Movies Like Dumping Elaine

If you liked Dumping Elaine (2001), a movie directed by Peter Lydon, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Dating Amber (2020)
★ 7.1/10
Eddie and Amber decide to stage a relationship in order to stop everyone speculating about their sexuality. Eddie is keen to follow his dad into the military, while Amber dreams of moving to the liberal hub of London…
2
Edie (2018)
★ 6.3/10
To try and overcome a lifetime of bitterness and resentment, 83-year-old Edie decides that it is never too late. After packing an old camping bag, she leaves her life behind and embarks on an adventure she never got to…
3
Eddie Izzard: Definite Article (1996)
★ 7.8/10
Eddie arrives on stage through a huge book which opens to reveal herself sitting at the top of a staircase. Then discusses Caesar dog food, 24 hour garages, Latin, and winds her way through James Bond gadgets, Einstein…
4
Mr. Jealousy (1998)
★ 5.9/10
After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia…
5
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
6
Ghost World (2001)
★ 7.1/10
Two quirky, cynical, teenaged girls try to figure out what to do with their lives following high school graduation. After they play a prank on an eccentric, middle-aged record collector, one of them befriends him…
7
Wayne's World (1992)
★ 6.7/10
The adventures of two amiably aimless metal-head friends, Wayne and Garth. From Wayne's basement, the pair broadcast a talk-show called "Wayne's World" on local public access television. The show comes to the attention…
8
Isn't It Romantic (2019)
★ 6.2/10
For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out…
9
Some Kind of Wonderful (1987)
★ 6.8/10
Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and…
10
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
11
Roommates (2026)
★ 6.4/10
When shy college freshman Devon asks cool-girl Celeste to be her roommate, a blossoming friendship quickly spirals into a war of passive aggression.
12
There's Something About Mary (1998)
★ 6.6/10
For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy…
13
The Perfect Date (2019)
★ 6.4/10
No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.
14
Sidelined: The QB and Me (2025)
★ 6.4/10
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving…
15
Let's Make Love (1960)
★ 6.4/10
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
16
American Reunion (2012)
★ 6.4/10
The characters we met a little more than a decade ago return to East Great Falls for their high school reunion. In one long-overdue weekend, they will discover what has changed, who hasn’t, and that time and distance…
17
Mallrats (1995)
★ 6.8/10
Both dumped by their girlfriends, two best friends seek refuge in the local mall. Eventually, they decide to try and win back their significant others and take care of their respective nemeses.
18
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
19
About Last Night (2014)
★ 6/10
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to…
20
St. Elmo's Fire (1985)
★ 6.1/10
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick…