Best movies like 50 Ways to Leave Your Lover
Last updated March 2024
Looking for movies similar to 50 Ways to Leave Your Lover? Offer your expertise to steer others to films and tv shows you've already seen that might likewise engross them. Assist in widening the community of people alluding videos amongst one another. We value your input!
Plot Summary:
s after an earthquake convince Owen, a writer of hack "as told to" autobiographies, to leave L.A. He burns his bridges telling people what he really thinks, quits his current client (a randy astronaut), and heads for the airport. Waiting for his flight to New York, he sees Val, a friend of his latest ex; they chat, and Owen postpones leaving just to make sure she's not for him.
IMDB Rating: 5.7
IMDB Votes: 1000
Genere: Comedy, Romance
Country: USA
Duration: 95 min
Plot tags: semi serious, sentimental, feel good, humorous, clever, realistic
Best tv shows and movies like 50 Ways to Leave Your Lover (2004):
Similar in 90%
Muffin Top: A Love Story (2014)
Plot Summary:
"Muffin Top: A Love Story" is the story of Suzanne (Cathryn Michon) a Women's Studies Pop Culture professor at Malibu University, who studies images of women in the media for a living, and yet is made insecure by the constant parade of female perfection that is our airbrushed culture. She has been going through IVF treatments to get pregnant by her network executive husband (Diedrich Bader), but discovers on her birthday, that her husband has knocked up his younger, skinnier, co-worker (Haylie Duff) and wants a divorce. Happy Birthday! She goes on to find a more authentic version of who she really is, despite the delights of being suddenly single in Los Angeles, where low self-esteem for women is our number one export to the world.
IMDB Rating: 4.6
IMDB Votes: 754
Genere: Comedy, Romance
Country: USA
Duration: 97 min
Plot tags: humorous, realistic, semi serious, captivating, independent film
Similar in 78%
The Favor (1994)
Plot Summary:
Kathy is married to Peter. Now she can't help but wonder how things could have been if she got together with her old boyfriend, Tom. Being married prevents from doing that so she asks her friend, Emily to go to him and see if she can sleep with him then tell Kathy how it was. When Emily tells Kathy that things were awesome, their friendship suffers, at the same so does Kathy's marriage. Things get even more complicated when Emily learns she's pregnant, and she's not certain if it's Tom's or her boyfriend, Elliot.
IMDB Rating: 5.2
IMDB Votes: 3000
Genere: Comedy, Romance
Country: USA
Duration: 97 min
Plot tags: sexy, light, humorous, entertaining, independent film, offbeat, realistic, talky, semi serious, sex comedy
Similar in 87%
Be My Baby (2007)
Plot Summary:
After dating several cheating husbands who pretended to be single, Rylee devises a scheme for revenge. She gets a married man drunk, convinces him that they slept together, then shows up a year later with a baby and demands money. Her blackmail plan is successful, but then she meets a single man, Max, who wants to be with her and keep the baby.
IMDB Rating: 4.3
IMDB Votes: 347
Genere: Comedy, Romance
Country: USA
Duration: 86 min
Plot tags: feel good, humorous, realistic, semi serious
Similar in 88%
Hairshirt (1998)
Plot Summary:
Danny Reilly (Dean Paras) is a self-obsessed man who, after dumping Renee Weber (Neve Campbell), falls in love again with Corey Wells (Katie Wright). But Renee makes it her mission to see that Danny never falls in love again and sets out for attack when he falls for Corey. Who will get the girl when Danny's constantly talking roomie Tim (Stefan Brogren) falls in love with Corey too?.
