also just a girl” line.

Rating: PG-13, for sexual content and brief language.

Where to watch: Netflix, Peacock.

10. ‘13 Going on 30’ (2004)

Jennifer Garner in “13 Going on 30.”
Jennifer Garner in “13 Going on 30.”

Jenna (Jennifer Garner), a middle schooler who can’t figure out how to fit in, wishes to become an adult who has it all figured out. To her surprise, Jenna wakes up as a 30-year-old. It’s no longer 1987, and being an adult proves more complicated than Jenna anticipated.

Why No. 10? A comical reminder that adulthood doesn’t have to suck as long as you retain some youthful flair.

Rating: PG-13.

Where to watch: HBO Max, Netflix.

9. ‘Sixteen Candles’ (1984)

Molly Ringwald and Michael Schoeffling in“Sixteen Candles.”
Molly Ringwald and Michael Schoeffling in“Sixteen Candles.” | Universal City

After her sweet 16 is overlooked because of her older sister’s upcoming wedding, Samantha (Molly Ringwald) faces every possible teenage embarrassment in the book.

To make matters worse, Samantha is hopelessly in love with a handsome senior, Jake (Michael Schoeffling), but the only boy in her entire high school who seems to take any interest in Samantha is Ted (Anthony Michael Hall), a nerdy boy she is constantly shutting down.

Why No. 9? Everything in “Sixteen Candles” leads up to a wholly satisfying ending that is made of every teenager’s dreams.

Rating: PG, for some language, sexual content and alcohol use.

Where to watch: Rent from Amazon Prime, YouTube TV, Apple TV.

8. ‘My Big Fat Greek Wedding’ (2002)

John Corbett Nia Vardalos in “My Big Fat Greek Wedding”
John Corbett Nia Vardalos in “My Big Fat Greek Wedding”

Toula (Nia Vardolos) is still unmarried at 30 and her family, who own a Greek restaurant, begin to worry about her. After taking a new job at a travel agency, Toula falls for Ian (John Corbett), a handsome teacher. Toula’s family must learn to accept Ian, a foreigner, into their big Greek family.

Why No. 8? Toula finds beauty within, which translates into a physical glow-up — but not one the average woman couldn’t aspire to, she mostly brushes her hair and applies some lipgloss.

Also, Ian is into Toula long before she breaks out the lipgloss. His uninhibited love for Toula carries over into the quirky corners of her personality — which offers a gentle reminder true love won’t shy away from your idiosyncrasies.

Rating: PG.

Where to watch: Hulu, Amazon Prime, HBO Max.

7. ‘How to Lose a Guy in 10 Days’ (2003)

Matthew McConaughey as Benjamin Barry and Kate Hudson as Andie Anderson in “How to Lose a Guy in 10 Days.”
Michael Gibson, Paramount Pictures

Andie Anderson (Kate Hudson) is an advice columnist who wants to write a new piece about how to get a man to leave you in 10 days. For her experiment, Andie selects Ben (Matthew McConaughey), a playboy who thinks he can make any women fall in love with him in 10 days. As Andie and Ben fall for each other, their plans backfire.

Why No. 7? This combo of enemies-to-lovers, fake schemes, Matthew McConaughey and Andie’s iconic yellow dress are the ingredients of a near-perfect rom-com.

Rating: PG-13.

Where to watch: Netflix.

6. ‘She’s the Man’ (2006)

Viola Johnson (Amanda Bynes) suffers when her high school cuts the girls soccer team. To keep playing “the beautiful game,” Viola hatches a plan to pose as her older brother, Sebastian, and take his place at a new boarding school. She makes the boarding school’s soccer team with a plan to prove girls can play soccer as well as boys can.

The challenge escalates when Viola begins to fall for her roommate Duke (Channing Tatum), who does not know her real identity.

Why No. 6? Wickedly funny, endlessly quotable and with enough cheesy romance to earn a place in the rom-com genre, “She’s The Man” is a movie you can never watch too many times.

Rating: PG-13 for some sexual material.

