Photo-Illustration: Vulture

There are a few key milestone episodes that crop up in every teen show, if it lasts long enough: the graduation, the first big breakup, the huge fight with a friend, the drinking/doing drugs/betraying one’s parents, and, of course, the losing your virginity episode. The virginity plot has been handled both clumsily and gracefully over the years, and the passage of time hasn’t necessarily led to more progressive storytelling. In 1988, Natalie lost her virginity on The Facts of Life, and things were more or less fine. Twenty years later, on the premiere of The Secret Life of the American Teenager, Amy gets pregnant after her first time (when she’s not even sure she had sex). Cory and Topanga waited for marriage, but it’s not clear if Winnie Cooper and Kevin Arnold did.

In honor of our High-School-TV Showdown, Vulture decided to look back at some of the more memorable characters’ first times, from The O.C. to Gilmore Girls. Over the years, we spotted some consistencies in how TV shows view the big moment. Characters still drop lines like, “Now I’m a woman/man,” and worry they’ll be a loser if they don’t go through with it. They grapple with being ready. It’s still seen as a bigger, more serious deal for a female character. Where it differs is that nowadays, it’s more strange to be a virgin than not past a certain age. And sometimes, the decision to have sex is met with relatively few consequences. Sex can just be sex. But above all, these shows tend to agree: It’s a big freaking deal.

Natalie and Snake, The Facts of Life

When: “The First Time,” Season 9, Episode 16 (February 6, 1988)

How It Went Down: On the anniversary of the day they fell in love, Natalie and Snake do not want their night to end. Cut to Natalie looking at herself in the mirror knowingly.

Consequences: Snake says he’s too busy to hang out with Natalie for a while. At first she’s distraught, but Natalie ultimately decides she’s not upset she had sex – she’s upset that Snake is being weird. At the end of the episode, he visits her to say he’s ready to really commit because, obviously, they’re going to get married soon. She tells him to pump the brakes because she’s not 100 percent sure yet. Everyone is fairly shocked that Natalie had sex, but they don’t judge her too harshly for it.

Carlton and Joann, The Fresh Prince of Bel-Air



When: “It’s Better to Have Loved and Lost It …,” Season 4, Episode 5 (October 11, 1993)

How It Went Down: After a randy afternoon at the Tom Jones Museum, Carlton is smitten. He asks Joann to marry him, which makes her laugh, then asks if he can give her a kiss good-bye. She replies, “Yes, tomorrow morning.” The audience responds like it’s the best line in the universe. Cut to a tunnel, a bunch of fireworks, a dog catching a Frisbee.

Consequences: Joann was actually married, so Carlton ends up pretty heartbroken. But Will apologizes for making fun of Carlton for being a virgin so much and pressuring him to have sex.

David and Donna, Beverly Hills 90210



When: “Graduation Day: Part 2,” Season 7, Episode 32 (May 21, 1997)

How It Went Down: Writer and executive producer Larry Mollin told Vulture that they kept pitching episodes where Donna lost her virginity, but because she was played by Aaron Spelling’s daughter, it got delayed. Finally, in the season-seven finale, she loses it. There are candles and sappy music, and Donna’s wearing white lingerie. “How’d I get so lucky?” David asks. “You waited,” Donna replies.

Consequences: None. It’s basically what a preteen’s fantasy of losing your virginity would be.



Buffy and Angel, Buffy the Vampire Slayer



When: “Surprise,” Season 2, Episode 13 (January 19, 1998)

How It Happened: Buffy and Angel are their typical, brooding, star-crossed-lover selves in this episode. They think they’ll be separated for a while because Angel needs to bring a demon’s arm to the “remotest region possible.” Cue a scene with tons of yearning on the docks, where Angel gives Buffy a claddagh ring for her 17th birthday. Later in the episode, Spike and Drusilla threaten to kill Buffy and Angel, but they get away in time. After running in the rain, they make it to Angel’s apartment, wet from the rain, where they consummate their relationship.

