Romance Through the Years
by BlackGhost217 | created - 06 Sep 2018 | updated - 19 Apr 2023 | Public- Instant Watch Options
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1. You've Got Mail (1998)
PG | 119 min | Comedy, Drama, Romance
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet, both blissfully unaware that he's trying to put her out of business.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey
Votes: 229,592 | Gross: $115.82M
2. Before Sunrise (1995)
R | 101 min | Drama, Romance
A young man and woman meet on a train in Europe, and wind up spending one evening together in Vienna. Unfortunately, both know that this will probably be their only night together.
Director: Richard Linklater | Stars: Ethan Hawke, Julie Delpy, Andrea Eckert, Hanno Pöschl
Votes: 339,178 | Gross: $5.54M
3. When Harry Met Sally... (1989)
R | 95 min | Comedy, Drama, Romance
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
Director: Rob Reiner | Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Votes: 242,640 | Gross: $92.82M
4. Love, Rosie (2014)
R | 102 min | Comedy, Romance
Rosie and Alex have been best friends since they were 5, so they couldn't possibly be right for one another...or could they? When it comes to love, life and making the right choices, these two are their own worst enemies.
Director: Christian Ditter | Stars: Lily Collins, Sam Claflin, Christian Cooke, Jaime Winstone
Votes: 155,513 | Gross: $0.02M
5. Sleepless in Seattle (1993)
PG | 105 min | Comedy, Drama, Romance
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Ross Malinger, Rita Wilson
Votes: 190,808 | Gross: $126.53M
6. About Time (I) (2013)
R | 123 min | Comedy, Drama, Fantasy
At the age of 21, Tim discovers he can travel in time and change what happens and has happened in his own life. His decision to make his world a better place by getting a girlfriend turns out not to be as easy as you might think.
Director: Richard Curtis | Stars: Domhnall Gleeson, Rachel McAdams, Bill Nighy, Lydia Wilson
Votes: 385,715 | Gross: $15.32M
7. A Walk to Remember (2002)
PG | 101 min | Drama, Romance
Two North Carolina teens, Landon Carter and Jamie Sullivan, are thrown together after Landon gets into trouble and is sentenced to perform community service.
Director: Adam Shankman | Stars: Mandy Moore, Shane West, Peter Coyote, Daryl Hannah
Votes: 221,339 | Gross: $41.28M
8. Me Before You (2016)
PG-13 | 110 min | Drama, Romance
A girl in a small town forms an unlikely bond with a recently-paralyzed man she's taking care of.
Director: Thea Sharrock | Stars: Emilia Clarke, Sam Claflin, Janet McTeer, Charles Dance
Votes: 287,067 | Gross: $56.25M
9. What If (I) (2013)
PG-13 | 98 min | Comedy, Romance
Wallace, who is burned out from a string of failed relationships, forms an instant bond with Chantry, who lives with her longtime boyfriend. Together, they puzzle out what it means if your best friend is also the love of your life.
Director: Michael Dowse | Stars: Daniel Radcliffe, Zoe Kazan, Megan Park, Adam Driver
Votes: 81,666 | Gross: $3.45M
10. Eternal Sunshine of the Spotless Mind (2004)
R | 108 min | Drama, Romance, Sci-Fi
When their relationship turns sour, a couple undergoes a medical procedure to have each other erased from their memories forever.
Director: Michel Gondry | Stars: Jim Carrey, Kate Winslet, Tom Wilkinson, Gerry Robert Byrne
Votes: 1,077,709 | Gross: $34.40M
11. A Knight's Tale (2001)
PG-13 | 132 min | Action, Adventure, Romance
After his master dies, a peasant squire, fueled by his desire for food and glory, creates a new identity for himself as a knight.
Director: Brian Helgeland | Stars: Heath Ledger, Mark Addy, Rufus Sewell, Shannyn Sossamon
Votes: 201,656 | Gross: $56.57M
12. Bicentennial Man (1999)
PG | 132 min | Drama, Romance, Sci-Fi
An android endeavors to become human as he gradually acquires emotions.
