Movies Like It's A 40-Something Men Thing!

If you liked It's A 40-Something Men Thing! (2023), a movie, 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
Mrs. Winterbourne (1996)
★ 7.3/10
Connie Doyle is eighteen, pregnant and alone. She accidentally ends up on a train where she meets Hugh Winterbourne and his wife pregnant Patricia. The train wrecks and she wakes up in the hospital to find out that…
2
My Awkward Sexual Adventure (2012)
★ 6.7/10
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
3
To Wong Foo, Thanks for Everything! Julie Newmar (1995)
★ 7.5/10
Veteran drag queens Vida Boheme and Noxeema Jackson take novice Chi-Chi Rodriguez under their wing on a madcap road trip across the country to compete in the Drag Queen of America pageant in Los Angeles.
4
Pee-wee's Big Adventure (1985)
★ 6.5/10
The eccentric and childish Pee-wee Herman embarks on a big adventure when his beloved bicycle is stolen. Armed with information from a fortune-teller and a relentless obsession with his prized possession, Pee-wee…
5
Cover Girl (1944)
★ 6.4/10
A nightclub dancer makes it big in modeling, leaving her dancer boyfriend behind.
6
Weird Science (1985)
★ 6.5/10
Two unpopular teenagers, Gary and Wyatt, fail at all attempts to be accepted by their peers. Their desperation to be liked leads them to "create" a woman via their computer. Their living and breathing creation is a…
7
I Can't Think Straight (2008)
★ 7.5/10
Tala, a London-based Palestinian, is preparing for her elaborate Middle Eastern wedding when she meets Leyla, a young British Indian woman who is dating her best friend. Spirited Christian Tala and shy Muslim Leyla…
8
¿Quieres ser mi hijo? (2023)
★ 8.4/10
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
9
Wonder Wheel (2017)
★ 6.4/10
The story of four characters whose lives intertwine amid the hustle and bustle of the Coney Island amusement park in the 1950s: Ginny, an emotionally volatile former actress now working as a waitress in a clam house…
10
Girls Trip (2017)
★ 6.8/10
Four girlfriends take a trip to New Orleans for an annual festival and, along the way, rediscover their wild sides and strengthen the bonds of sisterhood.
11
Nine 1/2 Weeks (1986)
★ 6.1/10
An erotic story about a woman, the assistant of an art gallery, who gets involved in an impersonal affair with a man. She barely knows about his life, only about the sex games they play, so the relationship begins to…
12
Cadillac Records (2008)
★ 7.1/10
The story of sex, violence, race and rock and roll in 1950s Chicago, and the exciting but turbulent lives of some of America's musical legends, including Muddy Waters, Leonard Chess, Little Walter, Howlin' Wolf, Etta…
13
A Good Old Fashioned Orgy (2011)
★ 5.8/10
A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.
14
Chasing Amy (1997)
★ 6.7/10
Holden and Banky are comic book artists. Everything is going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.
15
Bloomington (2010)
★ 6.5/10
A former child actress attends college in search of independence and ends up becoming romantically involved with a female professor. Their relationship thrives until an opportunity to return to acting forces her to…
16
Ferdinand (2017)
★ 7.2/10
Ferdinand, a little bull, prefers sitting quietly under a cork tree just smelling the flowers versus jumping around, snorting, and butting heads with other bulls. As Ferdinand grows big and strong, his temperament…
17
Fanboys (2009)
★ 6.2/10
In 1999, Star Wars fanatics take a cross-country trip to George Lucas' Skywalker Ranch so their dying friend can see a screening of The Phantom Menace before its release.
18
Entergalactic (2022)
★ 7.7/10
Ambitious artist Jabari attempts to balance success and love when he moves into his dream Manhattan apartment and falls for his next-door neighbor.
19
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…
20
Fifty Shades Darker (2017)
★ 6.5/10
When a wounded Christian Grey tries to entice a cautious Ana Steele back into his life, she demands a new arrangement before she will give him another chance. As the two begin to build trust and find stability, shadowy…