Blake Lively as Serena van der Woodsen in The CW's 'Gossip Girl'
Here Are The Best Sex Scenes From The Original Gossip Girl

These steamy moments are imprinted on my brain.

by Christy Piña and Rachel Varina
Originally Published: 

There might be a new batch of corrupt teens darkening the halls of Constance Billard, but it’s hard to compete with the original Gossip Girl cast. While the HBO Max reboot, which debuted on July 8, 2021, is pretty solid, there’s just something especially scandalous about the OG series. The far-fetched plotlines and hot characters are iconic, but it’s the romances that really set the show apart. No matter how raunchy the new version gets, these sex scenes from the original Gossip Girl will remind you why The CW’s show is so legendary.

When the first episode of the series aired in 2007, fans immediately fell for Blair's understated evilness, Serena's perpetual party-girl vibes, Nate's good looks, and Chuck's bad-boy demeanor. And while yes, the characters themselves are memorable, it was the fact that these scandalous teens were hooking up everywhere and with everyone that really made the original series so damn sexy.

The truth is, few teen shows have quite as much salacious sex as the one and only Gossip Girl. From Nate and Serena at the Shepherd wedding to Dan and Serena at the Shepherd divorce party to Blair and Chuck in the limo, here’s a peek at some of the moments that had the Upper East Side talking back in the early 2010s.


Dan & Serena’s First Time

After almost a full season of getting so close to having sex, Dan and Serena finally hooked up during Season 1, Episode 11, “Roman Holiday.” When they agreed to limit the amount of money spent on their Christmas gifts to each other, Serena set up a snow simulation, which is where they finally got it on. As one of the only really romantic hookups in the season, what it lacked in steam it made up for in sweetness.


Serena & Nate At The Shepherd Wedding

Ah, the infamous Shepherd wedding, which set off a series of scandalous situations. During the pilot episode of the series, Nate and Serena were sent away by Blair to "sober up," and instead, they ended up having sex right on the bar. No, it’s not the hottest sex scene (and it’s kinda cute how dated it seems now), but it was a defining moment in the series that followed the characters through to the finale.


Serena & Dan At The Shepherd Divorce Party

If you feel like you’re having déjà vu, you’re not wrong. In a totally twisted move, Serena got Dan to cheat on Blair in the same place she got Nate to cheat on Blair in Season 5, Episode 24, “​​The Return of the Ring”. What turned this situation up even more is that she tried to film it (without his consent) which was the cherry on top of the “this was majorly messed up” sundae.


Blair & Chuck In His Limo

The CW

Season 1, Episode 7 set the tone for Chuck and Blair's infinitely whirling, on-again, off-again relationship. In "Victor, Victrola,” the two hooked up for the very first time after Chuck watched Blair dance onstage alongside the dancers at his new burlesque club. Even though Blair was still involved with Nate, she had spontaneous sex with Chuck in the back of his limo, which she tried — and failed — to keep secret from everyone, including Gossip Girl.


Dan's Infamous Threesome

Whether you love him or hate him, you can’t deny Lonely Boy lived it up in Season 3. During the ninth episode, Dan hooked up with a famous actor Olivia Burke (played by real-life famous actor Hilary Duff) and Vanessa (Jessica Szhor) at the same time. When Olivia thought she was going to have to leave town to film a big movie, the trio decided to have a threesome. To make things steamier, the scene was set to a sultry cover of the song “Whatever You Like” (sung here by Anya Marina), which is now 100% on my sex playlist.


Nate & Catherine In The Hamptons

Summers get hot anywhere, but there’s nothing like when Manhattanites flock out East. In the Season 2 premiere, Gossip Girl gave a glimpse of a summer in the Hamptons. For some, like Serena, the vacation was quiet and gave her the space she needed to get over Dan (or at least try to). For others, like Nate, the summer was filled with hot sex in secret places with an older, beautiful duchess.


Serena & Nate In Chuck's Kitchen

Who knew something as innocent as toasting waffles could turn into something as hot as kitchen sex? When Serena and Nate finally got together in Season 3, the couple shared the sexiest breakfast ever in Chuck’s kitchen. They casually fed each other caramel, whipped cream, strawberries, and — oddly enough — olives, while getting it on, which is multitasking at its finest.


Blair & Dan In The Elevator

Dan and Blair's attraction seemed simply intellectual at first, and when the two tried to make it more than that in Season 5, neither one of them felt anything at first. After getting drunk and finding themselves in an elevator during Episode 18, however, it seemed they found their groove and got it on in public place after public place.


Chuck & Blair On The Piano

The most tumultuous couple on Gossip Girl had all types of hookups, but few situations were as scorching as their hate sex. After declaring war against each other in Season 4, Episode 7, the exes ripped each other’s clothes off and had passionate sex on top of the piano at Blair’s house in a Pretty Woman-inspired scene that would make Julia Roberts blush.


Serena & Dan On The Jitney

When Serena and Dan, who weren’t together, found themselves riding the jitney in Season 2, Episode 2, the chemistry was palpable. It’s especially apparent when Serena ate chocolate-covered strawberries — which is the strangest bus snack ever — and it got them both in the mood. (I guess because strawberries are an aphrodisiac.) While you don't actually see Serena and Dan having sex, the build-up was hot enough on its own. Besides, what else would they be doing in the bathroom? Talking about their feelings?


Chuck & Blair In Monte Carlo

The CW

Right before these two decided to jump each other's bones for, like, the millionth time during Season 6, Episode 4, Blair told Chuck she was all in on their relationship, and finally, those two got back together and stayed together. I think one of the greatest things about Chuck and Blair is that even when they "hated" each other, they still loved each other — even if it got a little lost in translation

Here’s hoping the reboot offers as much scandalous sex and unrealistic plot points as the original. The new cast has some big shoes — and libidos — to fill.

Both the original Gossip Girl and the reboot series are streaming now on HBO Max.

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