Entertainment 30+ Great Movies About Dating in Your 20s  

Ranker Film
426 votes 82 voters 7.3k views 35 items

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.

list ordered by

1
10 0
Just Friends is listed (or ranked) 1 on the list 30+ Great Movies About Dating in Your 20s
Ryan Reynolds, Anna Faris, Amy Smart
Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble, and starring Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein and Christopher Maquette. The plot ...more

2
25 4
Crazy, Stupid, Love. is listed (or ranked) 2 on the list 30+ Great Movies About Dating in Your 20s
Emma Stone, Julianne Moore, Ryan Gosling
Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra and John Requa, and written by Dan Fogelman. It stars Steve Carell, Ryan Gosling, Julianne Moore, Emma ...more

3
17 4
Something Borrowed is listed (or ranked) 3 on the list 30+ Great Movies About Dating in Your 20s
Kate Hudson, Ginnifer Goodwin, Peyton List
Something Borrowed is a 2011 American romantic comedy film based on Emily Giffin's book of the same name, directed by Luke Greenfield, starring Ginnifer Goodwin, Kate Hudson, Colin Egglesfield, ...more

4
14 5
Forgetting Sarah Marshall is listed (or ranked) 4 on the list 30+ Great Movies About Dating in Your 20s
Mila Kunis, Kristen Bell, Russell Brand
Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more

5
14 5
When Harry Met Sally... is listed (or ranked) 5 on the list 30+ Great Movies About Dating in Your 20s
Meg Ryan, Billy Crystal, Carrie Fisher
When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the ...more

6
13 5
Friends with Benefits is listed (or ranked) 6 on the list 30+ Great Movies About Dating in Your 20s
Emma Stone, Mila Kunis, Justin Timberlake
Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and starring Justin Timberlake and Mila Kunis. The film features a supporting cast that includes Patricia ...more

7
8 1
St. Elmo's Fire is listed (or ranked) 7 on the list 30+ Great Movies About Dating in Your 20s
Demi Moore, Rob Lowe, Judd Nelson
St. Elmo's Fire is a 1985 American coming-of-age film directed by Joel Schumacher. The film, starring Emilio Estevez, Rob Lowe, Andrew McCarthy, Demi Moore, Judd Nelson, Ally Sheedy, and Mare ...more

8
11 4
No Strings Attached is listed (or ranked) 8 on the list 30+ Great Movies About Dating in Your 20s
Natalie Portman, Ashton Kutcher, Kevin Kline
A guy and girl try to keep their relationship strictly physical, but it's not long before they learn that they want something more.

9
15 8
(500) Days of Summer is listed (or ranked) 9 on the list 30+ Great Movies About Dating in Your 20s
Zooey Deschanel, Minka Kelly, Chloë Grace Moretz
(500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc Webb. On January 8, Tom Hansen (Joseph Gordon-Levitt) meets Summer Finn (Zooey Deschanel), his ...more

10
11 5
That Awkward Moment is listed (or ranked) 10 on the list 30+ Great Movies About Dating in Your 20s
Zac Efron, Miles Teller, Michael B. Jordan
That Awkward Moment is a 2014 American romantic comedy-drama film directed by Tom Gormican. Three best friends find themselves where we've all been - at that confusing moment in every dating ...more

11
11 5
Serendipity is listed (or ranked) 11 on the list 30+ Great Movies About Dating in Your 20s
Kate Beckinsale, John Cusack, Bridget Moynahan
Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale. It was written by Marc Klein and directed by Peter Chelsom. The music score is composed by Alan ...more

12
10 5
Reality Bites is listed (or ranked) 12 on the list 30+ Great Movies About Dating in Your 20s
Winona Ryder, Renée Zellweger, Ben Stiller
Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by Ben Stiller. It stars Winona Ryder, Ethan Hawke and Stiller, with supporting roles by Janeane ...more

13
10 6
Scott Pilgrim vs. the World is listed (or ranked) 13 on the list 30+ Great Movies About Dating in Your 20s
Anna Kendrick, Chris Evans, Mary Elizabeth Winstead
Scott Pilgrim vs. the World is a 2010 comedy film co-written, produced and directed by Edgar Wright, based on the graphic novel series Scott Pilgrim by Bryan Lee O'Malley. It stars Michael Cera ...more

