Most Similar Movies to Down with Love (2003)
If you are looking for movies like Down with Love (2003), you might like movies tagged with keyword : romantic comedy, retro style, career woman, lighthearted humor, female independence, male perspective, over-the-top acting, social satire, female empowerment, emotional growth, battle of the sexes, 1960s setting, new york setting, gender stereotypes .
The Matchbreaker (2016), Love and Anarchy (2020), The Ugly Truth (2009), You Can't Hurry Love (1988), Pyaar Ka Punchnama (2011), Adam's Rib (1949), The Names of Love (2010) ... Let's take a look at the following list...

The Matchbreaker (2016)
A rich merchant, Antonio is depressed for no good reason, until his good friend Bassanio comes to tell him how he's in love with Portia. Portia's father has died and left a very strange will: only the man that picks the correct casket out of three (silver, gold, and lead) can marry her. Bassanio, unfortunately, is strapped for cash with which to go wooing, and Antonio...Read all
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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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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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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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Pyaar Ka Punchnama (2011)
After falling in love, three room-mates experience changes in their lives.
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Adam's Rib (1949)
Domestic and professional tensions mount when a husband and wife work as opposing lawyers in a case involving a woman who shot her husband.
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The Names of Love (2010)
A young, extroverted left-wing activist who sleeps with her political opponents to convert them to her cause is successful until she meets her match.
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Take a Letter, Darling (1942)
A struggling painter takes a job as a secretary to a female advertising executive. While working to obtain an account from a tobacco company, they end up falling in love.
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Two Ninas (1999)
Just about to leave New York City to go home to Maine, a man meets and falls for two women (Cara Buono, Amanda Peet) named Nina.
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Pyaar Ke Side Effects (2006)
A commitment-phobe agrees to marry his girlfriend, setting in motion a series of hilarious mishaps that has him questioning what he got himself into.
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Think Like a Man (2012)
Four friends conspire to turn the tables on their women when they discover the ladies have been using Steve Harvey's relationship advice against them.
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It's Complicated (2009)
When attending their son's college graduation, a couple reignite the spark in their relationship. But the complicated fact is they're divorced and he's remarried.
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Friends with Benefits (2011)
A young man and woman decide to take their friendship to the next level without becoming a couple, but soon discover that adding sex only leads to complications.
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Bridget Jones's Baby (2016)
Bridget's focus on single life and her career is interrupted when she finds herself pregnant, but with one hitch ... she can only be fifty percent sure of the identity of her baby's father.
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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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The Rebound (2009)
In New York City, a single mom captivates her new neighbor, a much younger man.
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Luka Chuppi (2019)
Pretending to be married in order to cohabitate, a small-town couple lands in endless awkward situations to hide the truth from their orthodox families.
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That Old Feeling (1997)
A bride's divorced parents find their old feelings for each other during the wedding reception and over the course of the next few days upsetting the newlywed's honeymoon.
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