The Significance of Teen Drama Characters Losing Their Virginity

Sexual awakenings are a huge part of growing up. They are also a huge part of the teen dramas.

At various points, the core six shows have depicted these critical coming-of-age moments as hypocritical, consequential, special, realistic, unrealistic, unfortunate, romantic, scandalous, and dramatic. Just as some of our favorite teen drama characters have gone on sexual journeys, looking collectively at the ways in which these shows tackled the subject of virginity is a journey too. Buckle up…

We begin, as always, with “Beverly Hills, 90210.” In episode 1.04, which is aptly named “The First Time,” Brandon (Jason Priestley) has sex for the first time with Sheryl (Paula Irvine), his girlfriend from Minnesota who visits Beverly Hills under less-than-honest pretenses. The scene in which they get it on is presented as something sexy, with Brandon’s suspicious mom Cindy (Carol Potter) fretting in another room about what her son may be up to. Husband Jim (James Eckhouse) isn’t concerned at all.

Contrast that with what happens with Brenda (Shannen Doherty) just months later. Brenda loses her virginity to Dylan (Luke Perry) in episode 1.21, “Spring Dance.” It’s depicted as a romantic, fun, and exciting milestone in Brenda’s life. But in the season 2 premiere, episode 2.01, “Beach Blanket Brandon,” Brenda worries she may be pregnant, and when Cindy discovers a pregnancy test in the trash, Jim essentially blows a gasket.

Not only is there a complete double standard in Jim’s reaction to Brenda losing her virginity versus Brandon, but unlike Brandon, Brenda is made to be regretful. She even ends up breaking up with Dylan, concerned their relationship moved too fast. But executive producer Charles Rosin initially intended to showcase Brenda as someone unashamed of embracing her sexuality. The plans were forced to change, however.

Rosin will be writing about what went down in his upcoming book, Beverly Hills, 90210: A Second Look, and gave me a sneak peek to share with you all.

“Fox asked for a cliffhanger to end Season #1 that could carry us into summer episodes to sustain the momentum we (‘Beverly Hills, 90210’) built as part of our triumphant, late-season ratings turnaround. 

Given all the ads for home pregnancy tests that flooded the airwaves, I thought the ultimate teenage cliffhanger would be is she or isn’t she pregnant. And I looked forward to the scene in our first summer episode based on a conversation with a girlfriend when we were in high school in the late ‘60s, who described the poignancy of being a daughter telling her father that she’s sexually active and not Daddy’s little girl no more.

Of course, to write that scene, the daughter had to become sexually active; hence, Brenda and Dylan fuck for the first time in a hotel room at the Spring Dance, off camera of course. Both had been AIDS-tested; Dylan would be wearing a condom. And, afterwards, back on the dance floor, Brenda would be wearing a smile on her face — unable to conceal her glee from Queen (of the Spring Dance) Kelly Taylor. That was intentional; after all, Brenda and Dylan were a fantasy couple for our core female audience — and there’d be no room for complaints that it hurt, or that the guy lasted a mighty 10 seconds, or that it was a bloody mess. No remorse. Just two teenagers making love and doing it right.

That’s what infuriated the reactionary Fox station owners, and other conservatives sampling the show their daughters had discovered during the Gulf War when Fox was the only network to run programming since, ironically, it was the only network not to have a news department. To say that these self-appointed guardians of the country’s morality were appalled by Brenda’s lack of remorse would be an understatement. The backlash from this mutually agreed story point overwhelmed the excitement of [‘Beverly Hills, 90210’ creator] Darren Star’s directorial debut — which captured our teen spirit and killed in the ratings — and would mark the escalation of a cultural war that that would set the tone for Season 2, and, for me, become an even more confrontational way to make television than what I had endured making the first twelve [episodes].”

Another character whose virginity was big deal on the show was Andrea (Gabrielle Carteris), who is tempted to sleep with Brandon in the season 1 finale, but doesn’t actually have sex until episode 4.06, “Strangers in the Night.” After they initially hold off, she loses her virginity to Dan Rubin (Matthew Porretta), a teaching assistant at CU, but their relationship ends shortly after and she begins another with Jesse (Mark Damon Espinoza) — and ends up pregnant. Like with Brenda, Andrea choosing to have sex is ultimately presented as consequential, and she’s embarrassed about getting pregnant. Donna (Tori Spelling) even tells her at one point, “A year ago, you were a virgin on your way to Yale. And then there was Dan and then Jesse and now you’re pregnant. I don’t think the girl you were a year ago would even recognize you now.”