IMDB Rating: 4.2
IMDB Votes: 724
Genere: Comedy, Romance
Country: USA
Duration: 89 min
Plot tags: feel good, realistic, humorous, semi serious, independent film
Similar in 76%
Her Minor Thing (2005)
Plot Summary:
Jeana does IT for the Sacramento Fire Department. She and Tom, a self-confident local TV news reporter, are about to go on a cruise to Rio when he lets slip on TV that she is a virgin. It's a slow news week, so this becomes a story: the media pursue Jeana, she breaks up with Tom and wants the tickets or her cruise money back, and Tom can't believe she's serious. Her path crosses that of Paul, a photographer recently arrived from Texas who's also Tom's cameraman; he's had six serious relationships that have ended with his heart broken. A triangle of sorts develops. Will Jeana end up with either man? Will she end up on the cruise? And what about that minor thing?.
IMDB Rating: 5.1
IMDB Votes: 2000
Genere: Comedy, Romance
Country: USA
Duration: 91 min
Plot tags: feel good, humorous, semi serious, realistic, sexy, sex comedy
Similar in 79%
A Business Affair (1994)
Plot Summary:
This is the story of the lovely Kate Swallow and the loves of her life. At the start she is with Alec Bolton, a noted author, who discourages her when she wants to write a novel. Later she is swept off her feet by Alecs publisher, Vanni Corso, and leaves Alec for Vanni. She writes another novel and Vanni tells her he doesn't think the book will sell. Both of their actions are an indication of their vanity and fear of losing her.
IMDB Rating: 5.5
IMDB Votes: 488
Genere: Comedy, Romance
Country: UK, France, Germany, Spain, USA, Romania
Duration: 102 min
Plot tags: humorous, sentimental, thought provoking, captivating, entertaining, realistic, witty, semi serious, independent film
Similar in 81%
Smiling Fish & Goat on Fire (1999)
Plot Summary:
Two brothers share a house in LA's Fairfax district: Tony's a feckless actor, Chris is an accountant. Both are in relationships on rocky ground. As these emotions swirl, Tony meets his US Postal Service letter carrier, a single mom named Kathy who's come to LA from Wyoming with her daughter, a budding actress. Chris meets Anna, an Italian beauty working in the States for a few months wrangling animals on movie sets. Chris also befriends Clive, an aging and crusty man whose longing for his recently-deceased wife is a portrait of true love. Can Clive's example help Chris sort out his love life, and can Tony grow up enough to see the possibilities with Kathy and her daughter?.
IMDB Rating: 7.4
IMDB Votes: 3000
Genere: Comedy, Romance
Country: USA
Duration: 90 min
Plot tags: independent film, touching, offbeat, feel good, humorous, realistic, semi serious, crying, light, thought provoking
Similar in 90%
Luminarias (1999)
Plot Summary:
Welcome to Luminarias-where hot spicy dish gets served up with a Latin twist by four successful friends from East LA...with very discriminating taste in men! When separated divorce attorney Andrea finds herself guilty of falling for her white and Jewish opposing council, her three single friends choose sides in the ongoing and often hilarious debate over race and sex. As they discover just how much negative stereotypes color their relationships with men-and even with each other-it becomes clear that the search for Mr. Right is not exactly black and white!.
IMDB Rating: 5.2
IMDB Votes: 630
Genere: Comedy, Romance
Country: USA
Duration: 100 min
Plot tags: independent film, sentimental, touching, feel good, humorous, realistic, talky, semi serious, hispanic
Similar in 87%
Sam the Man (2001)
Plot Summary:
Before he broke out with the J.D. Salinger-esque Tadpole in 2002, producer-turned-director Gary Winick filmed this little-seen relationship drama. Fisher Stevens stars as the title character, a writer with one novel under his belt who can't seem to deliver the follow-up. Instead, he spends his time compulsively cheating on his photographer girlfriend, Cass (Annabella Sciorra); giving the runaround to his agent, Richard (Ron Rifkin); and trying to keep his landlord, Murray (Luis Guzman), at bay.
IMDB Rating: 4.8
IMDB Votes: 243
Genere: Comedy, Drama, Romance
Country: USA
Duration: 87 min
Plot tags: semi serious, sentimental, sincere, humorous, realistic, suspense, independent film, clever, talky, biting
Similar in 79%
Puccini for Beginners (2006)
Plot Summary:
When her inability to commit leads to a breakup with her girlfriend, opera-loving writer Allegra winds up in the bed of amiable professor Philip. He is so smitten with Allegra that he dumps his lover, Grace (Justin Kirk), and convinces Allegra to continue their affair. When Allegra meets Grace, sparks fly, and she begins a parallel romance, unaware that her new lover is the woman Philip left to be with her.
