Most Similar Movies to I Hate Valentine's Day (2009)
If you are looking for movies like I Hate Valentine's Day (2009), you might like movies tagged with keyword : romance, comedy, romantic comedy, dating, relationships, indie film, new york, female lead, male lead, cultural clash, single life, humor, lighthearted, modern love, urban life, personal growth, emotional struggle, independent woman, male perspective, female director .
The Ugly Truth (2009), Trainwreck (2015), Love & Sex (2000), Set It Up (2018), How to Lose a Guy in 10 Days (2003), Dorfman in Love (2011), You Can't Hurry Love (1988) ... Let's take a look at the following list...

The Ugly Truth (2009)
An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man.
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Trainwreck (2015)
Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.
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Love & Sex (2000)
While writing a story on modern dating, a journalist (Famke Janssen) reflects on her own bad choices stemming from her fear of commitment.
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Set It Up (2018)
Two corporate executive assistants hatch a plan to match-make their two bosses.
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How to Lose a Guy in 10 Days (2003)
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. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made.
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Dorfman in Love (2011)
A young woman (Sara Rue) gets an opportunity to transform her messy life when she volunteers to cat-sit at an unrequited love's downtown Los Angeles loft.
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You Can't Hurry Love (1988)
A comedy of a guy who is told the only way to be successful in LA is by "pretending to be someone else." Through a series of dates at a video dating service, he learns that isn't the case, and that it's better to be yourself, rather than what you think others want you to be. Based on the comedy short film "Video Valentino."
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Half Magic (2018)
After a day at work with a male chauvinistic boss, Honey joins a feminist pussy seminar and makes 2 friends. They support each other in their relationships with men etc.
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And Then Came Love (2007)
Julie, a successful magazine columnist, opens Pandora's Box and seeks out the anonymous sperm donor who fathered her young son.
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Annie Hall (1977)
Neurotic New York comedian Alvy Singer falls in love with the ditzy Annie Hall.
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Love and Anarchy (2020)
A married consultant and a young IT technician assign each other challenges in a flirtatious game.
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Hitch (2005)
While helping his latest client woo the woman of his dreams, a professional "date doctor" finds that his game doesn't quite work on the gossip columnist with whom he's smitten.
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Sleeping with Other People (2015)
A good-natured womanizer and a serial cheater form a platonic relationship that helps reform them in ways, while a mutual attraction sets in.
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Kissing Jessica Stein (2001)
A woman searching for the perfect man instead discovers the perfect woman.
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Watching the Detectives (2007)
A film noir buff to the extreme is given a taste of his own medicine and has his life turned upside down by a kooky femme fatale with a big adventure in mind. Sometimes love is stranger than fiction.
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Talk of the Town (1995)
Monika, the host of a daily radio call-in show on the verge of beco- ming a thirtysomething, has almost given up all hopes of finding the man of her dreams when her gay brother convinces her to try it one last time -- via a contact advertisement. Suprisingly, she finds some- one she instantly falls in love with, only to find out that her "Mr. Perfect" is already marri...Read all
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Never Again (2001)
Two people who have pledged never to fall in love again then discover each other in a gay bar.
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Love Is in the Air (2013)
Antoine is a lawyer living in New York. On his way back to France for the final round of a job interview, Antoine finds himself sitting right next to his ex-girlfriend Julie. With a seven-hour flight ahead of them, they are going to have to speak to each other.
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