Director: Chris Columbus | Stars: Robin Williams, Embeth Davidtz, Sam Neill, Oliver Platt
Votes: 124,655 | Gross: $58.22M
13. The Butterfly Effect (2004)
R | 113 min | Drama, Sci-Fi, Thriller
Evan Treborn suffers blackouts during significant events of his life. As he grows up, he finds a way to remember these lost memories and a supernatural way to alter his life by reading his journal.
Directors: Eric Bress, J. Mackye Gruber | Stars: Ashton Kutcher, Amy Smart, Melora Walters, Elden Henson
Votes: 521,029 | Gross: $57.94M
14. Titanic (1997)
PG-13 | 194 min | Drama, Romance
A seventeen-year-old aristocrat falls in love with a kind but poor artist aboard the luxurious, ill-fated R.M.S. Titanic.
Director: James Cameron | Stars: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates
Votes: 1,280,028 | Gross: $659.33M
15. 50 First Dates (2004)
PG-13 | 99 min | Comedy, Drama, Romance
Henry Roth is a man afraid of commitment until he meets the beautiful Lucy. They hit it off and Henry think he's finally found the girl of his dreams until discovering she has short-term memory loss and forgets him the next day.
Director: Peter Segal | Stars: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin
Votes: 382,055 | Gross: $120.91M
16. Silver Linings Playbook (2012)
R | 122 min | Comedy, Drama, Romance
After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.
Director: David O. Russell | Stars: Bradley Cooper, Jennifer Lawrence, Robert De Niro, Jacki Weaver
Votes: 742,618 | Gross: $132.09M
17. Chocolat (2000)
PG-13 | 121 min | Drama, Romance
A French woman and her young daughter open up a chocolate shop in a small remote village that shakes up the rigid morality of the community.
Director: Lasse Hallström | Stars: Juliette Binoche, Johnny Depp, Judi Dench, Alfred Molina
Votes: 201,933 | Gross: $71.51M
18. Flipped (I) (2010)
PG | 90 min | Comedy, Drama, Romance
Two eighth-graders start to have feelings for each other despite being total opposites.
Director: Rob Reiner | Stars: Madeline Carroll, Callan McAuliffe, Rebecca De Mornay, Anthony Edwards
Votes: 97,440 | Gross: $1.75M
19. Serendipity (2001)
PG-13 | 90 min | Comedy, Romance
A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together.
Director: Peter Chelsom | Stars: John Cusack, Kate Beckinsale, Jeremy Piven, Bridget Moynahan
Votes: 121,335 | Gross: $50.29M
20. The Vow (2012)
PG-13 | 104 min | Drama, Romance
A car accident puts Paige in a coma, and when she wakes up with severe memory loss, her husband Leo works to win her heart again.
Director: Michael Sucsy | Stars: Rachel McAdams, Channing Tatum, Sam Neill, Jessica Lange
Votes: 204,897 | Gross: $125.01M
21. Me and Earl and the Dying Girl (2015)
PG-13 | 105 min | Comedy, Drama, Romance
High schooler Greg, who spends most of his time making parodies of classic movies with his co-worker Earl, finds his outlook forever altered after befriending a classmate who has just been diagnosed with cancer.
Director: Alfonso Gomez-Rejon | Stars: Thomas Mann, RJ Cyler, Olivia Cooke, Nick Offerman
Votes: 138,260 | Gross: $6.74M
22. 500 Days of Summer (2009)
PG-13 | 95 min | Comedy, Drama, Romance
After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.
Director: Marc Webb | Stars: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloë Grace Moretz
Votes: 557,764 | Gross: $32.39M
23. The Big Sick (2017)
R | 120 min | Comedy, Drama, Romance
Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings.