IMDB Rating: 6.0
IMDB Votes: 2000
Genere: Comedy, Romance
Country: USA
Duration: 82 min
Plot tags: realistic, humorous, witty, semi serious, clever, queer cinema
Similar in 80%
Mango Kiss (2004)
Plot Summary:
"Mango Kiss" is a story about Lou whose world turns upside-down when she falls in love with her best friend Sassafras. They journey to San Francisco and stumble into the wild world of role-playing and non-monogamous S/M dykes. Comedy ensues as these wholesome girls get in over their heads.
IMDB Rating: 4.6
IMDB Votes: 460
Genere: Comedy, Romance
Country: USA
Duration: 84 min
Plot tags: semi serious, humorous, realistic, sexy, independent film, sexual, queer cinema
Similar in 76%
Mr. Jealousy (1997)
Plot Summary:
After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.
IMDB Rating: 6.3
IMDB Votes: 3000
Genere: Comedy, Romance
Country: USA
Duration: 103 min
Plot tags: independent film, clever, humorous, witty, talky, realistic, semi serious, funny, romantic, sexy
Similar in 82%
April's Shower (2003)
Plot Summary:
April's Shower begins with a group of people gathered for a wedding shower for April. At first, it seems to be a normal gathering for such an occasion but, as time goes on, secrets and stories begin to be revealed. Alex is a chef and a maid of honor at April's wedding. She ultimately reveals her true feelings which ends up taking an effect on everybody at the shower.
IMDB Rating: 5.0
IMDB Votes: 718
Genere: Comedy, Romance
Country: USA
Duration: 100 min
Plot tags: sentimental, feel good, humorous, captivating, light, entertaining, touching, realistic, talky, semi serious
Similar in 75%
Forget Paris (1995)
Plot Summary:
Mickey Gordon is a basketball referee who travels to France to bury his father. Ellen Andrews is an American living in Paris who works for the airline he flies on. They meet and fall in love, but their relationship goes through many difficult patches. The story is told in flashback by their friends at a restaurant waiting for them to arrive.
IMDB Rating: 6.5
IMDB Votes: 13000
Genere: Comedy, Romance
Country: USA
Duration: 101 min
Plot tags: sentimental, humorous, light, sweet, intense, touching, realistic, clever, witty, non fiction
Similar in 81%
Cake (2005)
Plot Summary:
A travel writer improves her love life when she becomes an editor for her father's wedding magazine.
IMDB Rating: 4.9
IMDB Votes: 4000
Genere: Comedy, Romance
Country: Canada, USA
Duration: 94 min
Plot tags: touching, feel good, humorous, semi serious, realistic
Similar in 87%
Slightly Single in L.A. (2013)
Plot Summary:
Dale Squire is a hip, quirky, independent single gal living in the glossy city of Los Angeles. After several failed attempts in quasi-relationships, Dale concludes that finding a meaningful relationship in L.A. is impossible. But being anti-social is tough for any young girl in Hollywood. With Jill's frantic wedding right around the corner, Dale finds herself reflecting on the significance of marriage, and the mutual respect needed for a successful relationship. When Zach, a successful heartthrob rock star and old friend of Dale's finds his way back into her life, Dale slowly starts to think that maybe finding love in L.A. is possible - the only problem is that her realization might have come too late, leaving Dale in a silent love triangle, with no way out. Written by Will, Christie.
