Daily Life

The best and worst couples in the history of Gossip Girl

From too hot to handle to downright weird, here’s our ranking of the show’s iconic hook-ups.

By Josie Rozenberg-Clarke
It’s been 10 years since the ultra-glam series Gossip Girl first graced our screens.
The show introduced us to a group of ridiculously good-looking young people as they bitched, schemed and slept their way around New York City. Teen angst has never looked quite so good!
To celebrate the show’s birthday, we sifted through the many hook-ups and break-ups to compile this definitive list of couples, from worst to best.
You know you love them…

10. Chuck & Jenny

The weirdest pairing has to be these two. It all started in Season 1 when Chuck (Ed Westwick) tried to rape 16-year-old Jenny (Taylor Momsen) at a party.
You think she’d avoid him like the plague after that, but in Season 3, Jenny decided to lose her virginity to Chuck, which caused Blair (Leighton Meester) to break up with him.
Thankfully “Chenny” learned their lesson and never touched each other again.

9. Dan & Vanessa

Sorry, we fell asleep just reading their names!
Dan (Penn Badgley) and Vanessa (Jessica Szohr) had the potential to be cute – two long-time friends finally admitting their true feelings for each other, aww! – but because they’re both beiger than beige, the hook-up fell flat.

8. Rufus & Lily

Dan’s dad and Serena’s (Blake Lively) mum could have been amazing together, but their marriage didn’t last.
Theirs is the classic tale of two lovers from different worlds, but like Romeo and Juliet, there was no happy ending for working-class Rufus (Matthew Settle) and high-uptown girl Lily (Kelly Rutherford).

7. Dan & Serena

Okay, we would have been here for this marriage if it hadn’t been revealed that Dan was actually Gossip Girl all along, writing nasty stories about everyone on his anonymous poison pen blog for years.
Why would Serena marry someone who had been dragging her name through the mud with slanderous gossip ever since they met? We would have taken out an AVO instead…

6. Dan & Olivia

This only makes the list because we love Hilary Duff, and when her character Olivia – a Hollywood star trying to lead a “normal college life” – had a threesome with Dan and Vanessa, it was one of the show’s most ridiculous and awesome plotlines.
We wish Olivia had stayed in our lives forever.

5. Nate & Catherine

It’s massively creepy because Catherine (Madchen Amick) was old enough to be Nate’s (Chace Crawford) mum, but their secret tryst in the car is one of the hottest moments of Gossip Girl.
So they’ve gotta get points for that.

4. Dan & Blair

This hook-up is a controversial one as it seemed a little out of character for both of them.
Upper East Sider Blair slumming it with Brooklyn boy Dan? As if!
Maybe the writers were running out of people to put together, so in Season 4, after their friendship had blossomed, the former enemies share a kiss and some major feelings develop.
But self-sabotaging Dan went crazy and killed any chance of romance. They could have had it all!

3. Nate & Serena

Nate is the king of the steamy hook-up! His clothes-ripping encounter with Serena is the scandal that kicked off the series – because he was dating her bestie Blair at the time.
In Season 3 the photogenic couple reunited but the union fizzled. Too pretty to function, perhaps?

2. Cyrus & Eleanor

These two are couple goals! Blair probably should have looked at her mum Eleanor’s (Margaret Colin) adorable relationship with Cyrus (Wallace Shawn) as a guide for her own personal life.
Cy treated Eleanor like a princess – kind of like Chuck without the creepy possessiveness

1. Chuck & Blair

Yes we did just use the word creepy to describe them, but there’s no denying that, for better or worse, “Chair” are the most iconic couple of the entire series.
Their on-off, love-hate relationship was the only constant within the show.
They had more passion in their little fingers than the rest of the couples combined. And for that, they are our King and Queen forever!

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