Consequence: Angel turns into Angelus, the version of himself without any humanity, because he experienced a moment of pure happiness. He torments Buffy and the gang for the rest of the season. In the finale, just as he gets his humanity back, Buffy has to stab him. So, it basically goes as poorly as possible.

Felicity and Eli, Felicity

When: “The Fugue,” Season 1, Episode 16 (March 2, 1999)

How It Happened: Felicity and Noel’s relationship hits a rough patch when his ex-girlfriend Hanna (Jennifer Garner) reenters his life. On a rainy night, Noel almost hooks up with Hanna, but stops. Meanwhile, artist-type Eli (Simon Rex) and Felicity start hooking up after Eli volunteers to draw Felicity. He asks her if she wants to stop. She shakes her head, “No.” End of episode.

Consequences: A lot of emotional turmoil for Felicity and Noel. Felicity says, “My first time was with someone I didn’t know, and I’ll never be able to change that.” She calls it a mistake, but mostly because she hurt Noel. At the end of the next episode, they break up.

Cory and Topanga, Boy Meets World

Episode: “The Honeymooners,” Season 7, Episode 8 (November 12, 1999)

How It Happened: Even though they’ve been together since they were kids, Cory and Topanga still don’t have sex until after they’re married. Eric gives a speech at the reception where he presents the couple with a hotel key that Cory instantly accepts, dragging Topanga away from everyone. The audience screams and hoots with excitement. Topanga says there’s such a thing as foreplay, but Cory rips off his suit, ready to go. They take off all their clothes in bed, only to be interrupted by the police and arrested. Turns out it wasn’t actually their hotel room. They just have sex on their honeymoon.

Consequences: Aside from the arrest, life carried on for the newlyweds.

Eric and Donna, That ‘70s Show

When: “The First Time,” Season 2, Episode 16 (February 14, 2000)

How It Happens: Eric helps Donna write the vows for her parents’ wedding renewal. Having to write them reminds Donna how much she’s in love with Eric, and she’s tells him she’s finally ready to have sex.

Consequences: None.

Ephram and Madison, Everwood

Episode: “No Sure Thing,” Season 2, Episode 14 (February 9, 2004)

How It Happens: After her first boyfriend Colin’s death, Amy had a pretty rough season. So when promos teased that either Ephram or Amy was going to have sex, all fingers were crossed that it was Ephram and Madison, the babysitter (Amy’s potential partner was bad news). Madison mentions that her roommate is leaving, and that means they’ll have the place to themselves that weekend. Ephram, being a teenage boy, is absolutely certain this means sex. But not before a few false starts. Ephram tries to get things going at her apartment, and she tells him to leave. Later, they have a sweet talk and decide to go for it, only for Ephram to finish before they start as she’s reaching over him to get condoms. The magic finally happens when they’re talking in his car, trying to pick a song, and Ephram’s able to get her belt off (a problem that first time).

Consequences: None immediately. But she does eventually get pregnant and give the baby up for adoption. Ephram’s dad keeps it from him, and it becomes a huge and devastating story line.

Seth and Summer, The O.C.



Episode: “The Heartbreak,” Season 1, Episode 19 (February 18, 2004)

How It Happens: The time is right for these two adorable weirdos. Seth broke up with Anna when he was unable to hide his feelings for Summer. He goes to her room and relays the kind of heartfelt lines only teens can say, like, “For me, it’s always been you, Summer.” He becomes transfixed basically as soon as she takes her top off. Later, he tells Ryan, “I sucked so bad, I was like a fish, flopping around on dry land.” Sandy tells Seth about foreplay. The couple tries again. It’s limbs everywhere and bad again. At the end of the episode, Summer admits she was also a virgin. They both decide they rushed into it.

Consequences: Bad sex. But otherwise, no consequences.