Of course, there was no bigger virginity storyline for a character on “Beverly Hills, 90210” than that for Donna herself, as she famously planned to save herself for marriage. This decision was simultaneously presented as something admirable about her and something that negatively impacted her relationships with David (Brian Austin Green), Griffin (Casper Van Dien), and Ray (Jamie Walters). She seemed to have met her match in Joe (Cameron Bancroft), another virgin who wanted to wait for marriage, but Donna broke things off with him when he essentially proposed.

After coming close to having sex at various points over the years, Donna finally chooses to lose her virginity with David in the season 7 finale, episode 7.32, “Graduation Day.” Directed by Priestley, the episode ends with Donna basically presenting her lingerie-clad body to David. The moment feels special and the scene has gone down in teen drama history as one of the show’s most romantic. But there is something with which to quibble: “How’d I get so lucky?” David asks Donna when he finds her ready to give herself up to him. “You waited,” she replies. But David didn’t wait. Quite the opposite, actually. Frustrated with her unwillingness to have sex in season 4, David cheats on her and loses his own virginity to someone else. David rightfully faced consequences at the time — Donna didn’t hold back when dumping him — but it was like this part of their history was erased when they finally did sleep together years later.

“Dawson’s Creek” went the controversial route almost right off the bat, with the student-teacher affair between Pacey (Joshua Jackson) and Tamara (Leann Hunley). Despite an age difference of 21 years, Pacey is all too eager and happy to lose his virginity to his English teacher in episode 1.03, “Kiss.” Tamara faces no legal repercussions and merely leaves town after Pacey insists to the school board that nothing happened between them. To say this storyline hasn’t aged well would be an understatement.

Notably, after losing his own virginity under illicit circumstances, Pacey ends up being the loving partner when two of the show’s female characters lose theirs. First, Pacey and Andie (Meredith Monroe) discuss taking their relationship to the next level in episode 2.10, “High Risk Behavior,” with Pacey even getting STD testing and then being the one who suggests they ultimately hold off on crossing that line. It’s then revealed in episode 2.11, “Sex, She Wrote,” that they actually did decide to have sex, and while it initially seems Pacey is being a jerk to Andie in the aftermath in a “use ‘em and dump ‘em” kind of way, he actually confesses he’s fallen in love with her and is terrified of losing her. The entire thing is rather moving.

Then in season 4, it’s also moving when, after struggling with insecurities, Joey (Katie Holmes) confidently decides to sleep with Pacey in episode 4.14, “A Winter’s Tale.” In one of the series’ most romantic moments, Joey tells him all the reasons she’s sure this is the right decision, and there’s even a callback to one of their first kisses, with Joey counting down. After they awake the next morning in episode 4.15, “Four Stories,” Joey’s insecurities are back, but Pacey’s revelation that he’s insecure too ends up putting her at ease. For both Pacey & Andie and Pacey & Joey, the choice to have sex for the first time is carefully considered, the follow-up is insightful, and both relationships are ultimately strengthened.

“Dawson’s Creek” continues to combine first times with specialness in season 5, when Dawson (James Van Der Beek) loses his virginity to Jen (Michelle Williams) in episode 5.08, “Hotel New Hampshire.” What makes it so special is the full circleness of the moment. The series began with Dawson quickly becoming obsessed with Jen when she moves to Capeside. He has sex on the brain while Jen, because of her past, is in no rush to take things there. Their relationship in season 1 is ultimately short-lived and a brief hookup between them in season 2 looks like it might’ve led to sex but didn’t. That’s why it’s a true surprise when, years later, a moment of pure friendship unexpectedly turns into a beautiful moment of passion. Yep, “Dawson’s Creek” had meaningful on lock when it came to characters losing their virginity.

If “Dawson’s Creek” had romantic depictions of first-time sex largely covered, “The O.C.” excelled with realism. When Marissa (Mischa Barton) loses her virginity to Luke (Chris Carmack) in episode 1.06, “The Girlfriend,” she does so out of jealousy after walking in on Ryan (Benjamin McKenzie) mid-hookup with another woman. Her misguided determination to lose her virginity as some way to settle the score rings heartbreakingly true, as does her clear disinterest and discomfort with Luke. It’s a reminder that not every first time, even among couples, is special or romantic.

