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I Had Sex Like Serena Van Der Woodsen From 'Gossip Girl' For A Week

I had sex like Serena from Gossip Girl

Hey there, Upper East Siders. I wanted to do something very “scandalous lives of Manhattan’s elite” to honor the return of the series.

But because I can’t jet off to Spain with some guy I just met or write a best-selling novel spilling all my influential friends’ dirty secrets, I figured having sex like Serena van der Woodsen would be the next best thing.

She might not have the same iconic one-liners as Blair, and no, she doesn’t get it on in the back of a limo or with a teacher in the costume closet, but what Serena lacks in comebacks, she makes up for in being, well, Serena.

After pulling out a plaid skirt and consciously choosing not to brush my long, blonde hair, I studied a few of S’s most salacious situations to create a week’s worth of sex fit for the true queen of the Upper East Side. The days I wasn’t going at it, I was busy falling in love with people after one conversation and shit-talking my friends on a blog. (You know, Serena stuff!)


The good news: You don’t have to wait to read about my experience in a Gossip Girl blast. Here are all the dirty details surrounding my week of Serena sex. You know what they say: Good news travels fast, but scandalous news travels faster….

First up, recreating Serena’s bar sex

First with Nate at the Sheppard wedding, then with Dan at the Sheppard divorce party, it’s clear S was a big fan of having bar sex that would absolutely ruin her friends’ lives. But since I didn’t have my bestie’s boyfriend on hand, I had to use my husband for this situation.

After seductively pulling my hubs over to our bar (yes, we built a bar during COVID-19 because we are basic millennials) and not-so-casually spilling on him—which was Serena’s classic move—we started making out against the bottles.

I hoisted my body onto the bar and wrapped my legs around my husband’s torso. When Serena and Nate have sex on the bar, it’s very much a “this is wrong, let’s not do this” situation, so in order to give off the same vibe, we kept our windows open so if our neighbors happened to look over, they might catch a glimpse of us groping among our shot glasses.


After using a large amount of lube (because unlike Serena, I’m not exactly ready to go after a few seconds of rushed foreplay), we had quick, kinda-uncomfortable-because-the-height-difference-was-weird bar sex that felt almost as liberating as if I were doing it with my best friend’s boyfriend and not with the man I married.

Dan and Serena’s romantic snow sesh

There’s not a lot of romantic sex in Gossip Girl, but when Serena and Dan finally consummate their relationship in season 1, it’s about as close as the show gets to hearts and flowers.

While I intended to surprise my husband with an impressive winter art installation in our living room just like Dan did, I didn’t have “elves” to help me (or any of Blair’s minions, for that matter), plus I lack upper-body strength. So I asked my husband to help me make a fort in our living room.


After he did 98 percent of the work, I turned the A/C down to 60 degrees, played a “romantic snow” video on YouTube, and threw some crushed ice at my hubs to let him know that (a) we were going to fuck in a fake winter setting and (b) I needed him to warm me up.

At first, he wasn’t game since he said, and I quote, my fingers “felt like frozen, dead-person hands.” After I agreed to put on a pair of mittens, we had a few minutes of strange gloved foreplay in our living room fort. (No, it wasn’t as romantic as S and D’s first time, but giggling under some blankets while I stroked our bodies with my mittened hands was actually kind of sweet?)

By the time I was trying to undo his buttons with my hands, we were a blissful mixture of aroused, giddy, and connected. The different temperatures from the ice and air conditioning and the texture of the mittens made for a unique experience as he held my gloved hands down and caressed me to the sound of falling snow.


Two words: Bathroom! Sex!

Even though riding on the Jitney from the Hamptons to New York is about the least Serena thing ever, it happened. And while S was on the bus, she casually fell into Dan’s lap and the two snuck off to the teeny-tiny bathroom to talk about their feelings! Probably!

Whatever they were doing in there, my hubs and I were not about to go on a random bus trip on the off chance we’d be able to sneak into the (probably smelly) bathroom to (maybe) have sex. In order to sort of recreate the pair’s spontaneous hookup, I decided pulling him into the powder room at our friend’s Fourth of July BBQ was as good as it was going to get.

Once we locked the door behind us and started drunkenly making out, it was clear this was as dire of a situation as it was for Serena and Dan. Within minutes, someone was already knocking on the door saying they needed to pee. While I’m not sure what position Serena and Dan managed to pull off, with a line of people waiting to use the bathroom and just enough liquid courage to deal with their complaints, we had quick, quiet sex over the sink with my face pressed against the mirror and his body pumping behind me.


No, it wasn’t romantic or even that good, but walking out of the bathroom with “just fucked” hair and disheveled clothes felt very on-brand for my Serena week.

Serena’s kitchen feast with Nate

Even though Nate and Serena aren’t my favorite pairing (there’s just something so “meh” about them), their kitchen hookup *did* make for one of my favorite sex scenes of the OG series. The couple went at it while eating breakfast in such an iconic fashion that I’ve actually tried to recreate it before.

The first time my husband and I tried to have sex in the kitchen with berries, waffles, and whipped cream à la S and N, it went horribly. After trying to flirtatiously throw some whipped cream at him, my husband went into schoolyard bully mode and pelted me with food while our dogs barked in the background and tried to lick our sticky skin.


Still, I figured with a little more preparation and fewer sticky substances, we could pull it off. Instead of trying to ease into the situation, I made it very clear what would be happening: First, the whipped cream would go on my body, then he’d feed me strawberries, then I’d have about seven orgasms—all before 9 a.m. and all while standing naked on an old shower liner in our kitchen.

While I wasn’t passionately hoisted into the fridge where we fed each other caramel
and olives (seriously, gross), and the tarp gave things a slight serial killer vibe, it was still a fun way to start our morning. After taking turns licking whipped cream off each other, we quickly had floor sex before diving into the bowl of berries, which promptly got blood-like juice all over the shower liner turned tarp.

Role-playing like Serena

As everyone knows, Serena became “Serena” and Gossip Girl became “Gossip Girl” in ninth grade on a school trip. After Serena got water spilled all over her while wearing a white dress, she became GG’s pervy inspo and thus the infamous blog and Serena’s celeb status was born.


Since Serena’s sexcapades are kinda slim pickings (she’s more about quantity over quality), I figured mixing her white dress moment with her love of role-playing at bars with Georgina Sparks would be a fun way to close out my week.

After donning a thin white dress, I stood in the shower for a minute to get the fabric soaking and see-through. Once I was sufficiently wet and regretting my decision, I called my husband into the bathroom to “help” me.

Upon finding me standing in the shower in a wet dress, he immediately asked if I was okay. Once I started talking in a Southern accent and asking if he “comes there often,” the panic switched over to full-blown confusion. I muttered something like, “Just, it’s a thing, okay?” and he slowly stripped down and joined me in the shower.

While I’m not sure if Serena ever went home with a guy after pretending to be “Savannah,” I’m pretty sure she didn’t stand fully clothed in the shower before freaking her partner out and having quick bent-over-the-tub sex. But! I can’t be sure, so who’s to say?


The verdict

Out of all the original Gossip Girl characters, Serena might be the most notorious, but her sex situations are a little dry. Call me old-fashioned, but I’d rather have back-of-the-car sex with an older, married woman than fake-snow sex with my on-again, off-again high school boyfriend. While S might be the Upper East Side’s eternal It Girl, here’s hoping the new cast has a little bit spicier sex lives. XOXO.


This article originally appeared on Minor edits have been made by the editors.