IMDB Rating: 4.5
IMDB Votes: 1000
Genere: Comedy, Romance
Country: USA, Canada
Duration: 88 min
Plot tags: humorous, sentimental, feel good, semi serious, realistic, independent film
Similar in 80%
Fish Without a Bicycle (2003)
Plot Summary:
Comedy - Julianna (Jenna Mattison) is a struggling actress in a dead end relationship with Danny (Brad Rowe), a fireman who no longer lights her fire. When she decides to leave him and go "find herself" she ends up falling in love with an egotistical director, Michael (Bryan Callen), who can barely fit her in between Pilates classes.
IMDB Rating: 4.3
IMDB Votes: 256
Genere: Comedy, Drama, Romance
Country: USA
Duration: 97 min
Plot tags: humorous, captivating, light, emotional, clever, realistic, witty, talky, semi serious, sexual
Similar in 86%
Hey Good Looking! (2006)
Plot Summary:
No overview found.
IMDB Rating: 5.3
IMDB Votes: 838
Genere: Comedy, Romance
Country: France, UK, Luxembourg, Belgium
Duration: 85 min
Plot tags: touching, humorous, realistic, semi serious, sexual, sexy
Similar in 80%
The Night We Never Met (1993)
Plot Summary:
Sam has a problem with his roommates: they are disgusting, and don't seem to share his views on responsibility, privacy, and basic hygine. Such is his discomfort with his living arrangements that he agrees to share the occupancy of another flat: he gets two nights a week, the owner (a sleazy frat-boy yuppie named Brian, soon to be married) and Ellen (a would-be painter seeking relief from her boring marriage) each get their seperate nights in the flat. Things go extremely well until Sam and Brian swap nights without telling Ellen, who attributes the "nice" things that happen around the place to the slob Brian, while berating the responsible Sam for his hedonistic lifestyle.
IMDB Rating: 6.0
IMDB Votes: 3000
Genere: Comedy, Romance
Country: USA
Duration: 99 min
Plot tags: offbeat, clever, feel good, humorous, realistic, witty, semi serious, independent film
Similar in 85%
Ceremony (2010)
Plot Summary:
Sam Davis convinces his former best friend to spend a weekend with him to rekindle their friendship at an elegant beachside estate owned by a famous documentary filmmaker. However, it soon becomes clear that Sam is secretly infatuated with his ex, Zoe, who is now the filmmaker’s fiancée, and that his true intention is to thwart their impending nuptials. As Sam’s plan begins to unravel, he is forced to realize how complicated love and friendship can be.
IMDB Rating: 5.4
IMDB Votes: 4000
Genere: Comedy, Romance
Country: USA
Duration: 89 min
Plot tags: sentimental, feel good, semi serious, humorous, realistic, romantic, sexy, artsy, indie film, witty
Similar in 81%
What Love Is (2007)
Plot Summary:
It's Valentine's Day and Tomhas big plans. He's about to get engaged and has a surprise party planned to share the good news with friends. But things take a turn for the worse. Tom returns home only to discover his girlfriend has packed up and left him. Now, instead of a surprise party, the surprise is on Tom. Fortunately, his friends are there to help him make sense of it all.
IMDB Rating: 5.2
IMDB Votes: 1000
Genere: Comedy, Romance
Country: USA
Duration: 93 min
Plot tags: humorous, realistic, talky, witty, semi serious, sexual, sexy
Similar in 77%
Never Again (2001)
Plot Summary:
A man and a woman who have pledged never to fall in love again meet in a gay bar.
IMDB Rating: 6.2
IMDB Votes: 967
Genere: Comedy, Romance
Country: USA
Duration: 98 min
Plot tags: sentimental, touching, humorous, witty, semi serious, romantic, independent film, romantic comedy, realistic
Similar in 81%
BachelorMan (2003)
Plot Summary:
In these times of enlightened sexual politics, Ted Davis is a scoring machine. He's got the rap, the charm and his little black book weighs several pounds. Ted has become a guru to his buddies who can only aspire in awe to his greatness. This is a man's man, a ladies man, a super-hero: He's Ted Davis: "BachelorMan".
