The best virgins and deflowering moments in cinema...feature film cinema that is

    With Sex Week upon us, what better time to reminisce about or imagine our first times? In no particular order, we proudly present the best movie virgins and deflowering scenes.

    The 40-Year-Old Virgin

    This movie is probably one of the first to pop into anyone’s head at the mention of “virgin.” The title makes the plot of this movie pretty obvious. Andy is on a quest to get laid because he is 40 years old and, in some eyes, way past due for his first time. The number of condoms he tries to put on for that first time is sure to get you cackling — not to mention the kids walking in. The 40-Year-Old Virgin contains one of the most humorous depictions of deflowering in any movie, making it just fine to laugh at that first time, even if you are 40.

    Better Off Dead

    Lane Meyer reminisces in the middle of math class over the first time he had sex with his ex-girlfriend Beth, who he is still completely obsessed with. The sex took place in his station wagon in the middle of the woods. Meanwhile, you could see black silhouettes robbing the tires off Lane’s car. Oh so romantic.

    Lane: “That thing I put on me… it broke.”
    Beth: “Broke? It BROKE??”
    Lane: “Take it easy, I’ll buy you a new one!”
    Beth: “I don’t WANT a new one! Do you know what that MEANS?”

    But I’m a Cheerleader

    But I’m a Cheerleader is a hysterical commentary on sexuality and gender. The plot of this movie revolves around sexuality. Peers and family of cheerleader Megan Bloomfield think that she is a lesbian because she doesn’t like kissing her football-star boyfriend, and so they send her off to a special rehab center called True Directions to “convert” her into a heterosexual. Of course, Megan ends up meeting Graham and falling in love with her, all while trying to “become straight” in a backdrop of ridiculous gender role activities and crazy pink/blue color schemes. The sex scene between Megan and Graham is rather romantic and tender, quite a contrast with the ridiculous environment in which the two reside.

    Cruel Intentions

    This movie is so erotic it hurts. Not to mention a little bit messed up. Err, a lot. Virgin Annette is set on waiting until love for her first time. Meanwhile step-siblings Kathryn and Sebastian make a bet surrounding Sebastian’s ability to get Annette into bed. In contrast with the rest of the movie’s lies and manipulations, Annette’s first time with Sebastian is quite sweet and loving. Sebastian asks “Are you okay?” while Counting Crows’ “I Am Ready” plays, showing his true feelings for Annette despite his initial intentions. This is definitely a romantic sex scene, an interesting juxtaposition with all of the lustful, erotic interaction between Sebastian and his other female suitors.

    American Pie

    The entire plot of this movie revolves around four friends trying to get laid for the first time. American Pie is probably most notable for the infamous pie scene in which character Jim Levenstein inserts his penis into a “warm apple pie”, to see what oral sex with a woman feels like. Awkward. This movie leads up to several deflowering scenes, but the pie scene will always be the most memorable and out of the ordinary. Actor Jason Biggs has said in interviews that he is often heckled about the pie scene by fans and will always be remembered as “the pie fucker” in Jay and Silent Bob Strike Back.


    With a name like McLovin, how can you not get laid? While this awkward but adorable geek technically doesn’t quite lose his virginity due to being cock-blocked by the cops who bust the high school party, he still manages to miraculously coerce a beautiful bombshell into bed with him to do the dirty deed — impressive for someone of his stature.


    Mary always planned on waiting until marriage for sex. One day, she gets what she believes is a sign that Jesus wants her to have sex with her boyfriend Dean so that he will become straight. I don’t think I will ever get over the trophies clumsily banging and clunking against the wall in this sex scene. It’s a reasonably fair representation of the uncertainty of teenage deflowering, which is out of character in the glamorous world of Hollywood sex. The scene is complete with an awkward white bra and a strange, insecure conversation following intercourse — who hasn’t been there? (Scene starts at 8:04 mark in the video below.)


    This movie is brilliant. Disturbing, but still quite genius. When Dawn O’Keefe’s boyfriend forces her to lose her virginity, Dawn gets the ultimate revenge by ripping off his penis. How? Vagina dentata. For those who don’t know, vagina dentata is an urban legend of a woman’s vagina having teeth, probably a stranger facet of the premarital sex taboo. This film questions what would happen if vagina dentata actually existed. It also examines how they empower Dawn, who turns the tables on the men who sexually violate her.

    Sixteen Candles

    What is greater in a teen movie than the nerd getting laid? Ultimate win for nerds everywhere. Ted, the token geek in this film, makes a bet with his friends that he can have sex with his love interest, Sam. While he never reaches this goal, he manages to nab Carolyn, the prom queen, after driving her home in her intoxicated state. Though the sex scene is just implied in their conversation the morning after, Ted’s ability to seal the deal is nothing short of phenomenal. Oddly enough, Carolyn seems to have fallen for him after just that one night, making him the ultimate conversion from total geek to hot stud.


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