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Do You Remember That "Gossip Girl" Threesome With Hilary Duff?

Three BuzzFeed writers take a look at this iconic episode of Gossip Girl and find out if it was really worth all the buzz it created.

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"They Shoot Humphreys, Don't They?" (Season 3, Episode 9) originally aired Nov. 9, 2009. It was directed by Alison Maclean and written by Amanda Lasher.

Ira Madison III: Obviously, the threesome is the biggest part of the episode. And we'll get to that in a bit, but first, let's see what the hell else happened in this episode.

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Ira: So, Jenny is planning for her cotillion date.

Sheridan Watson: Why is she figuring out her date ONE DAY in advance? That shit takes months to plan, you idiots. I mean this with the utmost respect: Why hasn't Jenny been thrown off of a cliff yet?

Ira: Are you familiar with the cotillion life, Sheridan? How realistic was this random evening they put on?

Sheridan: This is nothing like how my cotillion was. All of the cotillions I've seen involve white dresses, Amal Clooney gloves, perfectly choreographed routines, and people not randomly standing around looking at a lady announcing names like it's a goddamn sports lineup. But I'll give them the benefit of the doubt.

Kirsten King: I didn't have a cotillion. I bought a $50 J.C. Penney dress and went to a dinner dance so CAN I BE QUEEN B YET?

Sheridan: Can we talk about how vicious Jenny has gotten? Ah, high school, when you never realized how much of a bitch you were. I miss that total lack of self-awareness.

Ira: I love how random her bitchiness is, though? She reminds me of a basic version of Sydney Andrews from Melrose Place. She literally got her dream evening handed to her on a silver platter and then she was like, "Bye, bitch!" to Blair. What did you think was gonna happen to you?

Sheridan: You know better than to fuck with Blair Waldorf. I have to be honest: I liked Jenny at the beginning of the series. I was rooting for her. But as the seasons go on, you can't help but hope she gets sent off to live with her mother (lol). I think it's because the writers made her so damn desperate. When Blair schemes, it's necessary for the character. She's always been this vicious sort of person. Jenny, however, started becoming a bitch overnight, so it all seemed so random. All she does is say, "I'M THE QUEEN OF CONSTANCE, LOOK AT MY AWFUL SMOKY EYE. I RULE THE SCHOOL." OK, rant over.

Kirsten: Honestly, her smoky eye is the most problematic part of her character to me. I'm also really concerned about her extensions. How haven't they gotten caught in the subway, or revolving door?

Ira: I always root for the scrappy, underdog bitch character on soaps, but yeah, Jenny started acting too much like I assume Taylor Momsen was on set. Which is why she got canned after this season.

Sheridan: She was a teenager in real life working with 30-year-olds pretending to be her age. Guess a ~rebellious~ phase was bound to happen.

Ira: After Jenny gets taken down by Blair, she has no escort for the cotillion. So Nate steps in and she instantly becomes Queen B again. But like, she and Nate are friends. Why didn't she just ask him in the first place?

Sheridan: Because, Ira, that would be too realistic. We don't ask the important questions. Like how do the van der Woodsens function as a family? Why doesn't Rufus notice that his teenage daughter is becoming a disaster? When will Vanessa invest in better hair extensions?

Kirsten: OK. So here we have an 18-year-old Serena, working on a political campaign which she is in no way qualified for, with a conveniently sexy boss. But how the hell did Serena get hired for this damn job in the first place?

Ira: Tripp keeps talking about this "great opportunity" he's given Serena. Great opportunity for what? Does this heffa even want to work in politics?!

Sheridan: One sec, we just have to talk about the beauty that is Aaron Tveit. OK, second over. My favorite part of Serena's arc in this episode was when Tripp called Serena smart. Serena, as great as her wardrobe is, literally makes all the worst decisions ever. And then she pouts because she doesn't understand how her bad decisions keep on blowing up in her face.

Kirsten: Also how is Serena gonna walk into his office at 11 p.m. in a club dress and ask if he wants her to weigh in on his campaign plan?

Sheridan: Oh, and when she was like, "Why are you being so mean to me all of a sudden?" HE IS YOUR BOSS, HE IS NOT SUPPOSED TO BE YOUR FRIEND. You're also flirting with said married boss and then get upset when he wants to distance himself… Riiiiiiight.

Ira: She finally comes to the realization that her relationship with Tripp is inappropriate, so naturally, that entails heading over to his office in the middle of the night wearing a cocktail dress to tell him you quit. In person. Because an email wouldn't suffice.

Sheridan: That would make too much sense, Ira. And Serena never makes sense, she lives in a la-la land.

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Sheridan: I never truly noticed just how much Chuck squints. Like, I'm worried for his ophthalmologist.

Kirsten: Why does he always have that raspy just-woke-up/smoked-13-packs-of-cigarettes voice?

Sheridan: And I think we all need a moment of silence for the DEAD HOOKER on his couch. That actor is so good at fake sleeping that she actually looks deceased.

Kirsten: It's just so sad, because somewhere that girl is watching this Gossip Girl episode with her family saying, "THIS IS MY SCENE. THIS IS IT. THERE I AM!"

Sheridan: "Mom, I'm famous!"

Kirsten: Also like 90% of the time when you walk into Chuck's apartment there is a dead hooker.

Ira: But on the plus side, he looks so great in his purple pajamas.

Kirsten: Yes, despite the squinting and the casual case of black lung, he is still sexy.

Ira: Blair and Chuck spend so little time together for a pair of teenagers who are dating.

Kirsten: Right? And the only time they hang out is when they are plotting the destruction of someone else's life.

Sheridan: We do have to admit that this is a pretty cute episode for them. He's supportive, telling her that she loves cotillion and should be involved. He forces her and Serena to reconnect. She walks in and sees a dead hooker and doesn't even bat an eyelash. They're made for each other (except for when he sold her to his uncle for a hotel but semantics, amirite?).

Kirsten: You know shit's gonna go down because they're slowing fading in an acoustic version of "Whatever You Like."

Ira: Allowing that song was the worst crime Grand Hustle Records had committed until Iggy Azalea.

Kirsten: Also, if I get past the fact that Hilary Duff is like kinda still Lizzie McGuire in my eyes, she is totally sexy and I'm just saying…I would.

Ira: Hilary is totally banging in this episode. Penn Badgley is hot AF and I'm gay, so when the person I'm turned on the most by is Hilary Duff in your threesome, maybe you didn't do that good of a job, Gossip Girl.

Kirsten: Vanessa is just really jonesin' for any Dan action she can get, so she's like, "Eh, threesome will work."

Ira: Vanessa may quite possibly be the thirstiest character in the history of television.

Sheridan: I have a personal vendetta against Vanessa and Jenny — they gave hair extensions such a bad name. But do you guys remember when they teased the threesome for, like, 10 thousand weeks? And then the actual threesome was 10 seconds?

Kirsten: Right? Like how are they gonna cut back to cotillion and Jonathan's 5SOS haircut and leave us hanging like that?

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Ira: That promo…was a thing of beauty. This episode, however, isn't even in the top 10 as far as Gossip Girl goes, sadly.

Sheridan: Agreed. It was like 3 out of 10. There was no Waldorf bitchiness, and way too much Serena for my taste. Also, Rufus and Lily were just the worst parents ever in this episode.

Kirsten: Way too much Jenny. I prefer the episodes where she's visiting her mom in Buffalo. Overall, I wanted more Hil Duff, less everything else.

Sheridan: Amen.

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