Haley and Nathan, One Tree Hill

Episode: “The Games That Play Us,” Season 1, Episode 22 (May 11, 2004)

How It Happens: In the previous episode, Haley searched for “Origin of Species” on Nathan’s computer, and this showed up:

She later finds some suggestive images of Peyton on his computer. They fight. “I gave you my heart,” Haley said. “That’s all that I can give to you.” Cut to this episode, where they make up and Nathan says Haley is “clearly threatened by a sexual relationship.” By the end of the episode, they’ve eloped and had sex. High-school marriage is a loophole for abstinence.

Consequences: Now that they’re married, they have to deal with everything that comes with that commitment. Their marriage is rocky, but they’re still together at the end of the show, so decide for yourself how dark this story line is.

Rory and Dean, Gilmore Girls





Episode: “Raincoats and Recipes,” Season 4, Episode 22 (May 18, 2004)

How It Happens: After an almost-kiss early in the episode, Dean tells Rory it’s over with his wife, Lindsay. They get busy in her childhood bed.

Consequences: The worst thing ever: Lorelai’s disapproval. “I didn’t raise you to be like this,” she tells Rory. “I didn’t raise you to be the kind of girl who sleeps with someone else’s husband.” It’s terrible and sad. End of season. Eventually Lindsay finds out, and there’s a traumatizing double-mother-daughter confrontation in the middle of the town.

Blair and Chuck, Gossip Girl



When: “Victor/Victrola,” Season 1, Episode 7 (November 7, 2007)

How it Happens: Blair and Chuck have sex in the backseat of a limousine at the end of “Victor/Victrola.” By the next episode, Blair is confessing her sins in church: “After being broken up with my boyfriend for exactly 20 minutes, I succumbed to inebriation, performed at a speakeasy, and surrendered my virtue to a self-absorbed ass.”

Consequences: Blair and Chuck become the show’s definitive couple. They get married in the finale, and the show later redefines their first time as Blair losing her virginity to her true love.

Kurt and Blaine and Rachel and Finn, Glee



Episode: “The First Time,” Season 3, Episode 5 (November 8, 2011)

How it Happened: Artie tells Rachel and Blaine they need to lose their virginities so they can play Tony and Maria in West Side Story with more passion. Rachel and Finn are about to have sex, but she admits that she just needs to lose it before opening night so she can act better, which upsets Finn. Meanwhile, a drunken Blaine tries to get Kurt to have sex with him, and it’s a huge turnoff. After the performance, Rachel and Blaine make up with Kurt and Finn, and both couples have sex because they want to, not because of West Side Story.

Consequences: None.

Stiles and Malia, Teen Wolf



Episode: “Echo House,” Season 3B, Episode 8 (February 24, 2014)

How it Happens: Stiles has been given a very temporary reprieve from being possessed by a dark spirit, while Malia was recently turned human again after being a coyote for most of her life. They kiss, and it’s Malia’s first. Stiles asks if she wants to try again, and they kiss again. “I want to try something else,” Malia says, and takes off her shirt. Some fans still weren’t 100 percent sure what went down, but the implication is there.

Consequences: They immediately get tortured, but that was a foregone conclusion. The sex was more of a respite from the horror show that is these teens’ lives.

Stefan and Valerie, The Vampire Diaries

When: “The Age of Innocence,” Season 7, Episode 3 (October 22, 2015)

How It Happened: A recent entry! Sure, you might have assumed that Stefan lost his virginity to Katherine, but nope, it was Valerie, a newly introduced heretic, who took his V-card. The two meet at a fair and have instant chemistry. Then she takes him into the woods, and … well, it’s hard for TVD characters not to have sex in the woods. She later writes to him and tells him she wants to run away with him. But Valerie doesn’t show up to meet him when she said she would.

Consequences: An unplanned pregnancy! Plus, an evil guy named Julian beats her so that she loses the baby. We haven’t fully seen this story line play out, but in the present day, it’s probably going to cause a lot of issues between Stefan and Caroline. Stefan had never mentioned Valerie before this season, but because she’s his first, the show imbues their brief tryst with great significance.