Entertainment
30+ Great Movies About Dating in Your 20s
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
- Cal Weaver (Steve Carell) is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily (Julianne Moore). Cal's seemingly perfect life unravels, ...more
- Best pals Jason (Zac Efron) and Daniel (Miles Teller) indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey (Michael B. ...more
- Jamie (Mila Kunis) is a New York-based executive recruiter who entices Dylan (Justin Timberlake), an art director from Los Angeles, to take a job at the New York office of GQ magazine. Finding that ...more
- Lifelong friends Emma (Natalie Portman) and Adam (Ashton Kutcher) take their relationship to the next level by having sex. Afraid of ruining their friendship, the new lovers make a pact to keep ...more
- Struggling musician Peter Bretter (Jason Segel) is better-known as the boyfriend of TV star Sarah Marshall (Kristen Bell). After she unceremoniously dumps him, he feels lost and alone but makes a ...more
- Tom (Joseph Gordon-Levitt), greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer (Zooey Deschanel), suddenly dumps him. He reflects on their 500 days ...more
- On his way to Vienna, American Jesse (Ethan Hawke) meets Celine (Julie Delpy), a student returning to Paris. After long conversations forge a surprising connection between them, Jesse convinces ...more
- A group of recent college graduates embark on a series of misadventures in the real world. There's Kirby (Emilio Estevez), a waiter who wants to be a lawyer; Kevin (Andrew McCarthy), a moody writer ...more
- Rob Gordon (John Cusack) is the owner of a failing record store in Chicago, where he sells music the old-fashioned way -- on vinyl. Although they have an encyclopedic knowledge of pop music and are ...more
- Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into ...more
- High school student Chris Brander (Ryan Reynolds) loves his best friend, Jamie Palamino (Amy Smart). He finally confesses his feelings, but she tells him that she just wants to be friends, and he ...more
- On a magical night when they are in in their 20s, Jonathan (John Cusack) meets Sara (Kate Beckinsale). He finds it love at first sight, but Sara believes in destiny. After 10 years the two -- with ...more
- As bass guitarist for a garage-rock band, Scott Pilgrim (Michael Cera) has never had trouble getting a girlfriend; usually, the problem is getting rid of them. But when Ramona Flowers (Mary Elizabeth ...more
- 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
- After many years away, television bit part actor Andrew Largeman (Zach Braff) returns to his small home town in New Jersey to attend his mother's funeral. There he is confronted by various aspects of ...more
- In 1977, college graduates Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a contentious car ride from Chicago to New York, during which they argue about whether men and women can ...more
- Recent college graduate Ryden Malby (Alexis Bledel) has a grand plan: Find a fabulous apartment and land a job at a prestigious publishing house. However, her rival Jessica steals her dream job, and ...more
- 18A vacuum repairman (Glen Hansard) moonlights as a street musician and hopes for his big break. One day a Czech immigrant (Marketa Irglova), who earns a living selling flowers, approaches him with the ...more
- 19On July 15, 1988 -- the day of their college graduation -- two people from opposite sides of the tracks begin a lifelong friendship. Emma (Anne Hathaway), an idealist from a working-class family, ...more
- After college, Lelaina (Winona Ryder) films a documentary about herself and friends as they flounder in their attempts to forge relationships and begin careers. Vickie (Janeane Garofalo) works ...more
- An immature, newly unemployed comic (Jenny Slate) must navigate the murky waters of adulthood after her fling with a graduate student (Jake Lacy) results in an unplanned pregnancy.
- 22In Seattle during the era of grunge music, the lives and relationships of a group of young people, all living in the same apartment building, go through a period of flux. Among them are waitress and ...more
- Comedian Alvy Singer (Woody Allen) examines the rise and fall of his relationship with struggling nightclub singer Annie Hall (Diane Keaton). Speaking directly to the audience in front of a bare ...more
- Frances (Greta Gerwig) goes from apartment to apartment in Brooklyn as she looks for a job and a stable partner.
- In this adaptation of David Mamet's hit 1974 off-Broadway play "Sexual Perversity in Chicago," Danny (Rob Lowe) and Bernie (James Belushi) are a couple of single guys who live in the Windy City and ...more
