Highest-Rated Movies about 'Sexual Awkwardness'

The 40 Year Old Virgin (2005), American Pie (1999), Everything You Always Wanted to Know About Sex * But Were Afraid to Ask (1972), The Inbetweeners Movie (2011), American Reunion (2012), Sex Drive (2008), Road Trip (2000), My Awkward Sexual Adventure (2012) ... Let's take a look at the ranked list of the best Sexual Awkwardness movies.

#1. The 40 Year Old Virgin (2005)

Storyline: Andy at the age of 40 still hasn't had sex. He lets his secret slip at a poker game with his buds from work. After the revealing all his friends are on a mission to help get him laid. Along the way Andy meets a nice mom, Trish, and they fall head over heels for each other.

Plot Keywords: comedy, romance, adult, coming of age, humor, sex, friendship ...

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#2. American Pie (1999)

Storyline: Jim, Oz, Finch and Kevin are four friends who make a pact that before they graduate they will all lose their virginity. The hard job now is how to reach that goal by prom night. Whilst Oz begins singing to grab attention and Kevin tries to persuade his girlfriend, Finch tries any easy route of spreading rumors and Jim fails miserably. Whether it is being caught on top of a pie or on the Internet, Jim always ends up with his trusty sex advice from his father. Will they achieve their goal of getting laid by prom night? Or will they learn something much different?

Plot Keywords: teen, comedy, sex, coming of age, american, high school, friendship ...

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#3. Everything You Always Wanted to Know About Sex * But Were Afraid to Ask (1972)

Storyline: Seven segments related to one another only in that they all purport to be based on sections of the book by David Reuben. The segments range from "Do Aphrodisiacs Work?" in which a court jester gives an aphrodisiac to the Queen and is, in the end, beheaded to "What Happens During Ejaculation?" in which we watch "control central" during a successful seduction.

Plot Keywords: comedy, sex education, satire, sexual humor, 1970s, american film, anthology ...

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#4. The Inbetweeners Movie (2011)

Storyline: Best friends Will McKenzie, Simon Cooper, Jay Cartwright and Neil Sutherland - who are not among the social outcasts, but also not cool enough to hang out with the cool kids who they aspire to be - have just graduated from their suburban London high school. Simon has finally been able to get Carli D'Amato, who he has been in love with since they were children, to be his girlfriend. Largely because they will be going away to different schools in the fall, Carli breaks up with him. To get Simon's singularly focused mind off Carli, his three best mates decide to take him on vacation for two weeks to get some sun, sand and girls before they move onto the next chapter of their lives in the fall. Neil makes the decision for them to go to Malia on the isle of Crete, a popular summer tourist destination for many a Brit. Jay, with inheritance money in hand, believes he can have the pick of any girl he wants. Neil has to decide what constitutes not cheating on his girlfriend, Nicole. Will wants...

Plot Keywords: comedy, teen, british film, coming of age, friendship, adventure, holiday ...

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#5. American Reunion (2012)

Storyline: Over a decade has passed and the gang return to East Great Falls, Michigan, for the weekend. They will discover how their lives have developed as they gather for their high school reunion. How has life treated Michelle, Jim, Heather, Oz, Kevin, Vicky, Finch, Stifler, and Stifler's mom? In the summer of 1999, it was four boys on a quest to lose their virginity. Now Kara is a cute high school senior looking for the perfect guy to lose her virginity to.

Plot Keywords: comedy, teen, nostalgia, sexual humor, coming of age, friendship, adult content ...

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#6. Sex Drive (2008)

Storyline: Ian is a high school senior in suburban Chicago, plagued by being a virgin. Online he's inflated his resume, met Ms. Tasty, and agreed to drive to Knoxville where she promises sex. He steals his homophobic, macho brother's GTO, and, with his two best friends, Lance and Felicia, heads south. Every young woman who meets Lance, including Felicia, is attracted to him, as he practices his aptly learned "Pick-Up Artist" skills. Ian, on the other hand, is a decent guy who wouldn't mind if his friendship with Felicia became a romance. By the time they get to Knoxville, they have encountered a jealous boyfriend, a menacing hitchhiker, jail birds, carjackers, an Amish community, and Ian's better judgment.

