The 10 Most Memorable Plans To Lose Virginity In Movies

Losing one's virginity can be a Herculean task in real life, and even more difficult in movies. Cinema has long depicted hapless men and women going to incredible lengths to join the ranks of the sexually active. There have been countless horny teens and one unforgettable 40-year-old virgin, but nobody like real-life poet, journalist, and polio patient Mark O’Brien.

In the indie drama The Sessions, John Hawkes portrays O'Brien, who is paralyzed from the neck down and dependent on an iron lung to breathe, but nonetheless strives to lose his virginity before he dies. He attempts to achieve this through the use of sex surrogate Cheryl Cohen Greene (Helen Hunt), who is hired to be his first. It’s an incredibly heartfelt and powerful look at the struggles of a man trying to come to terms with himself and his own disabilities.

Not all on-screen virgins' quests are as challenging or emotional as O'Brien's, but many are nonetheless impressive. To help prove that, and perhaps make a few struggling virgins' plight feel less like "mission: impossible," Complex counts down The 10 Most Memorable Plans to Lose Virginity in Movies.

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Written by Jason Serafino (@serafinoj1)

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Sex Drive certainly wasn’t brilliant, but it did show the desperate lengths teens will go to ensure that they don’t enter college as virgins. In the movie, young Ian (Josh Zuckerman) takes a road trip with his friends so he can meet up with, and sleep with, a woman he met online named "Ms. Tasty." He does this so he can lose his virginity quickly, even though the girl of his dreams, his friend Felicia (Amanda Crew), is on the trip with him.

Of course Ms. Tasty is nothing more than a front by a man and woman who steal cars and sell them to chop shops for a living. Even so, the risk was well worth the reward, as Ian winds up having sex with Felicia afterwards. All it took was an attempt on their lives to make them realize that they loved each other.

In The Virginity Hit, four teens buy a bong and make a deal that it will be used only when they’ve lost their virginity, so as you can plainly see, the stakes were pretty high here. Each helpless teen in the movie has a scheme to cash in their v-card, but the plan for Matt (Matt Bennett) is the most memorable. As he is the last virgin among the group, his friends take the liberty of contacting his favorite porn star, Sunny Leone, to have sex with him for a hefty price.

Paying a large sum of money like that to accomplish your goal might seem like cheating, but if it’s good enough for the Yankees, it’s good enough for a group of teenage virgins. In the end, Sunny convinces Matt not to lose his virginity to her, but instead to somehow that he actually loves, which he then goes on to do. It’s a rare ray of positivity in what's otherwise a smut-fest of a film.

We’ll say it up front: Losin’ It is not a very good movie; in fact, it's downright awful. It was made during a time when sexually-charged ‘80s comedies were all the rage, and it was about as humorless as an Ingmar Bergman film. But it did feature Tom Cruise memorably taking a trip to Tijuana with his other virgin friends in search of some loose women to score with.

Soon enough they stumbled upon a woman, played by Shelley Long, who went along with them so that she could get a quick divorce from her husband. It’s not a memorable movie, but it’s a memorable premise. Plus, it hit theaters during a simpler time when Tom Cruise was a complete nobody, as opposed to the alienating megastar that he is today.

When an ultra-Christian named—believe it or not—Mary Cummings (Jena Malone) finds out that her boyfriend Dean (Chad Faust) might be gay, she decides to sacrifice her virginity in an attempt to turn him straight after a vision of Jesus tells her to. Despite Mary’s attempts at a horizontal rebirth, his parents still find gay porn under his bed. Dean is promptly sent to a Christian treatment center where he is to be reprogrammed.

Unfortunately, Mary’s encounter with Dean leaves her pregnant and without a baby daddy to support her. In short: This plan works for nobody involved, but it sure made for an entertaining hour and a half.

In this smutty ‘80s gem, a group of virginal high school kids travel to Porky’s, a local bar, in an attempt to take advantage of the establishment’s legendary prostitution ring. But they soon learn the hard way that losing your virginity takes a lot more hard work than just paying a hooker to do the job for you. They also learn that dudes named Porky probably shouldn't be trusted.