Director: Michael Showalter | Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano
Votes: 143,556 | Gross: $42.87M
24. Shallow Hal (2001)
PG-13 | 114 min | Comedy, Drama, Fantasy
A shallow man falls in love with a 300-pound woman because of her inner beauty.
Directors: Bobby Farrelly, Peter Farrelly | Stars: Jack Black, Gwyneth Paltrow, Jason Alexander, Joe Viterelli
Votes: 144,746 | Gross: $70.84M
25. She's the Man (2006)
PG-13 | 105 min | Comedy, Romance, Sport
When her brother decides to ditch for a couple weeks, Viola heads over to his elite boarding school, disguised as him, and proceeds to fall for his school's star soccer player, and soon learns she's not the only one with romantic troubles.
Director: Andy Fickman | Stars: Amanda Bynes, Laura Ramsey, Channing Tatum, Vinnie Jones
Votes: 175,749 | Gross: $2.34M
26. How to Lose a Guy in 10 Days (2003)
PG-13 | 116 min | Comedy, Romance
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.
Director: Donald Petrie | Stars: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Votes: 269,881 | Gross: $105.81M
27. What Women Want (2000)
PG-13 | 127 min | Comedy, Fantasy, Romance
A cocky, chauvinistic advertising executive magically acquires the ability to hear what women are thinking.
Director: Nancy Meyers | Stars: Mel Gibson, Helen Hunt, Marisa Tomei, Alan Alda
Votes: 222,289 | Gross: $182.81M
28. Just Like Heaven (2005)
PG-13 | 95 min | Comedy, Drama, Fantasy
A lonely landscape architect falls for the spirit of the beautiful woman who used to live in his new apartment.
Director: Mark Waters | Stars: Reese Witherspoon, Mark Ruffalo, Donal Logue, Dina Spybey-Waters
Votes: 117,330 | Gross: $48.32M
29. Larry Crowne (2011)
PG-13 | 98 min | Comedy, Drama, Romance
After losing his job, a middle-aged man reinvents himself by going back to college.
Director: Tom Hanks | Stars: Tom Hanks, Julia Roberts, Sarah Mahoney, Roxana Ortega
Votes: 70,818 | Gross: $35.61M
30. Before Sunset (2004)
R | 80 min | Drama, Romance
Nine years after Jesse and Celine first met, they encounter each other again on the French leg of Jesse's book tour.
Director: Richard Linklater | Stars: Ethan Hawke, Julie Delpy, Vernon Dobtcheff, Louise Lemoine Torrès
Votes: 287,737 | Gross: $5.82M
31. It's a Boy Girl Thing (2006)
PG-13 | 95 min | Comedy, Fantasy, Romance
Sworn enemies find themselves in each other's bodies, and use this to ruin each other's lives.
Director: Nick Hurran | Stars: Samaire Armstrong, Kevin Zegers, Sherry Miller, Robert Joy
Votes: 42,816
32. What Happens in Vegas (2008)
PG-13 | 99 min | Comedy, Romance
A man and a woman are compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Director: Tom Vaughan | Stars: Cameron Diaz, Ashton Kutcher, Rob Corddry, Lake Bell
Votes: 187,837 | Gross: $80.28M
33. Intolerable Cruelty (2003)
PG-13 | 100 min | Comedy, Crime, Romance
Miles, a high-profile divorce lawyer, wins a case for his rich but adulterous client Rex Rexroth. But Rex's ex-wife, Marylin, who is no saint and is a gold-digger, plots to take revenge on Miles.
Directors: Joel Coen, Ethan Coen | Stars: George Clooney, Catherine Zeta-Jones, Billy Bob Thornton, Geoffrey Rush
Votes: 101,836 | Gross: $35.33M
34. Addicted to Love (1997)
R | 100 min | Comedy, Romance
Maggie's and Sam's former partners are in love; she wants revenge and he wants his lost love back, so they work together to break up the happy couple.
