Movies Like My Girlfriend's Boyfriend

If you liked My Girlfriend's Boyfriend (1999), a comedy movie directed by Kenneth Schapiro, 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
Bachelor Party (1984)
★ 6.3/10Also comedy
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.
2
The Wedding Ringer (2015)
★ 6.5/10Also comedy
Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO…
3
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
4
The People We Hate at the Wedding (2022)
★ 6.3/10Also comedy
A dysfunctional family that can't seem to get along and get it together reluctantly reunites for a family wedding. As their many skeletons are wrenched from the closet, it turns out to be just what this singular family…
5
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…
6
The Importance of Being Earnest (1952)
★ 7.2/10Also comedy
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
7
72 HOURS (2026)
★ 6.8/10Also comedy
To save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.
8
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
9
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
10
Walk Hard: The Dewey Cox Story (2007)
★ 6.6/10Also comedy
Following a childhood tragedy, Dewey Cox follows a long and winding road to music stardom. Dewey perseveres through changing musical styles, an addiction to nearly every drug known and bouts of uncontrollable rage.
11
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
12
The Ritz (1976)
★ 6/10Also comedy
To escape from a mobster, businessman Gaetano Proclo orders a cab driver to take him to a place where he can't be found. Unfortunately for Gaetano, the place turns out to be a gay bathhouse.
13
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
14
A Wedding (1978)
★ 6.3/10Also comedy
Muffin's wedding to Dino Corelli is to be a big affair. Except the ageing priest isn't too sure of the ceremony, only the families actually turn up as the Corelli Italian connection is suspect, security guards watch…
15
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
16
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
17
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
18
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
19
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
20
The Thing About Harry (2020)
★ 6.8/10Also comedy
Two high school enemies, uber-jock Harry and out-and-proud Sam, are forced to share a car ride to their Missouri hometown for a friend's engagement party on Valentine's Day. Things take a turn when Sam learns Harry has…