Pop Culture's Most Beloved Virgins

In Cruel Intentions, virgin Annette actually published a manifesto stating that she wouldn't have sex until she was in love. Womanizing Sebastian makes a bet with his stepsister that he can make Annette one of his conquests, and they eventually fall in love and consummate the relationship. But a tragic accident prevents a happily ever after.

She may be obsessed with Sex and the City, but Shoshanna is the only virgin out of the Girls foursome. But the self-described "least virgin-y virgin ever" loses her v-card by the end of the show's first season to an unlikely candidate.

Aubrey Plaza plays Brandy Klark in the '90s-set film The To Do List. Brandy's a recent high school grad who's trying to lose her virginity (amongst other sexual experimentation) before she heads off to college. I won't give anything away, but she must make the classic decision to have her first time be with the hot, aloof dreamboat or the sweet, best guy friend.

Despite pretending to be slutty and talking a big talk — even telling Jane, "You're way too uptight about sex" — high schooler Angela Hayes of American Beauty is really just an insecure virgin.

The film The Sessions is based on the true story of Mark O'Brien, a journalist and poet who was paralyzed from the neck down by polio and had lived in an iron lung for much of his life. Nearing 40, he decided to hire a sex surrogate to help him lose his virginity.

Overachieving surgeon April in Grey's Anatomy didn't get her nickname "Virgin Mary" for nothing. But her sexual status changes when she decides to sleep with a friend and fellow Seattle Grace surgeon the night before her medical board exams.

Max just can't catch a break! While trying to impress his crush, the new kid in town accidentally brings back the witchy Sanderson sisters in Hocus Pocus. As he's reminded throughout the entire film, all the trouble started because "a virgin . . . lit the candle."

In Glee's aptly titled "The First Time" episode, Kurt is ready to lose his virginity to his first boyfriend, Blaine. We were all rooting for the inexperienced gay teen to find love — go Kurt!

In For a Good Time, Call . . . , phone sex operator Katie drops a major bomb when she admits that she's a virgin — even with all the dirty talk. She may know what to say in the bedroom, but can she do the deed?

Our favorite sensible bookworm, Rory of Gilmore Girls, decides to have sex for the first time with her first love, ex-boyfriend Dean. The only problem? He's now married.

In order to play the coveted starring role in Black Swan, virgin ballerina Nina Sayers needed to let herself go . . . in more ways than one.

Blair is a virgin in the first season of Gossip Girl, choosing not to sleep with Nate. But virginity is no match for Chuck Bass. She loses it to him in the back of his father's limo.

Edward, the 108-year-old virgin, finally (spoiler!) becomes a man — er van? — in Breaking Dawn Part 1 when he and Bella have the most anticipated vampire-human sex ever. And, yes, of course they're married.

Cher, the other virgin of Beverly Hills, held out for her stepbrother, famously saying, "You see how picky I am about my shoes and they only go on my feet."

Donna Martin saved her virginity until college graduation night, as all good Catholics do.

Poor Andy. After 40 years of waiting, he finally loses it on his wedding night.

After lying to fellow-virgin Dawson about her virginity, she finally loses it on a ski trip to Pacey.

Since the only girl that could probably get George Michael to do it is his cousin Maebe (but maybe not!), he remains a virgin for all of Arrested Development's three seasons, and in just about every movie he's made since.

Perhaps nobody ever deserved to lose his virginity more than American Pie's Jim Levenstein!

In The CW's hit show Jane the Virgin, Jane has vowed to stay celibate until marriage but still manages to get pregnant when she is accidentally artificially inseminated with the sperm of her former crush.