Billboard in a New York City subway station Credit: Therese Shechter

There was a time when Therese Shechter, like most people, thought of virginity as a fairly simple concept. You had it, you lost it, you told a story about it. Then she started working on her documentary, How to Lose Your Virginity, which makes its Chicago premiere November 2, and realized it was ridiculously complicated.

“We’re fascinated with the idea of virginity,” she says. “And that fascination is so wrapped up in history and religion and pop culture. We all go through something. It’s a primal adolescent experience.”

The accepted definition of a virgin is someone who has not had sex. But what counts as a first sexual experience? Many people might say intercourse. But what if the penis doesn’t get all the way in? And what if you’re not heterosexual? What if you have oral sex? Anal sex? Does masturbation count? What if your first experience with intercourse wasn’t consensual?

“Once you start picking it apart, it doesn’t make much sense,” Shechter says. “It’s based on nothing solid whatsoever. The idea of virginity is ephemeral. It doesn’t hold up to any scrutiny at all.” Not even medically, she finds: the whole thing about the hymen is total bunk.

Diagram of a hymen from a 1940s educational filmCredit: courtesy Trixie Films

Shechter worked on How to Lose Your Virginity off and on for nearly seven years. The leisurely pace was unintentional: documentaries are expensive and she needed to take breaks for several rounds of fundraising. But the long pauses gave her time to think more deeply about the subject of virginity and assemble a collection of interviewees with a wide range of perspective and experiences: Ellen, a former evangelical Christian whose first penis-in-vagina sexual experience was on her wedding night and was truly, traumatically awful; Brita and Dan, a couple whose decision not to have intercourse before marriage doesn’t preclude them from experimenting with lots of other forms of sex, including a set of graduated dildos; Meghan, a transwoman who wonders what sex will be like now that she’s in a female body; Sarah, a comedian who has made her virginity part of her standup routine; and Erica, the producer of the Barely Legal series of pornos whose own “first time” was a rape.

She also talks to a group of college students who believe that it’s OK for a woman to have sex before marriage, but not too much sex. “What about if you’d had 30 partners?” Shechter asks one from off camera. The young man looks horrified.

“It’s as if there’s some metric,” Shechter says now. “Because you have a relationship with ten different penises, that makes you dirty and no one will love you. But that idea is very emblematic of the way we talk about sex.”

Shechter includes footage of a debate at Harvard University between Lena Chen, a sex blogger, and Janie Fredell, a member of a campus abstinence group, in which the two women unexpectedly discover common ground. “The story about women and sex becomes a battle over who is more worthy of love. Their entire personality is defined by their sexual choices. The most important part is [the perception] that the woman from the abstinence group is more worthy of marriage and love.”

Therese ShechterCredit: Anneliese Paull

(Shechter herself fails an on-camera reenactment of a medieval virginity test, administered by Hanne Blank, author of the book Virgin: The Untouched History. It involves measuring the circumference of her head and neck. Off camera, Shechter’s fiance laughs hysterically.)

Since Shechter completed the documentary and took it on the road, she’s been hearing many, many more stories about virginity lost and virginity recovered and virginity defined. She’s collected about 300 of them on a website called V-Card Diaries. “We’re always given one narrative, one ‘right way,'” she says. “You don’t want to get it wrong. But you go to the site and there are 300 different stories and different experiences.”

She’s most gratified when adults approach her after screenings to tell her the film made them rethink their own first sexual experiences. “They say, maybe it wasn’t first intercourse, but when I had my first orgasm,” she says. “Or maybe they say, it happened, but it wasn’t the biggest deal. I like when people do that.”

How to Lose Your Virginity will be showing Mon 11/2, 7:30 PM, AMC River East, 322 E. Illinois,, $12. Advance tickets only.