What Made It Awkward? Ah, where to begin. One could start with the fact that year-old Telly Leo Fitzpatrick is guppy-macking on a year-old girl. Or that she seems scared and unsure about going through with the sex part, but Telly is fleecing her like a pro, grooming her with all of the sweet nothings in his arsenal, so that her virginity can become his prize. Or that the bedroom in which their nubile, half-naked bodies writhe looks like that of a typical year-old girl — Laura Ashley bedding, stuffed animals on the dresser, a ballerina music box on the shelf — because, as I mentioned, the face that Telly is sucking is that of an actual child. This scene is even more chilling in hindsight, because later in the film, we find out that Telly is spoiler alert knowingly HIV positive, and yet he still pressured this girl, and who knows how many others, to have sex with him. Reckless does not even begin to describe his behavior; predatory is more like it. Exclusive Features.

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To celebrate the 10th anniversary of Judd Apatow's blockbuster hit The 40-Year-Old Virgin
A day in the life of a group of teens as they travel around New York City skating, drinking, smoking and deflowering virgins. Disturbing, dark, low-budget independent film about teen-agers in New York City. The story focuses on Telly Leo Fitzpatrick , a teen who has a goal to de-flower as many virgins as he can. When one of his old encounters discovers that she is H. Kids follows a group young, unsupervised, not mature, but all-too-grown-up kids in New York. One girl has just been diagnosed with HIV and is trying to notify the boy who gave it to her, who is on a quest to sexually prey upon innocent girls. The film follows these characters and their friends through the day, hanging out, playing, carousing and going to parties.
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When Amanda was 26 years old she found herself in a familiar but awkward situation: She was still a virgin and the guy she had been dating for three months didn't know it. She wasn't ready to sleep with him yet, but she was close, real close. One night they were at his house, making out on the couch, when he asked her, "When's the last time you had sex? She didn't know how to answer, and she didn't really want to.
On celluloid, sex is easy, wild, and overflowing with orgasms. What is this sorcery?! It helped that The Year-Old Virgin was really funny and oddly sweet. Unfortunately, many of those characters were often defined by their virginity in ways that stigmatized the very act of celibacy. Some films got it right, though, capturing the excitement and fear that accompanies your first time, which is, more often than not, an awkward affair. But what makes this scene more cute-awkward than creepy-awkward is that William, though stunned, is clearly receptive to the idea, and also that the object of his affections, Penny Lane Kate Hudson does not participate. What Made It Awkward? Her age, for one. Dawn is only 11, and, as played by the pitch-perfect Heather Matarazzo, deeply uncomfortable in her own skin.