Where to watch: Paramount+, Amazon Prime.

5. Clueless’ (1995)

Alicia Silverstone, left, Brittany Murphy and Stacey Dash star in “Clueless” (1995).
Alicia Silverstone, left, Brittany Murphy and Stacey Dash star in “Clueless” (1995). | Paramount Pictures

Cher (Alicia Silverstone) is at the top of her Beverly Hills high school’s social pyramid. To use her popularity for good, Cher befriends a hopelessly awkward new student, Tai (Brittany Murphy), and gives her a makeover.

When Tai becomes more popular than she is, Cher realizes her ex-stepbrother (Paul Rudd) might have been right about how clueless she is — and begins to fall for him.

Why No. 5? I could watch “Clueless” with the sound off and still enjoy myself — it just looks that good.

Rating: PG-13 for some sexual material and some teen use of alcohol and drugs.

Where to watch: Paramount+, Amazon Prime.

4. ‘10 Things I Hate About You’ (1999)

Bianca Stratford (Larisa Oleynik) is desperate to get into the dating scene at her high school, but her strict father will only let her date if her sister, Kat (Julia Stiles), does. Unfortunately for Bianca, Kat has no intentions of dating.

In order to get her way, Bianca schemes to get her sister interested in a handsome new student, Patrick Verona (Heath Ledger).

Why No. 4? The movie has Health Ledger singing “Can’t Take My Eyes Off You.” What’s not to love?

Rating: PG-13 for some sexual material and teenagers using alcohol.

Where to watch: Disney+, Hulu.

3. ‘Pride & Prejudice’ (2005)

Matthew MacFadyen played Mr. Darcy opposite Keira Knightley in the 2005 “Pride and Prejudice.”
Matthew MacFadyen and Keira Knightly in “Pride and Prejudice.” | 1996-98 AccuSoft Inc., All rights reserved

Despite her attraction, Elizabeth Bennet (Keira Knightly) considers the rich Mr. Darcy (Matthew MacFadyen) to be proud and rude. Mr Darcy struggles with the idea of falling in love with Elizabeth, because she is beneath his class. They must both overcome pride and prejudice if they want to make things work.

Why No. 3? Love requires humility. “Pride & Prejudice” uses humor to teach us this romantic truth.

Rating: PG, for some thematic elements.

Where to watch: Peacock.

Related

2. ‘You’ve Got Mail’ (1998)

Meg Ryan and Tom Hanks in 1998’s “You’ve Got Mail.”
Meg Ryan and Tom Hanks in 1998’s “You’ve Got Mail.” | Warner Bros.

Kathleen Kelly (Meg Ryan) is the owner of a small, struggling bookshop in New York. Kathleen hates Joe Fox (Tom Hanks), the owner of a chain bookstore that threatens to shut her shop down. When they meet online anonymously, they develop a romantic virtual relationship despite remaining business rivals.

Why No. 2? “You’ve Got Mail” is pure rom-com perfection. No notes.

Rating: PG.

Where to watch: Hulu, Netflix, HBO Max.

1. ‘When Harry Met Sally’ (1989)

Meg Ryan and Billy Crystal in the 1989 film “When Harry Met Sally.”
Meg Ryan and Billy Crystal in the 1989 film “When Harry Met Sally.” Andy Schwartz Castle Rock Entertainment. | Andy Schwartz, Andy Schwartz

Harry (Billy Crystal) is convinced men and women cannot be just friends — romance will always creep in. Sally (Meg Ryan) disagrees. As a platonic friendship beings developing between the pair, Sally mistakenly thinks she has finally proven her point.

Why No. 1? A combination of the two best tropes (enemies to friends to lovers) starring the queen of rom-coms (Meg Ryan). It’s got the perfect balance of comedy to romance and provides hope to those secretly in love with their best friend. “When Harry Met Sally” is rom-com perfection.

Rating: R, for some language and mild sexuality.

Where to watch: Rent on Apple TV, Amazon Prime. YouTube TV.