Director: Griffin Dunne | Stars: Meg Ryan, Matthew Broderick, Kelly Preston, Tchéky Karyo
Votes: 25,723 | Gross: $34.66M
35. The Heartbreak Kid (2007)
R | 116 min | Comedy, Romance
A newly wed man who believes he's just gotten hitched to the perfect woman encounters another lady on his honeymoon.
Directors: Bobby Farrelly, Peter Farrelly | Stars: Ben Stiller, Michelle Monaghan, Malin Akerman, Jerry Stiller
Votes: 96,535 | Gross: $36.79M
36. Along Came Polly (2004)
PG-13 | 90 min | Comedy, Romance
A buttoned-up newlywed finds his strictly organized life descend into chaos when he falls in love with an old classmate.
Director: John Hamburg | Stars: Ben Stiller, Jennifer Aniston, Debra Messing, Philip Seymour Hoffman
Votes: 143,632 | Gross: $88.10M
37. Just Go with It (2011)
PG-13 | 117 min | Comedy, Romance
On a weekend trip to Hawaii, a plastic surgeon convinces his loyal assistant to pose as his soon-to-be-divorced wife in order to cover up a careless lie he told to his much-younger girlfriend.
Director: Dennis Dugan | Stars: Adam Sandler, Jennifer Aniston, Brooklyn Decker, Nicole Kidman
Votes: 265,407 | Gross: $103.03M
38. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 385,058 | Gross: $38.18M
39. Her (2013)
R | 126 min | Drama, Romance, Sci-Fi
In a near future, a lonely writer develops an unlikely relationship with an operating system designed to meet his every need.
Director: Spike Jonze | Stars: Joaquin Phoenix, Amy Adams, Scarlett Johansson, Rooney Mara
Votes: 669,404 | Gross: $25.57M
40. French Kiss (1995)
PG-13 | 111 min | Comedy, Drama, Romance
A woman flying to France to confront her straying fiance gets into trouble when the charming crook seated next to her uses her for smuggling.
Director: Lawrence Kasdan | Stars: Meg Ryan, Kevin Kline, Timothy Hutton, Jean Reno
Votes: 52,980 | Gross: $38.90M
41. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 342,164 | Gross: $116.09M
42. Pretty Woman (1990)
R | 119 min | Comedy, Romance
A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love.
Director: Garry Marshall | Stars: Richard Gere, Julia Roberts, Jason Alexander, Laura San Giacomo
Votes: 362,081 | Gross: $178.41M
43. Roxanne (1987)
PG | 107 min | Comedy, Romance
The large-nosed C.D. Bales is in love with the beautiful Roxanne; she falls for his personality but another man's looks.
Director: Fred Schepisi | Stars: Steve Martin, Daryl Hannah, Rick Rossovich, Shelley Duvall
Votes: 47,669 | Gross: $40.05M
44. The Proposal (I) (2009)
PG-13 | 108 min | Comedy, Drama, Romance
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.
Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson
Votes: 360,184 | Gross: $163.96M
45. Just Friends (I) (2005)
PG-13 | 96 min | Comedy, Romance
While visiting his hometown during Christmas, a man comes face-to-face with his old high-school crush and best friend--a woman whose rejection of him turned him into a ferocious womanizer.
Director: Roger Kumble | Stars: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein
Votes: 127,260 | Gross: $32.62M
46. Two Weeks Notice (2002)
PG-13 | 101 min | Comedy, Romance
A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him.
Director: Marc Lawrence | Stars: Sandra Bullock, Hugh Grant, Alicia Witt, Dana Ivey
Votes: 125,917 | Gross: $93.35M
47. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,538 | Gross: $55.47M
48. City of Angels (1998)
PG-13 | 114 min | Drama, Fantasy, Romance
An angel on Earth, a doctor unable to believe, a patient with a secret, a love story made in Heaven.