That was also driven home with Seth (Adam Brody) and Summer (Rachel Bilson) in episode 1.19, “The Heartbreak.” When the pair — who aren’t even an official couple at this point — have sex, it’s positively awkward. It’s even more awkward the second time. Seth, being a virgin and inexperienced, believes it’s all his fault. But Summer later confesses she, too, was a virgin, despite what most people believed about her. As a Bustle article stated last month, the storyline “showed the kind of clumsy, embarrassing first time sex usually reserved for real life.” Given what came before in the genre, it’s further asserted, “It’s The O.C. that at last depicted first times as they truly are: fast and uncomfortable.”

“The O.C.” and “One Tree Hill” premiered within weeks of each other in 2003, but they didn’t follow the same paths as far as virginity was concerned. Amidst the realistic depictions on “The O.C.,” “One Tree Hill” leaned more toward unrealistic. For Lucas (Chad Michael Murray), it was only somewhat implied — never explicitly stated — that he lost his virginity to Brooke (Sophia Bush) in season 1, though there is a pregnancy scare later on… one that she manipulates. Most glaring for being unrealistic, though, is what happens in the season finale, episode 1.22, “The Games That Play Us.”

At the end of the hour, Lucas discovers that Haley (Bethany Joy Lenz) not only slept with Nathan (James Lafferty) for the first time, but they’ve also gotten married. Haley had wanted to wait to lose her virginity until she wed, and, well, she and Nathan decided to tie the knot despite still being teenagers in high school. That’s not something anyone would categorize as normal or common. The following season’s premiere, episode 2.01, “The Desperate Kingdom of Love,” flashes back to how it all went down — Naley sleeping together and their nuptials — and features the reactions of each character’s parents. It’s strange to me sometimes how Nathan and Haley are held up as the ultimate “One Tree Hill” couple when the origins of their series-long marriage were anything but realistic.

Virginity is an even bigger topic on the show in season 4, with the introduction of Clean Teens — an abstinence group at Tree Hill High in which students pledge to remain virgins until marriage. It’s through this we first meet Shelley (Elisabeth Harnois) and Chase (Stephen Colletti), two of the club’s virginal members who become love interests for Mouth (Lee Norris) and Brooke, respectively.

Brooke and Chase end up happily sleeping together in episode 4.21, “All of a Sudden I Miss Everyone,” but things don’t go quite as smoothly for Mouth and Shelley. As it turned out, Shelley was actually a born-again virgin (having previously gotten pregnant and having an abortion). She was reluctant to sleep with Mouth, who is a virgin, but gives in in episode 4.14, “Sad Songs for Dirty Lovers,” and seems to regret it immediately afterward, which made me very sad for her. Perhaps that’s a realistic scenario, but it certainly didn’t reflect well on the characters. The whole thing feels… unfortunate.

It also didn’t reflect well in season 6, when Mouth and Millicent (Lisa Goldstein) are on the rocks and she’s driven to lose her virginity to someone else, Owen (Joe Manganiello), largely out of spite in episode 6.12, “You Have Got to be Kidding Me (Anatomy of the Devil’s Brain).” She confesses to Mouth in episode 6.13, “Things A Mama Don’t Know,” and in episode 6.14, “A Hand to Take Hold of the Scene,” in addition to being heartbroken by her cheating, Mouth essentially slut-shames her. Millie’s powerful response: “My virginity was mine, Marvin. It was never yours.” Again, it’s an unfortunate situation… to say the least.

Perhaps it’s an understatement to say “Gossip Girl” primarily went the scandalous route when it came to virginity. In episode 1.07, “Victor Victrola,” Blair (Leighton Meester) loses her virginity to Chuck (Ed Westwick) in the back of a limo despite being in an on-off relationship with Nate (Chace Crawford). (Meanwhile, Nate himself lost his virginity to Serena (Blake Lively) while cheating on Blair prior to the series’ start. Like I said, scandalous.)

