Movies Like Well, This Is Awkward

If you liked Well, This Is Awkward (2022), 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
The Client List (2010)
★ 5.9/10
After she and her husband lose their jobs, a former Texas homecoming queen inadvertently finds herself in the middle of a prostitution ring after she unknowingly accepts a position at a massage parlor.
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
The Threesome (2025)
★ 6.3/10
Connor has a threesome with his long-time crush Olivia and an alluring stranger named Jenny. It surprisingly serves as the spark to a full blown relationship with Olivia, until both women end up pregnant and all three…
4
The Overnight (2015)
★ 5.9/10
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.
5
Magic Mike (2012)
★ 6.2/10
Mike, an experienced stripper, takes a younger performer called The Kid under his wing and schools him in the arts of partying, picking up women, and making easy money.
6
Eating Out 2: Sloppy Seconds (2006)
★ 6.1/10
How far would you go to get the person of your dreams? With the help of Gwen and Tiffani, Kyle pretends to be heterosexual in order to land Troy, the new guy (and nude model) who's turning the heads of both men and…
7
Splendor (1999)
★ 6.2/10
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
8
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…
9
Kissing Is the Easy Part (2026)
★ 7.3/10
Sean's gunning for MIT. Flora's ditching the SAT. A secret deal with her tenured parents sparks a romance that challenges everything they believe in.
10
Secretary (2002)
★ 6.8/10
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
11
American Wedding (2003)
★ 6.2/10
With high school a distant memory, Jim and Michelle are getting married — and in a hurry, since Jim's grandmother is sick and wants to see him walk down the aisle — prompting Stifler to throw the ultimate bachelor…
12
The Rules of Attraction (2002)
★ 6.2/10
The incredibly spoiled and overprivileged students of Camden College are a backdrop for an unusual love triangle between a drug dealer, a virgin and a bisexual classmate.
13
American Pie 2 (2001)
★ 6.4/10
After a year apart - attending different schools, meeting different people - the guys rent a beach house and vow to make this the best summer ever. As it turns out, whether that will happen or not has a lot to do with…
14
Bob & Carol & Ted & Alice (1969)
★ 6.3/10
After returning to Los Angeles from a group therapy session, documentary filmmaker Bob Sanders and his wife, Carol, find themselves becoming vigilante couples counselors, offering unsolicited advice to their best…
15
Threesome (1994)
★ 6.4/10
At a sizable public college, high-minded student Eddy is forced to room with the slovenly Stuart, but the pair strike up a surprising friendship. When attractive co-ed Alex is assigned to live with the two male…
16
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…
17
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
18
Deep End (1971)
★ 7/10
London, England. Mike, a fifteen-year-old boy, gets a job in a bathhouse, where he meets Susan, an attractive young woman who works there as an attendant.
19
The 40 Year-Old Virgin (2005)
★ 6.4/10
Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers…
20
Merrily We Live (1938)
★ 7/10
Society matron Emily Kilbourne has a habit of hiring ex-cons and hobos as servants. Her latest find is a handsome tramp who shows up at her doorstep and ends up in a chauffeur's uniform. He also catches the eye of…