Though at first Porky (Chuck Mitchell) attempts to turn the boys away at the door, he quickly comes around and takes their money for what the boys think will be a high-priced lady of the night. Instead, he dumps the teens off in the swamp in the middle of the night, leaving them to fend for themselves. The movie then turns into a revenge tale as the boys try to figure out a way to get back at the surly bar owner and his crooked cop brother. As you can see, the quest for sex is serious business.

When Andy’s (Steve Carell) co-workers realized that he is a 40-year-old virgin, they conspire to change the way he dresses, acts, speaks, and grooms himself in order to finally get him laid. But things don't work out at first as Andy attracts a dirty-talking nymphomaniac and a booze-swilling tramp while taking their advice. Things finally start to look up when he meets his true love, Trish (Catherine Keener), who he eventually marries while still a virgin. And he does so while ignoring the plan his co-workers put in place for him.

Unfortunately, their first time rolling around in the marital hay lasts about as long as a sneeze and the grim reality of premature ejaculation temporarily ruins this glorious moment. Thankfully for Andy, he quickly regains his stamina and gets it right the second time. If there is anything that a 40-year-old virgin would understand more than anyone, it's the art of persistence.

In order to impress their dream girls and lose their virginity at the biggest high school party of the year, Evan (Jonah Hill), Seth (Michael Cera), and Fogell (Christopher Mintz-Plasse) plan to use Fogell’s fake ID to score beer and supply the fiesta with beverages. Unfortunately, after going to great lengths to get alcohol, Evan and Seth strike out repeatedly at the party, and Fogell comes close to getting lucky but is interrupted by cops barging in.

You would think that a couple of kids who were almost killed on multiple occasions while trying to bring beer to the party would have been able to score with just about anyone, but the road to virginal hell is paved with good intentions and these three seemed damned to continue their sexless escapades for a bit longer.

Obsessed with losing his virginity before the end of high school, the class wigger, Kenny (Seth Green), a.k.a. Special K, arrives at a party packing a bag of sex supplies, such as boxes of condoms and a copy of the Kama Sutra. But his plans for losing it seem hopeless as he finally lines up a desperate girl, then goes to a bathroom to practice sex positions, and gets locked after Denise (Lauren Ambrose), a former friend, walks in on him.

Fortunately for Kenny, awkward chit-chat turns into soul-baring and leads to the two having sex in the bathroom, proving that it’s not always a bad thing when the best laid plans of mice and men go awry.

When high schoolers Kevin (Thomas Ian Nicholas), Chris (Chris Klein), Jim (Jason Biggs), and Paul (Eddie Kaye Thomas) hear that the class nerd lost his virginity before any of them, the teens make a pact to all lose theirs before graduation. But the outcome is an absolute mess, as they all strike out more often than A-Rod in clutch moments, and find out that Sherman lied about his sexual exploits in the first place. Once that weight has been lifted off of their shoulders, the members of this troupe go on to all lose their respective virginities after the prom.

The plan didn't go the way they thought—especially for Jim, who had his masculinity stripped from him after a woeful web cam calamity—but they wind up all smiles at the end. Since American Pie hit theaters, the virginity pact plot has become commonplace in TV shows and movies, but this one still stands out among the rest.

When a 38-year-old polio patient (John Hawkes) in an iron lung wishes to lose his virginity before his eventual death, he is convinced to get in touch with a sex surrogate (Helen Hunt) who will do the deed for him. This is probably the most awkward plan to lose one’s virginity that we have ever seen, but it’s also incredibly touching because of the fact that it’s done in such a sensitive and innocent manner.

Based on the real life story of journalist and poet Mark O’Brien, this plan is a refreshing change of pace from all of the horny teenage virgins that we usually see in movies. Even the most jaded audience member should feel something while watching this man try to achieve something that most people take for granted.