The Sixteen Year Old Virgin is the fifteenth episode of season three and the 58th episode overall.
From the day he brings his newborn girl home, a father lives in fear. That someday she'll get hurt, that someday she'll hate him, and worst of all, that someday she'll grow up.
Jenny and Damian consider taking their relationship to the next level but Serena is determined not to let that happen. Meanwhile, Dan and Vanessa try to figure out what their relationship actually is and Chuck, facing a big lawsuit, tries to find a way to trust his mother.
Jenny is leaving for school when Rufus reminds her of his rule: she to school and she comes home. As she leaves the loft, she calls for a car to pick her up and take her to The Smith Hotel, where Damian is staying. At The Empire, Blair invites Elizabeth to go shopping and mentions Chuck has something to ask her. Elizabeth is excited, and tells Blair that the week together has been wonderful. Chuck returns from a meeting with his lawyer, and explains that several employees at The Palace are suing him for sexual harassment. Chuck's lawyer adds that they have proof that two of the girls weren't even in town on some of the alleged nights and Blair is confident they can win. Chuck replies that since a court case would be a PR nightmare, they have to settle. Blair says that it isn't fair, and Chuck tells her that since Bart is being honored that night, he doesn't want a scandal to overshadow the night. She asks Chuck if he's doing it for Elizabeth and he says no, but Blair insists that it's okay if he is. She tells him that there isn't a point in having her around if he isn't going to let her in, and that not everyone is willing to wait years for an I love you.
Lily comes to the loft looking for an update on Jenny. Rufus explains that their agreement is that she goes to school, comes home, and doesn't date boys involved with drugs. Lily is about to ask Rufus something when Headmistress Queller calls to inform Rufus that Jenny didn't show up for school and has been cutting classes all week. Meanwhile, Nate and Serena wake up in Blair's bed at the Waldorf's. Rufus texts Serena, asking if she knows where Jenny is because he thinks she's with Damian. Serena tells Nate that Damian tried to kiss her and that Rufus not allowing Jenny to see him is making her like him more. She announces she's not going to let that happen. At NYU, Dan, after spending the night with Vanessa, is avoiding Rufus. Vanessa tells him that he's going to have to talk to him eventually, and Dan says he isn't sure he wants to explain where he's been. He eventually calls Rufus back, but he's more interested in finding Jenny than in Dan's whereabouts. At The Smith Hotel, Jenny and Damian are making out when he starts to feel her up. She gets up quickly and says she has to get to school. Damian tells her that if she's not cool with having sex with him, it's fine, but she needs to say something instead of making excuses and asks if she's a virgin. Jenny insists that's not what she's trying to do, and that she doesn't like the first time with someone to be rushed, before saying she isn't a virgin. Damian tells her to sneak out that night when Rufus goes to bed, and Jenny agrees.
Chuck, Elizabeth, and Blair are out shopping and Chuck invites Elizabeth to come to the gala that night honoring Bart. Elizabeth immediately says yes, saying that this is why she's here, to be a part of Chuck's life and Chuck smiles. At that moment, reporters run up demanding answers to the lawsuit. He tells Elizabeth that it's a lie and whispers to Blair that someone must have leaked the story. As they're walking away, Chuck receives a call from his uncle Jack and realizes he must have been behind the recent events. Back at the loft, Lily tells Rufus that Jenny cutting school to be with her boyfriend isn't criminal behavior. He admits that he just hopes that the real Jenny is still somewhere inside her. Lily decides to ask Rufus to put the past in the past, and says they need to talk. She invites him to the gala that evening, and he declines, saying he's not quite in the mood to celebrate one of her exes. Rufus then goes to the back to call Serena again, and Lily leaves, but not before leaving the scarf Rufus left at Holland's on a desk.
At the Waldorf's, Serena has invited Jenny to come over. They eat ice cream and discuss Jenny's relationship, and Jenny reveals their plan to have sex that night. She asks Jenny if she's a virgin, and she admits she is. Serena tells her that once she loses her virginity she can never get it back and asks if she's sure if Damian is the right guy, and Jenny says he is. Serena says she'll support her either way, and volunteers Nate to take Jenny to lunch. At the Empire, Jack goes to see Chuck, claiming he only wants to protect him. Chuck is suspicious, asking Jack if he really expects him to believe he showed up at the same time the lawsuit did. Jack replies by telling Chuck that he heard the Evelyn Bass has risen from the dead. Chuck says that she was never dead and Bart paid her to stay away. Jack tells him that he saw Evelyn's body in the casket at the funeral home, and that he never got along with her, and that maybe that will change if she comes to the gala. On his way out, he runs into Blair. He informs her that Chuck will have to step down, and Blair says that Jack will never get it.
