Movies Like Maybe If You...

If you liked Maybe If You... (2005), a comedy movie directed by Michael McCudden, here are 19 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
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.
2
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
3
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.
4
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.
5
Room Service (1938)
★ 6.5/10Also comedy
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
6
Wet Hot American Summer (2001)
★ 6.2/10Also comedy
It's the last day of Camp Firewood's season, but there's still time for the big talent show, a little romance… and for everyone to be wiped out by the piece of NASA's Skylab that's hurtling toward Earth.
7
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
8
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.
9
Fist Fight (2017)
★ 6/10Also comedy
When one school teacher gets the other fired, he is challenged to an after-school fight.
10
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!
11
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.
12
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
13
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
14
Pitch Perfect 3 (2017)
★ 6.5/10Also comedy
After the highs of winning the world championships, the Bellas find themselves split apart and discovering there aren't job prospects for making music with your mouth. But when they get the chance to reunite for an…
15
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.
16
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
17
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
18
Don't Tell Mom the Babysitter's Dead (1991)
★ 6.2/10Also comedy
Sue Ellen Crandell is a teenager eagerly awaiting her mother's summer-long absence. While the babysitter looks after her rambunctious younger siblings, Sue Ellen can party and have fun. But then the babysitter abruptly…
19
American Reunion (2012)
★ 6.4/10Also comedy
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…