Plot Keywords: road movie, sexual humor, coming of age, bromance, sexual exploration, sexual awakening, crude humor ...

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#7. Road Trip (2000)

Storyline: Josh and Tiffany have been together since they were kids. ENTER Beth, a sexy blonde going to college with Josh. One night, Josh and Beth hook up and make a videotape the same day that Josh plans to mail a video to Tiffany of him talking about college life. The wrong tape gets sent, forcing Josh, along with a few pals, to go to Austin, where Tiffany is, and stop her from seeing the tape. Full of laughs, you'll be sure to enjoy Road Trip.

Plot Keywords: comedy, youth, road movie, adventure, sexual humor, college, friendship ...

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#8. My Awkward Sexual Adventure (2012)

Storyline: Thirty-seven year old Winnipeg-based accountant Jordan Abrams, a proverbial doormat of a man, has pined after Rachel Stern since he was twelve. He finally got her to be his girlfriend last year after she being a peripheral or not so peripheral part of his life all these years. Now, in a relationship for a year, Jordan plans on asking her to marry him on a week-long romantic vacation they are taking to Niagara Falls. Rachel not only decides not to go on the trip, but dumps him when he, learning that she isn't going, asks her to marry him the day before the trip instead. The primary reason she dumps him?: he's lousy in bed, she not being able to envision bad, boring sex with him for the rest of her life. Rachel convinces him to take the vacation by himself, instead hanging out in Toronto with his college friend Dandak, his return from the vacation when they will talk about the break-up in more detail. Dandak, a sex machine, sees his role in his mending his friend's broken heart as getting him back in the dating scene. Jordan, however, can only think about getting Rachel back, he believing the best way to be a better lover by getting sex pointers from Dandak and to make Rachel jealous by texting her a photograph of him together with a sexy woman. The woman who obliges his sexy photograph request is Julia Bowe, a stripper he befriends. Due to Dandak's changing circumstance, Jordan turns to sexually-liberated Jules also to be his non-sex sex teacher, he in return helping her manage her dismal finances, she who has no concept of money or its management beyond buying whatever she wants. In Jordan and Jules' not always smooth student-teacher and teacher-student relationships, in what ends up being Jordan and Rachel's truncated week apart, and in Dandak dealing with his new situation, each in the collective may eventually come to the realization of what and who he or she wants in life, the further issue being if they can admit these realizations to themselves and the people that matter.—Huggo

Plot Keywords: comedy, romance, sex comedy, coming of age, awkward, adventure, romantic ...

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#9. The To Do List (2013)

Storyline: Brandy Klark (Aubrey Plaza) has just graduated from high school where she excelled in every subject, except real-life sexual education. When her older sister tells her how important it is to be experienced, Brandy writes out a sex to do list for herself for the summer. Her friend Cameron might be the perfect guinea pig while she sets her sights on the popular and sexy Rusty Waters as the ultimate end goal. But once feelings get in the way, it becomes much harder for Brandy to check off the remaining items on her sex to do list.

Plot Keywords: sex education, coming of age, female protagonist, high school life, sexual exploration, humor, friendship ...

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#10. Deuce Bigalow: Male Gigolo (1999)

Storyline: Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he runs into a male gigolo who asks him to look after his precious fish while he is away on business. However, he wrecks the house and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer his hot on his trail.

Plot Keywords: comedy, humor, romance, sexual innuendo, male perspective, absurd, exaggeration ...

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#12. Miss March (2009)

Storyline: A young man awakens from a four-year coma to hear that his once virginal high-school sweetheart has since become a centerfold in one of the world's most famous men's magazines. He and his sex-crazed best friend decide to take a cross-country road trip in order to crash a party at the magazine's legendary mansion headquarters and win back the girl.

Plot Keywords: comedy, teen, sex comedy, road movie, bromance, party, usa ...

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