At the Waldorf's Serena recaps her plan to Nate. While he's with Jenny, she invited Damian over for lunch in anticipation that he would try to have sex with her again. Nate says they should just tell Jenny, but Serena is positive her plan will work. At the loft, Dan tells Rufus that Jenny's forbidden guy phase is normal. Rufus mentions how Dan's been sleeping out a lot, and Dan brushes it off. Vanessa shows up to help look for Jenny, and Dan proposes a map of friends with benefits versus just friends zone. She says no, but Dan still insists they talk about boundaries. While talking to Damian, Serena lies and says she and Nate are no longer a thing and she has no feelings for him. Damian rejects her, saying he's with Jenny and actually likes her. He says he's sorry about Nate and leaves. Serena tries to call Nate, but he ignores the call. Jenny is confused about what's taking them so long to leave when Rufus arrives at the restaurant to get Jenny.
In Brooklyn, Rufus angrily tells Jenny the new arrangement. He will escort her to and from school, Headmistress Queller will assign someone to walk class to class with her, and she will eat lunch in her office. Jenny demands to know why she's being treated like a child, and Rufus says that by bringing Damian and his drugs into the house she is acting like one. Jenny yells that he always jumps to conclusions that's why his marriage is failing and storms off. When she leaves, Rufus sees the scarf Lily left behind. At The Empire, Elizabeth arrives to see Chuck. She presents him with a new purple necktie, and says that Bart loved purple too. Chuck admits that he only wears purple because Bart loathed it, and Elizabeth replies that Bart was always playing games with people's heads. Chuck brings up Jack, and Elizabeth asks if she's coming to the party that night. He replies that he's not invited, but he'll probably sneak through the cracks. Elizabeth tells Chuck that her and Jack have ugly history and she doesn't have the strength to deal with him and meeting Lily and his family that night. Chuck asks her to stay for a drink then, since she won't be coming to the party and she says yes.
At the Waldorf's, Serena and Blair are getting ready for Chuck's party. Nate calls and Blair answers and puts him on speaker phone. He says that Serena might not get it, but losing her virginity is a big deal to a girl like Jenny. Serena takes offense and hangs up on him. At the loft, Rufus sees Jenny watching Dirty Dancing. He tells her that he needs to go to the gala to talk to Lily and has to take Jenny because he can't trust her alone. Outside The Empire, there's a crowd of protestors. Blair arrives at Chuck's penthouse and sees him packaging a glass that Elizabeth used. She figures out he's planning to conduct a DNA test and is disappointed in him. He points out that she shows up out of the blue, doesn't know things about Bart, and when she hears Jack is coming to the party, she bails. Elizabeth overhears, as she came to tell Chuck she changed her mind. Chuck is still insistent on a DNA test, and she tells him that he is his father's son and leaves. Blair decides just to meet Chuck there.
At the gala, Serena is still angry at Lily for being with Dr. Van Der Woodsen when she came to see him. Lily wants to talk but Serena isn't interested and walks away. Chuck approaches Lily and the two hug. Chuck, loving Lily as his own mother, thanks her for coming. Upstairs, Nate and Serena talk. They argue until Nate says that the morning after he lost his virginity to her, he found out that she had left town and had a good reason for going behind her back and saying what he did. Jack tries to talk to Lily when Rufus comes up and tells him to leave her alone. He does, and Lily says he must have found the scarf. He asks her if they can talk alone. Dan arrives and talks to Jenny about Damian. Their conversation is cut short when Dan spots Vanessa wearing a strapless dress. He goes over and tries to kiss her, but she reminds him this is a friends only zone and walks away. At the same time, Nate decides he should talk to Jenny. He tells her about Damian trying to kiss Serena at the state dinner (in The Hurt Locket). She says she already knew and he only did it to get the jacket Serena was wearing with the drugs inside. Nate quickly figures out Damian must be dealing and tells Jenny she can't date someone who deals. Damian arrives and Jenny jumps up to meet him. Nate catch up with the two and tells him there's no way he can leave with her. Damian then punches Nate, also knocking over a waiter before the two leave. Dan and Vanessa witness the fall, and Serena runs up and Nate tells the three of them that Jenny left with Damian and that he's a drug dealer. Serena tells him where he's staying and Nate goes off to find them. While talking, Rufus admits to Lily that he almost slept with Holland to even the score but he loved Lily too much to go through with it. They are about to kiss when Dan comes over to tell Rufus that Jenny left with Damian.