14
12 9
Before Sunrise is listed (or ranked) 14 on the list 30+ Great Movies About Dating in Your 20s
Ethan Hawke, Julie Delpy, Adam Goldberg
Before Sunrise is a 1995 American romantic drama film directed by Richard Linklater and written by Linklater and Kim Krizan. The film follows Jesse, a young American man, and Céline, a ...more

15
9 6
One Day is listed (or ranked) 15 on the list 30+ Great Movies About Dating in Your 20s
Anne Hathaway, Patricia Clarkson, Jim Sturgess
One Day is a 2011 romance drama film directed by Lone Scherfig. It was adapted by David Nicholls from his 2009 novel of the same name. It stars Anne Hathaway and Jim Sturgess. Focus Features ...more

16
7 5
Swingers is listed (or ranked) 16 on the list 30+ Great Movies About Dating in Your 20s
Heather Graham, Vince Vaughn, Jon Favreau filmography
This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on the 'eastside' of Hollywood, California during the 1990s swing revival. Written by Jon Favreau and ...more

17
6 4
High Fidelity is listed (or ranked) 17 on the list 30+ Great Movies About Dating in Your 20s
Catherine Zeta-Jones, Bruce Springsteen, Jack Black
High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring John Cusack and Iben Hjejle. The film is based on the 1995 British novel of the same name by Nick ...more

18
4 2
Waitress is listed (or ranked) 18 on the list 30+ Great Movies About Dating in Your 20s
Keri Russell, Nathan Fillion, Andy Griffith
Waitress is a 2007 American comedy-drama film written and directed by Adrienne Shelly, who also appears in a supporting role. The film debuted at the 2007 Sundance Film Festival and went into ...more

19
6 5
Once is listed (or ranked) 19 on the list 30+ Great Movies About Dating in Your 20s
Glen Hansard, Markéta Irglová, Darren Healy
Once is a 2007 Irish musical film written and directed by John Carney. Set in Dublin, Ireland, the naturalistic drama stars musicians Glen Hansard and Markéta Irglová. ...more

20
5 4
Frances Ha is listed (or ranked) 20 on the list 30+ Great Movies About Dating in Your 20s
Greta Gerwig, Adam Driver, Michael Zegen
Frances Ha is a 2013 American comedy-drama film directed by Noah Baumbach and written by Baumbach and Greta Gerwig. Gerwig also plays the title role. The film premiered at the Telluride Film ...more

21
2 1
In a Relationship is listed (or ranked) 21 on the list 30+ Great Movies About Dating in Your 20s
Emma Roberts, Michael Angarano, Dree Hemingway
In a Relationship is an 2018 American comedy drama film directed by Sam Boyd. As long-term couple Haillie (Emma Roberts) and Owen (Michael Angarano) struggle with staying together, their friends ...more

22
7 7
Obvious Child is listed (or ranked) 22 on the list 30+ Great Movies About Dating in Your 20s
Jenny Slate, Jake Lacy, Gaby Hoffmann
Obvious Child is a 2014 American romantic comedy-drama film directed by Gillian Robespierre. After a drunken one-night stand, stand-up comedian Donna (Jenny Slate) finds out she is pregnant and ...more

23
6 6
Annie Hall is listed (or ranked) 23 on the list 30+ Great Movies About Dating in Your 20s
Woody Allen, Sigourney Weaver, Christopher Walken
Annie Hall is a 1977 American romantic comedy directed by Woody Allen from a screenplay he co-wrote with Marshall Brickman. Produced by Allen's manager, Charles H. Joffe, the film stars Allen as ...more

24
5 5
Singles is listed (or ranked) 24 on the list 30+ Great Movies About Dating in Your 20s
Paul Giamatti, Eddie Vedder, Chris Cornell
Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron Crowe. The film stars Bridget Fonda, Campbell Scott, Kyra Sedgwick, and Matt Dillon.

25
3 3
Post Grad is listed (or ranked) 25 on the list 30+ Great Movies About Dating in Your 20s
Alexis Bledel, Michael Keaton, Jane Lynch
Post Grad is a 2009 romantic comedy film directed by Vicky Jenson and starring Alexis Bledel, about a recent college graduate who moves back in with her family while she figures out what she ...more