Director: Brad Silberling | Stars: Nicolas Cage, Meg Ryan, Andre Braugher, Dennis Franz
Votes: 127,753 | Gross: $78.69M
49. Ruby Sparks (2012)
R | 104 min | Comedy, Drama, Fantasy
A novelist struggling with writer's block finds romance in a most unusual way: by creating a female character he thinks will love him, then willing her into existence.
Directors: Jonathan Dayton, Valerie Faris | Stars: Paul Dano, Zoe Kazan, Annette Bening, Antonio Banderas
Votes: 105,425 | Gross: $2.54M
50. The Best of Me (2014)
PG-13 | 118 min | Drama, Romance
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.
Director: Michael Hoffman | Stars: James Marsden, Michelle Monaghan, Luke Bracey, Liana Liberato
Votes: 77,424 | Gross: $26.76M
51. The First Time (I) (2012)
PG-13 | 95 min | Comedy, Drama, Romance
A shy senior and a down-to-earth junior fall in love over one weekend.
Director: Jonathan Kasdan | Stars: Dylan O'Brien, Britt Robertson, Victoria Justice, James Frecheville
Votes: 73,617 | Gross: $0.02M
52. He's Just Not That Into You (2009)
PG-13 | 129 min | Comedy, Drama, Romance
This Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior.
Director: Ken Kwapis | Stars: Ginnifer Goodwin, Jennifer Aniston, Jennifer Connelly, Morgan Lily
Votes: 182,203 | Gross: $93.95M
53. Love Wedding Repeat (2020)
TV-MA | 100 min | Comedy, Romance
While trying to make his sister's wedding day go smoothly, Jack finds himself juggling an angry ex-girlfriend, an uninvited guest with a secret, a misplaced sleep sedative, and the girl who got away in alternate versions of the same day.
Director: Dean Craig | Stars: Sam Claflin, Olivia Munn, Freida Pinto, Eleanor Tomlinson
Votes: 22,236
54. Yesterday (III) (2019)
PG-13 | 116 min | Comedy, Fantasy, Music
A struggling musician realizes he's the only person on Earth who can remember The Beatles after waking up in an alternate reality where they never existed.
Director: Danny Boyle | Stars: Himesh Patel, Lily James, Sophia Di Martino, Ellise Chappell
Votes: 167,663 | Gross: $73.29M
55. Love Actually (2003)
R | 135 min | Comedy, Drama, Romance
Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.
Director: Richard Curtis | Stars: Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney
Votes: 531,441 | Gross: $59.70M
56. Little Things (2016– )
TV-MA | 16 min | Comedy, Romance
A cohabiting couple in their 20s navigate the ups and downs of work, modern-day relationships and finding themselves in contemporary Mumbai.
Stars: Dhruv Sehgal, Mithila Palkar, Navni Parihar, Rijul Rajpal
Votes: 7,522
57. Trying (2020–2024)
TV-14 | 30 min | Comedy, Drama, Romance
All Jason and Nikki want is a baby, but it's the one thing they just can't have. So, they decide to adopt. With their dysfunctional friends, screwball family and chaotic lives will the adoption panel think they're ready to be parents?
Stars: Rafe Spall, Esther Smith, Sian Brooke, Oliver Chris
Votes: 11,118
58. Career Opportunities (1991)
PG-13 | 83 min | Comedy, Romance
Jim is the dorky son of a local cement contractor who lives at home and has no direction. Josie is the gorgeous daughter of a wealthy businessman who dreams of leaving town. They find they have a lot in common.
Director: Bryan Gordon | Stars: Frank Whaley, Jennifer Connelly, Dermot Mulroney, Kieran Mulroney
Votes: 17,396 | Gross: $11.34M
59. Always Be My Maybe (2019)
PG-13 | 101 min | Comedy, Romance
Everyone assumed that Sasha and Marcus would wind up together, except for Sasha and Marcus. Reconnecting after 15 years, the two start to wonder--maybe?
Director: Nahnatchka Khan | Stars: Ali Wong, Randall Park, James Saito, Michelle Buteau
Votes: 62,658
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