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44 Movies to watch when you’re in love

September 1, 2015

Kerry and Sarah 3

{a favorite photo of Kerry and me at the beach a few years ago}

44 movies to watch when you’re in love – Connecticut in Style

One of the most romantic things that my husband has ever done was to ask me if I wanted to watch a movie.

When Kerry and I were first dating, he was living in Indiana and I was here in Connecticut. Due to our careers, we’d only be able to see each other on the weekends – but not every weekend. On the Friday of one of the weekends that we weren’t going to see each other, he called me from his cell phone and asked me if I wanted to watch a movie. My heart leapt because I thought it was a surprise visit and that he was actually at my front door. He wasn’t there, but he did the next best thing. He invited me on a virtual date to watch the same movie at the same time and keep the phone lines open so we could chat during the movie. With ‘movies on demand’ we simultaneously pressed play and watched an old movie that I had never seen before, The Princess Bride. It remains one of our most memorable dates.

If you are in the mood to reminisce about falling in love, here’s a roundup of 44 great Romance-Comedy films. Enjoy!

  1. MV5BMTM2MTI5NzA3MF5BMl5BanBnXkFtZTcwODExNTc0OA@@._V1._SX54_CR0,0,54,74_ Silver Linings Playbook (2012) – 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. With: Bradley Cooper, Jennifer Lawrence, Robert De Niro
  2. MV5BMTYzNjkxMTczOF5BMl5BanBnXkFtZTgwODg5NDc2MjE@._V1._SX54_CR0,0,54,74_ Amélie (2001) – Amelie is an innocent and naive girl in Paris with her own sense of justice. She decides to help those around her and, along the way, discovers love. Director: Jean-Pierre Jeunet. With: Audrey Tautou, Mathieu Kassovitz, Rufus
  3. MV5BMTU0MzQyNTExMV5BMl5BanBnXkFtZTgwMjA0Njk1MDE@._V1._SX54_CR0,0,54,74_ Groundhog Day (1993) – A weatherman finds himself living the same day over and over again. Director: Harold Ramis. With: Bill Murray, Andie MacDowell, Chris Elliott
  4. <Juno, the movie> Juno (2007) – Faced with an unplanned pregnancy, an offbeat young woman makes an unusual decision regarding her unborn child. Director: Jason Reitman With: Ellen Page, Michael Cera, Jennifer Garner
  5. MV5BMTQwMTM2MjE4Ml5BMl5BanBnXkFtZTgwODQ2NTYxMTE@._V1._SX54_CR0,0,54,74_ (1) Life is Beautiful (1997) – When an open-minded Jewish librarian and his son become victims of the Holocaust, he uses a perfect mixture of will, humor and imagination to protect his son from the dangers around their camp. Director: Roberto Benigni. With: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini
  6. MV5BMTg2MjkwMTM0NF5BMl5BanBnXkFtZTcwMzc4NDg2NQ@@._V1._SX54_CR0,0,54,74_ Crazy, Stupid, Love (2011) – A middle-aged husband’s life changes dramatically when his wife asks him for a divorce. He seeks to rediscover his manhood with the help of a newfound friend, Jacob, learning to pick up girls at bars. Director: Glenn Ficarra, John Requa. With: Steve Carell, Ryan Gosling, Julianne Moore
  7. MV5BMTk5MjM4OTU1OV5BMl5BanBnXkFtZTcwODkzNDIzMw@@._V1._SX54_CR0,0,54,74_ (500) Days of Summer (2009) – An offbeat romantic comedy about a woman who doesn’t believe true love exists, and the young man who falls for her. Director: Marc Webb With: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend
  8. MV5BMTUxMzcxNzQzOF5BMl5BanBnXkFtZTcwMzQxNjUyMw@@._V1._SX54_CR0,0,54,74_ Mr. & Mrs. Smith (2005) – A bored married couple is surprised to learn that they are both assassins hired by competing agencies to kill each other. Director: Doug Liman With: Brad Pitt, Angelina Jolie, Adam Brody
