Movies Like Win a Date with Brad Benton

If you liked Win a Date with Brad Benton (2005), a movie directed by Casey O'Brian and Peter O'Brian, 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
Don Jon (2013)
★ 6/10
A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.
2
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
3
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
4
The Long Weekend (2005)
★ 5.8/10
Cooper is an actor who sees life as one big party, while Ed is in advertising and takes life too seriously. When Ed gets stressed over a deadline he has to meet, his brother Cooper works hard in trying to get his…
5
That Awkward Moment (2014)
★ 6.1/10
Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The…
6
King Cobra (2016)
★ 5.8/10
It’s 2006, YouTube is in its infancy, and internet porn is still behind a paywall. Taking the stage name Brent Corrigan, a fresh-faced, wannabe adult video performer is molded into a star by Stephen, a closeted gay…
7
The Girl Next Door (2004)
★ 6.8/10
Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds…
8
Your Friends & Neighbors (1998)
★ 5.8/10
Restless and unhappy, two couples get caught up in infidelity and deception. Barry is a sullen businessman married to Mary, a writer who is unsatisfied with their relationship. Mary begins an affair with Jerry, a smug…
9
Preaching to the Perverted (1997)
★ 6.1/10
A computer wizard infiltrates a London sex club to get evidence for a shutdown, but falls for the proprietress.
10
Zack and Miri Make a Porno (2008)
★ 6.3/10
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
11
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…
12
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
13
Barbarosa (1982)
★ 5.9/10
Karl Westover, an inexperienced farm boy, runs away after unintentionally killing a neighbor, whose family pursues him for vengeance. He meets Barbarosa, a gunman of near-mythical proportions, who is himself in danger…
14
Focus (2015)
★ 6.9/10
Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.
15
Hitch (2005)
★ 6.6/10
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques…
16
Anything for Love (2016)
★ 6/10
Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.
17
Barely Legal (2003)
★ 5.9/10
Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to…
18
Hands of Stone (2016)
★ 6.6/10
The legendary Roberto Duran and his equally legendary trainer Ray Arcel change each other's lives.
19
Graphic Desires (2023)
★ 6.8/10
When reclusive Franklin cheats on his partner with a mysterious girl he meets on a dating app, it becomes the start of a deadly obsession.
20
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…