Dating in your 20s combines all the drama of young love with the added stress of a ticking biological clock. Luckily, that combination makes for some great entertainment. The top dating in your 20s movies are some of the best romantic comedies of all time. This is a list of the top movies about twentysomethings dating, featuring everything from When Harry Met Sally... to Obvious Child to Garden State.
What movies will you find on this list of the best movies for 20 somethings? Maybe you'll vote Reality Bites to the top. A group of recent college graduates struggle through new careers and messy relationships in this 1994 film directed by Ben Stiller. Before Sunrise – also starring a young Ethan Hawke – is another great movie about a relationship between twentysomethings. Many romantic movies follow the female perspective, but Swingers is a great film about guys in their 20s looking for love. Other good films featured on this roundup of movies about dating in your 20s include Francis Ha, About Last Night, and Singles.
Do you have a favorite dating movie? Give the best films a thumbs up and add any great flicks that are missing.
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5112Crazy, Stupid, Love.
Emma Stone, Julianne MooreReleased: 2011
Directed by: John Requa, Glenn Ficarra
Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra... more on Wikipedia2
4215(500) Days of Summer
Zooey Deschanel, Minka KellyReleased: 2009
Directed by: Marc Webb
(500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc... more on Wikipedia3
348Reality Bites
Winona Ryder, Renée ZellwegerReleased: 1994
Directed by: Ben Stiller
Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by... more on Wikipedia4
3614Friends with Benefits
Emma Stone, Mila KunisReleased: 2011
Directed by: Will Gluck
Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and... more on Wikipedia5
319That Awkward Moment
Zac Efron, Miles TellerReleased: 2014
Directed by: Tom Gormican
That Awkward Moment is a 2014 American romantic comedy-drama film directed by Tom Gormican.... more on Wikipedia6
289Forgetting Sarah Marshall
Mila Kunis, Kristen BellReleased: 2008
Directed by: Nicholas Stoller
Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas... more on Wikipedia7
2410When Harry Met Sally...
Meg Ryan, Billy CrystalReleased: 1989
Directed by: Rob Reiner
When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and... more on Wikipedia8
218Swingers
Heather Graham, Vince VaughnReleased: 1996
Directed by: Doug Liman
This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on... more on Wikipedia9
229Just Friends
Ryan Reynolds, Anna FarisReleased: 2005
Directed by: Roger Kumble
Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble,... more on Wikipedia10
2210Something Borrowed
Kate Hudson, Ginnifer GoodwinReleased: 2011
Directed by: Luke Greenfield
Something Borrowed is a 2011 American romantic comedy film based on Emily Giffin's book of the... more on Wikipedia11
2413No Strings Attached
Natalie Portman, Ashton KutcherReleased: 2011
Directed by: Ivan Reitman
No Strings Attached is a 2011 American romantic comedy film directed by Ivan Reitman and... more on Wikipedia12
2010Scott Pilgrim vs. the World
Anna Kendrick, Chris EvansReleased: 2010
Directed by: Edgar Wright
Scott Pilgrim vs. the World is a 2010 comedy film co-written, produced and directed by Edgar... more on Wikipedia13
2111Annie Hall
Woody Allen, Diane KeatonReleased: 1977
Directed by: Woody Allen
Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York... more on Wikipedia14
1910Waitress
Keri Russell, Nathan FillionReleased: 2007
Directed by: Adrienne Shelly
Waitress is a 2007 American comedy-drama film written and directed by Adrienne Shelly, who... more on Wikipedia15
155St. Elmo's Fire
Demi Moore, Rob LoweReleased: 1985
Directed by: Joel Schumacher
St. Elmo's Fire is a 1985 American coming-of-age film directed by Joel Schumacher. The film,... more on Wikipedia16
158High Fidelity
Catherine Zeta-Jones, Bruce SpringsteenReleased: 2000
Directed by: Stephen Frears
High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring... more on Wikipedia17
1710Serendipity
Kate Beckinsale, John CusackReleased: 2001
Directed by: Peter Chelsom
Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale.... more on Wikipedia18
2625Before Sunrise
Ethan Hawke, Julie DelpyReleased: 1995
Directed by: Richard Linklater
Before Sunrise is a 1995 American romantic drama film directed by Richard Linklater and... more on Wikipedia19
1713One Day
Anne Hathaway, Patricia ClarksonReleased: 2011
Directed by: Lone Scherfig
One Day is a 2011 romance drama film directed by Lone Scherfig. It was adapted by David... more on Wikipedia20
1313Ruby Sparks
Annette Bening, Deborah Ann WollReleased: 2012
Directed by: Valerie Faris, Jonathan Dayton
Ruby Sparks is a 2012 romantic comedy-drama film directed by Jonathan Dayton and Valerie... more on Wikipedia21
1415Singles
Paul Giamatti, Eddie VedderReleased: 1992
Directed by: Cameron Crowe
Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron... more on Wikipedia22
68In a Relationship
Emma Roberts, Michael AngaranoReleased: 2018
Directed by: Sam Boyd
In a Relationship is an 2018 American comedy drama film directed by Sam Boyd. As long-term... more on Wikipedia23
1018Once
Glen Hansard, Markéta IrglováReleased: 2006
Directed by: John Carney
Once is a 2007 Irish musical film written and directed by John Carney. Set in Dublin, Ireland,... more on Wikipedia24
815Post Grad
Alexis Bledel, Michael KeatonReleased: 2009
Directed by: Vicky Jenson
Post Grad is a 2009 romantic comedy film directed by Vicky Jenson and starring Alexis Bledel,... more on Wikipedia25
613Lola Versus
Debra Winger, Bill PullmanReleased: 2012
Directed by: Daryl Wein
Lola Versus is a 2012 American romantic comedy film directed by Daryl Wein. The screenplay was... more on Wikipedia