IMDB Rating: 4.6
IMDB Votes: 466
Genere: Comedy, Romance
Country: USA
Duration: 90 min
Plot tags: feel good, humorous, realistic, semi serious
Similar in 84%
Bridal Fever (2008)
Plot Summary:
It’s a race to the altar when a steamy romance novelist with a long line of torrid romances – and ex-husbands – sets out to help a single woman ditch her bridesmaid dresses once and for all.
IMDB Rating: 5.6
IMDB Votes: 566
Genere: Romance
Country: USA
Duration: 88 min
Plot tags: feel good, semi serious, sentimental, touching, humorous, realistic
Similar in 78%
Four Play (2001)
Plot Summary:
This romantic comedy deals with the fleeting attractions between men and women. When American Ben arrives in London to become a writer on a well-known sitcom, he never dreamed that he would end up in a complex love quadrangle. Sitcom star Carly is married to show producer Allen. French make-up artist Fiona is single, as is Ben. Though Carly quickly develops a crush on Ben, she decides that Fiona w.
IMDB Rating: 4.8
IMDB Votes: 697
Genere: Comedy
Country: USA, UK
Duration: 87 min
Plot tags: semi serious, sentimental, clever, humorous, realistic, sex comedy, independent film
Similar in 90%
Pipe Dream (2002)
Plot Summary:
A lonely plumber poses as a movie director to meet women, and the writer whose script he's stolen builds on his ruse to get her movie made.
IMDB Rating: 6.0
IMDB Votes: 1000
Genere: Comedy, Romance
Country: USA
Duration: 91 min
Plot tags: feel good, humorous, realistic, witty, clever, semi serious, independent film
Similar in 90%
Purple Violets (2007)
Plot Summary:
Patti Petalson is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first love Brian Callahan, a successful crime novelist. Kate is Patti's best friend since college; she's a tough-talking schoolteacher who plays therapist to all Patti's problems, while she's got a few of her own.
IMDB Rating: 6.4
IMDB Votes: 3000
Genere: Comedy, Drama, Romance
Country: USA
Duration: 103 min
Plot tags: sentimental, humorous, realistic, semi serious
Similar in 78%
I Hate Valentine's Day (2009)
Plot Summary:
A love story set in Manhattan, where a florist who abides by a strict five-date-limit with any man finds herself wanting more with the new restaurateur in town.
IMDB Rating: 4.7
IMDB Votes: 9000
Genere: Comedy, Romance
Country: USA
Duration: 98 min
Plot tags: romantic, feel good, semi serious, humorous, realistic, sincere, sweet, touching, romantic comedy, exciting
Similar in 77%
Amy's Orgasm (2001)
Plot Summary:
Amy is a single 29 year old Jewish woman. She wrote a successful self-help book about how women can't truly be in love and experience "mental orgasm." Her parents and acquaintances always try to give her advice. Eventually, she breaks her celibacy and starts dating a radio shock jock, who is known for hitting on his bimbo guests. Of all men, will she find in him the true love she never believed in.
IMDB Rating: 5.3
IMDB Votes: 2000
Genere: Comedy, Romance
Country: USA
Duration: 87 min
Plot tags: sexy, ironic, witty, humorous, semi serious, independent film, clever, talky, realistic, sex comedy
Similar in 80%
Three Can Play That Game (2007)
Plot Summary:
Shanté Smith has moved to Atlanta where she's the Love Doctor, helping women get their men to the altar. Tiffany calls her after she catches her boyfriend, Byron, in a clinch with his boss, Carla, just after he wins a competition similar to "The Apprentice." Shanté initiates a five-step program for Tiffany while Byron seeks advice from his best friend, Gizzard. The five steps include her meeting his family and her offering and withholding sex; Byron and Gizzard respond with their own strategies. Then, Bryon consults Shanté: has the Love Doctor switched sides? And, what happens if Byron finds out that Tiffany's playing games? Can true love run without a play book?.
IMDB Rating: 4.6
IMDB Votes: 886
Genere: Comedy, Romance
Country: USA
Duration: 90 min
Plot tags: sentimental, semi serious, humorous, realistic, witty, black comedy, clever