Chuck is sitting alone when his lawyer comes to tell him that things have taken a turn. He tells Chuck how the Family Travel Council is organizing a boycott. Chuck is fine with the idea, saying that will only increase his clientele. His lawyer reasons that the hotel doesn't have the luxury of waiting around to see, and suggests Chuck hand over operations of the hotel for PR. Jack volunteers himself, and Chuck informs him that no matter what, that will never happen. Jack says he'll wait and when The Empire is bankrupt, he'll swoop in and buy it for a fair market price. Chuck asks if that was his plan all along and he says no, but he's going to reap the rewards. Meanwhile, Nate arrives at The Smith Hotel and discovers Damian's room is empty. Damian and Jenny are actually at The Empire. Blair goes to see Chuck and learns that he's going to have to sign the hotel away. Blair volunteers, and Chuck says that Blair running it is not a good idea. She suggest Lily, but Chuck says that since she's Bass Industries, she's not an option because he doesn't want his father's company bailing him out. At that moment, DNA results come in and Chuck says he officially has another option.
At The Empire, Jenny confesses to Damian that she's a virgin. Damian says that it's no big deal, and Jenny realizes that it is a big deal to her. He again brushes it off, and she decides she doesn't want to do it anymore. He leaves, telling her he knew she was just a kid. At the loft, Rufus, Lily, Dan, and Vanessa are waiting. Lily says the police are looking but aren't optimistic they'll find them that night, and Serena says they weren't at The Smith. Jenny comes home and tells everyone she and Damian broke up. She asks if she's still grounded and when Rufus says yes, she goes to her room. Serena follows her and asks if she's okay, and Jenny says yes. She assumes they didn't do it, but Jenny lies and says they did. She also tells Serena that it wasn't a big deal and asks her to shut the door when she leaves.
Elizabeth is packing her suitcase when Chuck arrives at her hotel room. He apologizes for not trusting her, and confesses that it's hard for him to let people in. She says it's understandable, since she abandoned him when he was a baby. He asks her to take over the hotel and she hesitantly agrees. At the loft, CeCe calls Lily to tell her that it's time to check in with Dr. VDW. Lily agrees and says she'll be on the next flight. She lies to Rufus and tells him she's going to Canyon Ranch. He says it's a good idea and they agree to have a clean slate when she returns. The two hug, and Lily tears up. Dan goes to see Vanessa at the dorm, and they decide to start officially dating and to tell people. At the Waldorf's, Nate and Serena apologize to each other. She says she never meant to hurt Nate, and that she wishes they could relive their first time because now they know they love each other. At The Empire, Blair is waiting for Chuck. She tells them they're going to celebrate themselves; Chuck for opening up to his mother and herself for encouraging him to do it.
Jack and Chuck's lawyer arrive at Elizabeth's hotel and ask if they have themselves a hotel. Elizabeth says they do and it's revealed the three of them were working together to steal The Empire.
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald
- Taylor Momsen as Jenny Humphrey
- Ed Westwick as Chuck Bass
- Jessica Szohr as Vanessa Abrams
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Laura Harring as Elizabeth Fisher
- Desmond Harrington as Jack Bass
- Caroline Lagerfelt as CeCe Rhodes
- Kevin Zegers as Damien Dalgaard
- Rockstar 101 by Rihanna (ft. Slash)
- So Light is her Footfall by Air
- Gospel by The National
- (I've Had) The Time of My Life by Bill Medley and Jennifer Warnes
- Hungry Eyes by Eric Carmen
- Good Life by One Republic
- I Party by Far East Movement (ft. IZ and DB Tonic)
- Trampled Youth by Kid A
Blair: Settlements are for the guilty. Celebrities who run people over, the Catholic Church. It's not fair!
Jenny: It's 9:30, I have Latin.
Damian: It's a dead language, it's not going anywhere.
Jack: I would have been here sooner but I got distracted reading some of those protestor's signs. I never realized how many sex puns you could make out of the name Chuck Bass.
Rufus: If she was a vampire, I could sneak garlic in her waffles. Not that she'd eat them.
Blair (on Serena's Damian plan): It seems pretty reasonable to me.
Nate: Yeah, because it's a Blair Waldorf nut job plan.
Jenny (to Dan): And when you were sixteen you were in love with Serena and everyone thought it was adorable.
Chuck's lawyer (on the lawsuit): We're getting attacked by Christian conservatives,
Chuck: We have those in Manhattan?
Chuck (to Elizabeth): I don't trust other people. Those other people aren't my mother.
- The episode title is based off the movie The 40-Year-Old Virgin.
- The Hulk - Rufus compares The Hulk to Jenny's anger.
- Turnbull and Asser - Chuck mentions how Prince William and himself put the manager's daughter through college.
- Prince William - Chuck references the prince when explaining the hospitality at Turnbull and Asser.
- New York Historical Society - The library is going to donate a room to Bart.
- Patrick Swayze/Dirty Dancing - Serena tells Jenny to watch the movie and later Jenny is seen watching it on her laptop and listening to the soundtrack.
- Christian Louboutin - Blair mentions the designer.
- CBS - Blair tells Chuck he's been watching too much of the channel.