  9. MV5BMTY4NjQ5NDc0Nl5BMl5BanBnXkFtZTYwNjk5NDM3._V1._SX54_CR0,0,54,74_ Love Actually (2003) – 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. With: Hugh Grant, Martine McCutcheon, Liam Neeson
  10. MV5BMTU5MzU2MzY2Nl5BMl5BanBnXkFtZTgwOTM4NzMxMDE@._V1._SX54_CR0,0,54,74_ The 40-Year-Old-Virgin (2005) – Goaded by his buddies, a nerdy guy who’s never “done the deed” only finds the pressure mounting when he meets a single mother. Director: Judd Apatow .With: Steve Carell, Catherine Keener, Paul Rudd
  11. MV5BMTU1Njk0ODEwOF5BMl5BanBnXkFtZTYwMzA3ODc2._V1._SX54_CR0,0,54,74_ Knocked Up (2007) – For fun loving party animal Ben Stone, the last thing he ever expected was for his one night stand to show up on his doorstep eight weeks later to tell him she’s pregnant. Director: Judd Apatow. With: Seth Rogen, Katherine Heigl, Paul Rudd
  12. MV5BMTkzMDgyNjQwM15BMl5BanBnXkFtZTgwNTg2Mjc1MDE@._V1._SX54_CR0,0,54,74_ The Princess Bride (1987) – While home sick in bed, a young boy’s grandfather reads him a story called The Princess Bride. Director: Rob Reiner. With: Cary Elwes, Mandy Patinkin, Robin Wright
  13. MV5BMTc4NTUyNzU4MV5BMl5BanBnXkFtZTcwMzcyMTkyMQ@@._V1._SX54_CR0,0,54,74_ Wedding Crashers (2005) – John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary. Director: David Dobkin. With: Owen Wilson, Vince Vaughn, Rachel McAdams
  14. MV5BMTAxNDYxMjg0MjNeQTJeQWpwZ15BbWU3MDcyNTk2OTM@._V1._SX54_CR0,0,54,74_ Tangled (2010) – The magically long-haired Rapunzel has spent her entire life in a tower, but now that a runaway thief has stumbled upon her, she is about to discover the world for the first time, and who she really is. Directors: Nathan Greno, Byron Howard. With: Mandy Moore, Zachary Levi, Donna Murphy
  15. MV5BMjE1MzU1Mjg1OF5BMl5BanBnXkFtZTcwNDc3NDQ2Mw@@._V1._SX54_CR0,0,54,74_ Easy A (2010) – A clean-cut high school student relies on the school’s rumor mill to advance her social and financial standing. Director: Will Gluck. With: Emma Stone, Amanda Bynes, Penn Badgley
  16. MV5BMTkwNTczNTMyOF5BMl5BanBnXkFtZTcwNzUxOTUyMw@@._V1._SX54_CR0,0,54,74_ Scott Pilgrim vs. the World (2010) – Scott Pilgrim must defeat his new girlfriend’s seven evil exes in order to win her heart. Director: Edgar Wright. With: Michael Cera, Mary Elizabeth Winstead, Kieran Culkin
  17. MV5BMTAzNzM3NTM4NDNeQTJeQWpwZ15BbWU4MDgzOTgzMTAx._V1._SX54_CR0,0,54,74_ There’s Something About Mary (1998) – A man gets a chance to meet up with his dream girl from highschool, even though his date with her back then was a complete disaster. Directors: Bobby Farrelly, Peter Farrelly. With: Ben Stiller, Cameron Diaz, Matt Dillon
  18. MV5BNTI4ODQ1MzAzNV5BMl5BanBnXkFtZTgwMzU4NzMxMDE@._V1._SY74_CR1,0,54,74_ Aladdin (1992) – When a street urchin vies for the love of a beautiful princess, he uses a genie’s magic power to make himself off as a prince in order to marry her. Directors: Ron Clements, John Musker. With: Scott Weinger, Robin Williams, Linda Larkin
  19. MV5BMTEwMTc3NDkzOTJeQTJeQWpwZ15BbWU3MDI4NTAwNzc@._V1._SX54_CR0,0,54,74_ Moonrise Kingdom (2012) – A pair of young lovers flee their New England town, which causes a local search party to fan out to find them. Director: Wes Anderson. With: Jared Gilman, Kara Hayward, Bruce Willis
  20. MV5BMTc0Nzc5MDEzN15BMl5BanBnXkFtZTcwMjc2NTEyMQ@@._V1._SX54_CR0,0,54,74_ As Good as It Gets (1997) – A single mother/waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is in an accident. Director: James L. Brooks. With: Jack Nicholson, Helen Hunt, Greg Kinnear 
  21. MV5BMTYzODgzMjAyM15BMl5BanBnXkFtZTcwMTI3NzI2MQ@@._V1._SX54_CR0,0,54,74_ Forgetting Sarah Marshall (2008) – Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah’s traveling to the same resort as her ex – and she’s bringing along her new boyfriend. Director: Nicholas Stoller. With: Kristen Bell, Jason Segel, Paul Rudd
