Gossip Girl Episodes

2007, TV Show

Gossip Girl Episode: "The Sixteen Year Old Virgin"

Season 3, Episode 15
Episode Synopsis: Damien pressures Jenny to have sex. Meanwhile, Lily finally lets Rufus in on her huge secret; Chuck must make a tough choice concerning his hotel; and Dan and Vanessa try something new.
Original Air Date: Mar 22, 2010

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Season 3, Episode 15
Paid | iTunes
Length: 42:18
Aired: 3/22/2010
Also available on Amazon Instant Video and VUDU
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Gossip Girl Episode Recap: "The Sixteen-Year-Old Virgin" Season 3, Episode 15

Love and loss were themes on tonight's episode of Gossip Girl. On the love front, Lily and Rufus inched toward reconciliation, while Nate risked losing Serena when he let slip some unkind words. And on the loss front, Jenny considered losing her virginity, while Chuck faced the possibility of losing his hotel.

Dirty Dancing
Before this episode, Jenny had never seen Dirty Dancing and she had never had sex. By the end of this episode, one of those things had changed. A grounded Jenny was skipping school to see Damien in the mornings, but then she would retreat to Latin class whenever their make-out sessions progressed too far. Eventually, Serena fell into big sister mode and cautioned Jenny by relaying her own regrets and telling her that losing one's virginity is a big deal. Jenny explained that she really loved Damien and she thought he was the right one for her.

Then Serena slipped into Blair mode (assigning Nate the Chuck part) and schemed so that Jenny could see that Damien was a sleeze-ball. However, Serena and Nate are no Blair and Chuck, and Damien apparently really did like Jenny, because he resisted Serena's advances as he told her he was dating Jenny. Serena's plan totally fell apart, and Nate never intended to play along anyway. Instead, he acted like a snitch and called Rufus. Jenny was then under even more severe lockdown.

Since Rufus didn't trust leaving Jenny home alone, he took her to Chuck and Lily's party (the historical society was honoring Bart). At that party, Jenny ran into Damien and went off with him. Surrogate big brother Nate tried to stop this, and for that he got a punch in the face courtesy of Damien. The young lovebirds outsmarted everyone by booking a room at the Empire (the very same location as the party), and Jenny confessed to Damien that this would be her first time (he said he already guessed that). But because Damien dismissed this fact as being "no big deal," Jenny changed her mind about sleeping with him. A disappointed Damien then called her a "kid" and left her, and Jenny had to crawl back home and face everyone. She retreated to her room and listened to a song from Dirty Dancing (by now she had seen the movie and admitted it was "kind of good"), and when Serena asked her about how the night went, she lied and told her that she had sex with Damien and that "it was no big deal."

Say Anything
Playing a part in Jenny's ordeal caused Serena and Nate some strife. The biggest problem was that Nate said some things he shouldn't have: He didn't realize Blair had him on speaker phone when he was telling her Serena didn't understand that "losing her virginity is a huge deal for girl like Jenny." Serena then interpreted this to mean that Nate thought of her as "the concubine of the Upper East side" during her high school days. Nate ran through a list of guys (plus one art teacher) that Serena supposedly slept with in high school, and Serena was shocked he believed all of this, dismissing many of them as locker-room rumors. Then he brought up the fact that he loved her and lost his virginity to her, and when he woke she was gone and didn't return for a whole year. At that point, Serena realized that Nate wasn't trying to impose some double standard on her, but that she had hurt him after an event that was indeed a "big deal" in his life. And so these two cute kids made up.

As for Dan and Vanessa, they were trying to keep quiet about their relationship and not tell anyone. Dan then got into this whole "zone" thing with friend zones and classmate zones and friends-with-benefits zones. He offered to draw Vanessa a map to explain his complicated rules, but her solution was much simpler: She wore a really tight dress (and no underwear) to the party. Soon Dan was entering her dorm-room zone and telling her he was ready to try taking their relationship public.

Meanwhile, Lily was supportive of Rufus as he went through his struggles with Jenny. He remained stubborn and continued to shut her out, but eventually he came around and started to let Lily back in. They shared a kiss at the party and talked of starting from "a clean slate" when she returns from visiting CeCe. But based on Lily's phone conversation with her mom, the real reason Lily's going on a trip is to get some mysterious tests from her ex-husband, Dr. Van der Woodsen. Is Lily sick? There's definitely something she's not telling Rufus...

Risky Business
Things were not going well for Chuck with his hotel because of some bogus sexual harassment allegations raised by various female staffers (as Chuck explained, the old him would have been guilty of this, back when he was a kid at his father's hotel, but not the new him with his own hotel). He was willing to settle out of court in order to avoid a PR nightmare (as well as avoid telling Elizabeth about them), but the media and his new mommy got wind of them anyway.

Then things went from bad to worse: Uncle Jack reappeared on the scene, slimy as ever (but the new beard really worked for him, didn't it?). He was supposedly in town for the celebration in Bart's honor, but really, he was there to scheme. Then Elizabeth said something odd about the color purple — she claimed Bart loved it, when Chuck knew he loathed it. This, coupled with her resistance to meet Jack, had Chuck finally resulting to a DNA test (he should have done this in the beginning). Elizabeth was hurt by this mistrust, but the test results came back a match: She was indeed his mommy!

At this point Chuck's shady lawyer explained to him that Christian conservatives were threatening to boycott his hotel because of the lawsuits, so he needed to sign the place over (in name only) to someone else. Blair was too closely connected to him, and Lily was connected to Bass Industries. Jack volunteered, but Chuck was having none of that. So his only option was to sign over The Empire to his mom, Elizabeth.

In the final scene, Elizabeth answered a knock on her door: It was none other than Uncle Jack and Chuck's shady lawyer, and it was revealed that all three were players in a plot against billionaire boy Chuck.

So, are the DNA results accurate, or did the evil three have them altered? Did you feel bad for Jenny as she sat all alone in her room, or does she deserve a downfall? And what do you think is wrong with Lily?

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Love and loss were themes on tonight's episode of Gossip Girl. On the love front, Lily and Rufus inched toward reconciliation, while Nate risked losing Serena when he let slip some unkind words. And on the loss front, Jenny considered losing her virginity, while Chuck faced the possibility of losing his hotel. read more

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Premiered: September 19, 2007, on CW
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Premise: Privileged students in Manhattan keep up on local gossip from a secretive blogger who gets the scoop on everything and everyone. Based on the series of books by Cecily von Ziegesar.



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