500 Days of Summer
1 / 15VIEW ALL
Zooey Deschanel stars as Summer, a woman who doesn't believe in true love, and Joseph Gordon-Levitt plays Tom, a hopeless romantic who falls hard for her in the quirky 2009 romantic dramedy 500 Days of Summer.
The First Wives Club
2 / 15VIEW ALL
Empowering and funny, the popular 1996 chick flick The First Wives Club stars Goldie Hawn, Diane Keaton and Bette Midler as three women who team up for revenge when their husbands each leave them for younger women.
About a Boy
3 / 15VIEW ALL
In some of these movies the characters aren't mature enough for a relationship, like Will (Hugh Grant) in 2002's About a Boy. But with the help of his new little friend Marcus (Nicholas Hoult), Will might grow up.
4 / 15VIEW ALL
Alfred Hitchcock's 1964 sexual thriller Marnie stars Tippi Hedren as a pathological thief who's afraid of intimacy due to a childhood trauma. Her boss, Mark (Sean Connery), tries to cure Marnie by blackmailing her into marrying him.
5 / 15VIEW ALL
The classic 1966 dramedy Alfie starring Michael Caine as a carefree womanizing London bachelor who is suddenly faced with the consequences of his actions, was remade in 2004 with Jude Law in the lead.
6 / 15VIEW ALL
The sheltered Judy Benjamin has always been dependent on men, so joining the army after her new husband dies is a huge adjustment, but she comes to cherish her independence in this popular 1980 comedy starring Goldie Hawn.
7 / 15VIEW ALL
Love is a business for professional date doctor Hitch (Will Smith) who's happily single. But when he meets beautiful journalist Sara (Eva Mendes), also avoiding commitment, their mutual cynicism starts to waver in this 2005 comedy.
8 / 15VIEW ALL
Children's author Beatrix Potter (Renee Zellweger) chooses fictional bunnies and spinsterhood in Victorian England over marrying a man she doesn't love in the 2006 biopic Miss Potter. But true love might come when she least expects it.
The Other Woman
9 / 15VIEW ALL
The single life looks good after seeing 2014 dramedy The Other Woman starring Nikolaj Coster-Waldau as a philanderer whose wife (Leslie Mann) and mistresses (Cameron Diaz and Kate Upton) join forces to make him pay for his lying and cheating.
10 / 15VIEW ALL
In the 1998 biopic Elizabeth, The Virgin Queen (Cate Blanchett) had a good time being single, and refused to wed despite pressure to produce an heir. Elizabeth's cynicism about marriage was understandable, considering her father was Henry VIII—who was known for his many marriages and affairs.
Frankie & Johnny
11 / 15VIEW ALL
Al Pacino and Michelle Pfeiffer reteamed for this sensitive 1991 Garry Marshall drama, centering on a fry cook, newly released from prison, who's determined to win over a waitress, reluctant to get involved because of a painful secret.
12 / 15VIEW ALL
Many movies have been based on Jane Austen's romantic novels set in upper class 19th century England, but the 2007 biopic Becoming Jane, starring Anne Hathaway, shows Austen choosing to remain single after losing the love of her life.
He's Just Not That Into You
13 / 15VIEW ALL
The 2009 romantic dramedy He's Just Not That Into You explores the art of reading human behavior, through interconnecting stories. The star-studded cast is particularly impressive, featuring: Jennifer Aniston, Bradley Cooper, Scarlett Johansson, Drew Barrymore and Ben Affleck.
14 / 15VIEW ALL
The Holiday stars Cameron Diaz and Kate Winslet as two vacationing women who look forward to being single following disappointments in love. But after swapping homes in different countries, love finds each of them again, when it's least welcome.
James Bond Franchise
15 / 15VIEW ALL
Bachelorhood would be hard to give up for a man with as many sexy, gorgeous women swarming around him as James Bond. Besides, when he does fall in love, she usually gets killed off, like Vesper in Casino Royale.