There are some unforgettable ‘firsts’ in a person’s life: first day of school, first kiss, first job, first car, first breakup and, of course, first time having sex. TBH, any brand-new experience can be seriously stress-inducing, but no matter at what age it happens or who you do it with, losing your virginity can be an especially daunting/exciting/confusing time. Coming-of-age films can help us navigate new experiences as we grow from tweens to teens to adults and even if they are fictional — they make us feel like we’re not total weirdos for wanting to do absolutely normal things.
Having sex for the first time is such a personal decision and there’s only one person who can tell you if you’re ready: YOU. Sometimes, however, seeing characters on the big screen figure out what feels right to them in the sex department can add a bit of clarity to your own personal decisions. While we’ve seen characters like Emma Roberts in Valentine’s Day work hard to swipe her v-card with her high school BF on a romantic holiday, the whole movie isn’t focused entirely on that storyline. That being said, we decided to only include flicks on this list that are first-time centric, as opposed to ones that have virginity-loss as a more minor subplot.
The First Time
How can you not love a movie starring a sensitive Dylan O'Brien and a spunky, outspoken Britt Robertston? Not only did their characters fall in love while filming The First Time, a film basically about waiting to have sex for the first time until you find the right person, but the two actors did IRL, as well!
Photo: Samuel Goldwyn Films
Very Good Girls
Lots of guys in these movies make pacts with their bros to lose their virginity before a certain time, but in VGG it's actually two young women who decide they'll both have sex for the first time over the summer. The film has a star-studded cast and features a strong female friendship, which automatically gives it some brownie points in our book!
Photo: Universal Pictures
The Rules of Attraction
Ian Somerhalder and James Van Der Beek both star in this comedy about having sex for the first time. While it's a heavier film than a lot of the others on this list (one of the main characters, a virgin, gets raped in the beginning of the film, and another character attempts suicide), it explores different ideas surrounding casual sex and shows people of various identities (including LGBTQ+) figuring out their sexuality at a young age.
Photo: Kingsgate Films
The three dudes in Superbad have three goals: get alcohol, party a lot, and have sex. However, for as funny as the film actually is, it drew criticism for glorifying rape culture.
In the movie, the guys getting alcohol is seen as a necessity in their ability to do the deed, which many thought suggested that they would have to get the young women drunk enough for them to agree to have sex — and as we know, consent can't be given once a person is inebriated. It's definitely a controversial subject as many said the necessity for alcohol wasn't for the girls, but actually just so they would be allowed in the party. Either way, it's a hilarious film, but it's def important to watch with a critical eye.
Photo: The Apatow Company
The 40 Year Old Virgin
The film's title should basically sum this one up for you. Basically, when his three co-workers find out that Steve Carrell's character, Andy, has never had sex despite being 40 years old, they decide to help him finally get some. Prepare for some serious laughs!
Photo: Universal Pictures
Sixteen Candles has a lot of other stuff going on besides Sam Baker's (Molly Ringwald) desire to lose her virginity to her hot, senior crush, but the virginal status of several teenagers in the film is definitely a central topic of discussion during the whole of the movie.
Photo: Channel Productions
Cruel Intentions is a movie about a stepsister and stepbrother who make a bet over the latter's ability to deflower a young woman who has an article in the paper about how she's waiting for marriage to have sex. If he succeeds, he gets to sleep with his stepsister, Kathryn (huh?!). If he doesn't, however, she gets his car. That seems....fair?
Reese Witherspoon's virginal character is tough and strong-minded and she refuses to be a conquest. But, as per usual in a rom-com, everyone's feelings become muddled and complicated and she must decide if she really wants to stay abstinent after all.
Photo: Columbia Pictures
This absurd comedy is the classic 'group of dudes make a pact to lose their virginities before high school graduation' plot line, but just so happens to have spun off seven sequel films!
Photo: Universal Pictures
The To Do List
Like Very Good Girls, this virgin-centric film talks about the pressure for girls to have sex before going to college. Aubrey Plaza's character wants to have as many sexual experiences as she can before heading off to university, which means making her summer goal to have sex with her high school crush... after experimenting sexually with other guys first. Also starring Rachel Bilson and Bill Hader, this bad boy is a rom-com that you don't want to miss!
Photo: Varsity Pictures
The Virginity Hit
Matt Bennett, from Victorious, is about to lose her virginity to his girlfriend, Nicole, until he finds out that she cheated on him. So his friend, played by Zack Pearlman, decides that Matt should have sex with her anyways — but must let him record it... for his documentary. Creepy.
It received fairly poor reviews (possibly because there are some WEIRD plot lines... one involving Matt's adoptive sister trying to have sex with him) but the film should basically teach you what not to do when losing your virginity.
Photo: Gary Sanchez Productions
Fast Times at Ridgemont High
Like American Pie, this is yet another desperate-for-sex teenager film — but when it came out in 1982 it was a *little* controversial because it featured an abortion scene! The scene was cut when released in theaters, but added again when the film made its way onto TV. It's also so random that Sean Penn plays the main character with long, blond locks.
Photo: Refugee Films