Just a few weeks later, in episode 1.10, “Hi, Society,” Nate and Blair sleep together, with him wrongly under the impression it’s her first time. He doesn’t find out the truth until episode 1.13, “A Thin Line Between Chuck and Nate.” Both guys are upset with Blair, with Chuck even going as far as cruelly saying to her, “You held a certain fascination when you were beautiful, delicate, and untouched. But now you’re like one of the Arabians my father used to own: Rode hard and put away wet. I don’t want you now and I don’t see why anyone else would.” It’s a complicated take on virginity and a disgusting one too.

But it gets worse. The younger Jenny (Taylor Momsen) loses her virginity to Chuck in the season 3 finale, episode 3.22, “Last Tango, Then Paris.” This is the same Chuck who tried to rape her in the show’s very first episode. To make matters worse, Blair’s reaction is to punish Jenny for this, effectively banishing her from Manhattan. I’m just going to be blunt: It’s all so fucked up on so many levels.

When Dan (Penn Badgley) loses his virginity to Serena in episode 1.11, “Roman Holiday,” it’s so tame and beautiful in comparison. As a Christmas gift, Serena creates an indoor winter wonderland, which provides the lovely setting, and Dan’s Christmas gift for her provides the romantic impetus. She even vocally gives her consent. There’s no twist, no fallout, no drama. There’s just a happy ending, in more ways than one.

When it comes to virginity on “90210,” we start with Silver (Jessica Stroup) and Dixon (Tristan Wilds), both virgins who consummate their relationship in episode 1.16, “Of Heartbreaks and Hotels.” It’s a Valentine’s Day-themed installment and there is clear consent and even an obvious use of protection, but casting a shadow over the momentous moment is Silver’s brewing struggles with bipolar disorder, which come to a head a couple of episodes later.

Mental illness is also looming in the background when Annie (Shenae Grimes) loses her virginity to Jasper (Zachary Ray Sherman) in episode 2.09, “A Trip to the Moon.” While having sex is her idea and she believes they’re in love, Annie is unaware at this point of Jasper’s manipulations — or the depths he’ll go in the future to control her, including a suicide attempt. (Read my 2010 interview with Sherman about this storyline here.)

Unbeknownst to Navid (Michael Steger), it’s not really a great situation when he loses his virginity either. There’s a slow-burn to this, with Navid first telling the experienced Adrianna (Jessica Lowndes) that he’s never had sex before in episode 1.10, “Games People Play.” Taking things slow is quite alright with her, but when they do finally sleep together in episode 2.04, “The Porn King,” Navid has no idea Adrianna is largely motivated out of guilt after kissing Teddy (Trevor Donovan). That situation blows up a few episodes later.

And because it’s apparently a trend on “90210,” the circumstances surrounding Ivy (Gillian Zinser) losing her virginity aren’t ideal either. First off, despite wanting her first time to be with Dixon, she ends up having sex with Oscar (Blair Redford) in episode 3.05, “Catch Me If You Cannon,” after being unaware of the real reason Dixon has pushed her away — he may have contracted HIV and, obviously, did not want to risk giving it to her.

Ivy only learns the truth after she and Oscar have done the deed, and then to make matters worse, in the next episode, she finds out Oscar has been sleeping with… her mom. I’ll be blunt again: It’s so fucked up. And it’s certainly off-putting that every “first time” on “90210,” even if it seems nice in the moment, ends up stemming from or building to a dramatic twist.

So, what have we learned? What is the significance of teen drama characters losing their virginity? Well, on “Beverly Hills, 90210,” we have moments cloaked in double standards and consequences. On “Dawson’s Creek,” when we put aside the actual crime committed with Pacey and Tamara, such moments are special and meaningful. On “The O.C.,” they’re realistic. On “One Tree Hill,” they swing between unrealistic and unfortunate. On “Gossip Girl,” it’s only romantic for Derena; otherwise, it’s all about scandal. And on “90210,” it’s drama, drama, drama.

They are all significant in their own ways, but there is no throughline, as I see it. There’s no clear evolution with a teen drama building off the groundwork laid by the one that came before it. Even with all that the shows have common in one another, what with relying on the same genre tropes, they largely had different styles when it came to this ever-critical aspect of growing up.

And it makes me wonder what the upcoming “Gossip Girl” spinoff will contribute to the subject. Will losing one’s virginity still be a big deal? And if so, will it be presented in a hypocritical, consequential, special, realistic, unrealistic, unfortunate, romantic, scandalous, or dramatic way? Only time will tell and, I, for one, am increasingly eager to find out.

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