Cynical Romantic Comedies

My favorite cynical but funny romance stories. Some movies are funny but sometimes romance can be a little sad...
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1.
Garden State (2004)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A quietly troubled young man returns home for his mother's funeral after being estranged from his family for a decade. (102 mins.)
Director: Zach Braff
 
2.
Knocked Up (2007)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
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 with his child. (129 mins.)
Director: Judd Apatow
 
3.
Juno (2007)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Faced with an unplanned pregnancy, an offbeat young woman makes an unusual decision regarding her unborn child. (96 mins.)
Director: Jason Reitman
 
4.
Waitress (2007)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness. (108 mins.)
Director: Adrienne Shelly
 
5.
Love & Other Drugs (2010)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A young woman suffering from Parkinson's befriends a drug rep working for Pfizer in 1990s Pittsburgh. (112 mins.)
Director: Edward Zwick
 
6.
Marley & Me (2008)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A family learns important life lessons from their adorable, but naughty and neurotic dog. (115 mins.)
Director: David Frankel
 
7.
Spread (2009)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
A sex comedy centered on a serial womanizer and his jilted lover. (97 mins.)
Director: David Mackenzie
 
8.
The Last Kiss (2006)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Michael and Jenna, having been a couple for three years, want to get married and start a family. These... (115 mins.)
Director: Tony Goldwyn
 
9.
Punch-Drunk Love (2002)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
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. (95 mins.)
 
10.
(500) Days of Summer (2009)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her. (95 mins.)
Director: Marc Webb
 
11.
He's Just Not That Into You (2009)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
The Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior. (129 mins.)
Director: Ken Kwapis
 
12.
Wild Target (2010)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A hitman tries to retire but a beautiful thief may change his plans. (98 mins.)
Director: Jonathan Lynn
 
13.
YPF (2007)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
On a Tuesday night, five couples have separate sexual adventures. (87 mins.)
Director: Martin Gero
 
14.
How to Lose a Guy in 10 Days (2003)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
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. (116 mins.)
Director: Donald Petrie
 
15.
It's Complicated (2009)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
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. (120 mins.)
Director: Nancy Meyers
 
16.
50/50 (2011)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
Inspired by a true story, a comedy centered on a 27-year-old guy who learns of his cancer diagnosis, and his subsequent struggle to beat the disease. (100 mins.)
Director: Jonathan Levine
 
17.
Not Suitable for Children (2012)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
A young playboy who learns he has one month until he becomes infertile sets out to procreate as much as possible. (97 mins.)
Director: Peter Templeman
 
18.
Drinking Buddies (2013)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
Luke and Kate are coworkers at a brewery who spend their nights drinking and flirting heavily. One weekend away together with their significant others proves who really belongs together and who doesn't. (90 mins.)
Director: Joe Swanberg
 
19.
40 Days and 40 Nights (2002)
    1 2 3 4 5 6 7 8 9 10 5.6/10 X  
After a brutal break-up, a young man vows to stay celibate during the forty days of Lent, but finds the girl of his dreams and is unable to do anything about it. (96 mins.)
Director: Michael Lehmann
 
20.
Silver Linings Playbook (2012)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
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. (122 mins.)