  22. MV5BMTU1MzY1ODIyNV5BMl5BanBnXkFtZTcwNDU4NTE3Mg@@._V1._SX54_CR0,0,54,74_ The Proposal (2009) – 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. With: Sandra Bullock, Ryan Reynolds, Mary Steenburgen
  23. MV5BMjAyOTMyMzUxNl5BMl5BanBnXkFtZTcwODI4MzE0NA@@._V1._SX54_CR0,0,54,74_ Bridesmaids (2011) – Competition between the maid of honor and a bridesmaid, over who is the bride’s best friend, threatens to upend the life of an out-of-work pastry chef. Director: Paul Feig. With: Kristen Wiig, Maya Rudolph, Rose Byrne
  24. MV5BMTI4MzU5OTc2MF5BMl5BanBnXkFtZTYwNzQxMjc5._V1._SX54_CR0,0,54,74_ 10 Things I Hate About You (1999) – A new kid must find a guy to date the meanest girl in school, the older sister of the girl he has a crush on, who cannot date until her older sister does. Director: Gil Junger. With: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
  25. MV5BMTQ0ODc4MDk4Nl5BMl5BanBnXkFtZTcwMTEzNzgzNA@@._V1._SX54_CR0,0,54,74_ The Graduate (1967) – A disillusioned college graduate finds himself torn between his older lover and her daughter. Director: Mike Nichols. With: Dustin Hoffman, Anne Bancroft, Katharine Ross
  26. MV5BMTMwNTA5ODAxM15BMl5BanBnXkFtZTYwNTQwODU5._V1._SX54_CR0,0,54,74_ Pretty Woman (1990) – 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. With: Richard Gere, Julia Roberts, Jason Alexander
  27. MV5BMTcyMTMzNzE5N15BMl5BanBnXkFtZTcwNzg5NjM5Nw@@._V1._SX54_CR0,0,54,74_ Pitch Perfect (2012) – Beca, a freshman at Barden University, is cajoled into joining The Bellas, her school’s all-girls singing group. Injecting some much needed energy into their repertoire, The Bellas take on their male rivals in a campus competition. Director: Jason Moore. With: Anna Kendrick, Brittany Snow, Rebel Wilson 
  28. MV5BMTQ4MDg5MTE1N15BMl5BanBnXkFtZTgwNDA4NjQxMTE@._V1._SX54_CR0,0,54,74_ Notting Hill (1999) – The life of a simple bookshop owner changes when he meets the most famous film star in the world. Director: Roger Michell. With: Hugh Grant, Julia Roberts, Richard McCabe
  29. MV5BMjc5MDE0NjkxOF5BMl5BanBnXkFtZTcwNzA0NTkyMw@@._V1._SX54_CR0,0,54,74_ Garden State (2004) – A quietly troubled young man returns home for his mother’s funeral after being estranged from his family for a decade.Dir: Zach Braff With: Zach Braff, Peter Sarsgaard, Natalie Portman
  30. MV5BMTY5MjA3MTY2Ml5BMl5BanBnXkFtZTcwNTMzNzYzMw@@._V1._SX54_CR0,0,54,74_ Stranger Than Fiction (2006) – An IRS auditor suddenly finds himself the subject of narration only he can hear: narration that begins to affect his entire life, from his work, to his love-interest, to his death. Director: Marc Forster. With: Will Ferrell, Emma Thompson, Dustin Hoffman
  31. MV5BMTkxNjc2NjQwOF5BMl5BanBnXkFtZTcwMDE2NDU2MQ@@._V1._SX54_CR0,0,54,74_ Jerry Maguire (1996) – When a sports agent has a moral epiphany and is fired for expressing it, he decides to put his new philosophy to the test as an independent with the only athlete who stays with him. Director: Cameron Crowe. With: Tom Cruise, Cuba Gooding Jr., Renée Zellweger
  32. MV5BMzk0NzQxMTM0OV5BMl5BanBnXkFtZTcwMzU4MDYyNQ@@._V1._SY74_CR1,0,54,74_ The Artist (2011) – A silent movie star meets a young dancer, but the arrival of talking pictures sends their careers in opposite directions. Director: Michel Hazanavicius. With: Jean Dujardin, Bérénice Bejo, John Goodman
  33. MV5BMTc0ODI2NDk2OV5BMl5BanBnXkFtZTcwNTIzNDQ4OQ@@._V1._SX54_CR0,0,54,74_ Shakespeare in Love (1998) – A young Shakespeare, out of ideas and short of cash, meets his ideal woman and is inspired to write one of his most famous plays. Director: John Madden. With: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush
  34. MV5BMTEyMzM3NDQyMjJeQTJeQWpwZ15BbWU4MDE4ODY0NjEx._V1._SX54_CR0,0,54,74_ The Goonies (1985) – In order to save their home from foreclosure, a group of misfits set out to find a pirate’s ancient treasure. Director: Richard Donner. With: Sean Astin, Josh Brolin, Jeff Cohen
  35. MV5BMTU4MjI5NTEyNV5BMl5BanBnXkFtZTcwNjQ1NTMzMg@@._V1._SX54_CR0,0,54,74_ I Love You Man (2009) – Friendless Peter Klaven goes on a series of man-dates to find a Best Man for his wedding. But, when his insta-bond with his new B.F.F. puts a strain on his relationship with his fiancée, can the trio learn to live happily ever after? Director: John Hamburg. With: Paul Rudd, Jason Segel, Rashida Jones 
  36. MV5BMTU0Mjg3MzkxOV5BMl5BanBnXkFtZTYwNDU1OTY3._V1._SX54_CR0,0,54,74_ Sideways (2004) – Two men reaching middle age with not much to show but disappointment, embark on a week long road trip through California’s wine country, just as one is about to take a trip down the aisle. Director: Alexander Payne. With: Paul Giamatti, Thomas Haden Church, Virginia Madsen
  37. MV5BNDk0OTM1Mzk3M15BMl5BanBnXkFtZTgwNDg2NjIyMDE@._V1._SX54_CR0,0,54,74_ Big (1998) – When a boy wishes to be big at a magic wish machine, he wakes up the next morning and finds himself in an adult body. Director: Penny Marshall. With: Tom Hanks, Elizabeth Perkins, Robert Loggia
  38. MV5BMjE0ODEwNjM2NF5BMl5BanBnXkFtZTcwMjU2Mzg3NA@@._V1._SX54_CR0,0,54,74_ When Harry Met Sally (1989) – 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. With: Billy Crystal, Meg Ryan, Carrie Fisher
  39. MV5BMTQ2Mzg4MDAzNV5BMl5BanBnXkFtZTgwMjcxNTYxMTE@._V1._SX54_CR0,0,54,74_ About A Boy (2002) – A cynical, immature young man is taught how to act like a grown-up by a little boy. Directors: Chris Weitz, Paul Weitz. With: Hugh Grant, Nicholas Hoult, Toni Collette
  40. MV5BMTc1Mzc1ODMxMF5BMl5BanBnXkFtZTcwNDY1MzU1MQ@@._V1._SX54_CR0,0,54,74_ Definitely, Maybe (2008) – A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter. Director: Adam Brooks. With: Ryan Reynolds, Rachel Weisz, Abigail Breslin
  41. MV5BMTY5ODMyMDY4NF5BMl5BanBnXkFtZTcwNDgwMDEyMQ@@._V1._SX54_CR0,0,54,74_ Chasing Amy (1997) – Holden and Banky are comic book artists. Everything’s going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she’s gay. Director: Kevin Smith. With: Ben Affleck, Joey Lauren Adams, Ethan Suplee
  42. MV5BOTcwMDMxMjg2NF5BMl5BanBnXkFtZTYwNzg0MDc3._V1._SX54_CR0,0,54,74_ Punch Drunk Love (2002) – A psychologically troubled novelty supplier is nudged towards a romance with an English woman, all the while being extorted by a phone-sex line run by a crooked mattress salesman, and purchasing stunning amounts of pudding. Director: Paul Thomas Anderson. With: Adam Sandler, Emily Watson, Philip Seymour Hoffman
  43. MV5BMTUwODg2OTA4OF5BMl5BanBnXkFtZTgwOTE5MTE4MzE@._V1._SX54_CR0,0,54,74_ Focus (2015) – In the midst of veteran con man Nicky’s latest scheme, a woman from his past – now an accomplished femme fatale – shows up and throws his plans for a loop. Directors: Glenn Ficarra, John Requa. With: Will Smith, Margot Robbie, Rodrigo Santoro
  44. MV5BMjAwMzc4MDgxNF5BMl5BanBnXkFtZTYwNjUwMzE3._V1._SX54_CR0,0,54,74_ 50 First Dates (2004) – Henry Roth is a man afraid of commitment up until he meets the beautiful Lucy. They hit it off and Henry think he’s finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the very next day. Director: Peter Segal. With: Adam Sandler, Drew Barrymore, Rob Schneider

 

{Movie Information and Description Credit: IMDb}

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