The Best—And Worst— Gossip Girl Couples of All Time

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I still have a soft spot for Gossip Girl, despite its many ridiculous plot lines and even more ridiculous ending. (You know, when that guy was revealed as the titular G.G.) But for all its faults, the CW show delivered the goods, particularly when it came to love. Gossip Girl gave us so many couples throughout its six seasons—some good, some bad, some very, very confusing.

Here's our condensed list of Gossip Girl's most important couples: the ones that worked, and the ones that should have been banned from Manhattan.

Best

Serena and Nate

I'll say it: I wish these two had rekindled their flame. Dubbed the Golden Couple by Gossip Girl herself, the luscious locks between the two were reason enough for them to get back together. They made the prettiest couple. So! Pretty!

<h1 class="title">GOSSIP GIRL, Blake Lively, Chance Crawford, 'Hi, Society', (Season 1, aired Dec. 5, 2007), 2007-. ph</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, Blake Lively, Chance Crawford, 'Hi, Society', (Season 1, aired Dec. 5, 2007), 2007-. ph

©CW Network/Courtesy Everett Collection

Chuck and Blair

When the show was on, I had no problem saying those three words, eight letters to these two: I love you. Ed Westwick and Leighton Meester had so much chemistry on G.G. that my TV screen melted a little each time they were on it. Could a normal relationship withstand an attempt to sell the girlfriend for a hotel, a pregnancy and marriage to another (royal) guy, a near-death car accident, approximately 8 million breakups, and 9 billion revenge hookups? No. But the love between the bespoke-purple-suited Chuck and crowned-by-headband Blair was not for mere mortals.

My feelings about Chuck are more complicated now, considering, in 2017, Westwick faced sexual assault charges. (He wasn't prosecuted due to insufficient evidence, per NBC News.) But for our story here, we'll focus on the fictional characters and not the men or women who play them.

<h1 class="title">GOSSIP GIRL, from left: Leighton Meester, Ed Westwick, 'There Might be Blood', (Season 2, ep. 209, a</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, from left: Leighton Meester, Ed Westwick, 'There Might be Blood', (Season 2, ep. 209, a

©CW Network/Courtesy Everett Collection

Rufus and Lily

How did a couple that made no sense at all make so much sense? She's Upper East Side; he's Brooklyn. Her fashion is impeccable; he wears the same flannel shirt four times a week. They have a secret love child that neither of them seem to care about, and she left him at one point for Bart Bass. Yet Rufus and Lily always endured. I forever stan.

<h1 class="title">GOSSIP GIRL, from left: Kelly Rutherford, Matthew Settle, Lee Ranaldo, Mark Ibold, Kim Gordon, Thurs</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, from left: Kelly Rutherford, Matthew Settle, Lee Ranaldo, Mark Ibold, Kim Gordon, Thurs

©CW Network/Courtesy Everett Collection

Eric and Jonathan

Seriously, why did Eric disappear? He and cutie boyfriend Jonathan were probably the least drama-prone couple ever on the show, until Jenny had to go and ruin it. Jenny ruins everything, including but not limited to: fashion shows, my opinion on eyeliner, and young love.

<cite class="credit">The CW</cite>
The CW

Eleanor Waldorf and Cyrus Rose

Two words: Wallace. Shawn.

<h1 class="title">GOSSIP GIRL, from left: Wallace Shawn, Margaret Colin, 'O Brother, Where Bart Thou?', (Season 2, ep.</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, from left: Wallace Shawn, Margaret Colin, 'O Brother, Where Bart Thou?', (Season 2, ep.

©CW Network/Courtesy Everett Collection

Dorota and Blair

While a platonic couple, yes, no one loved each other more on G.G. than Blair and Dorota. While Vanyas and Chucks may come and go, these two are family forever.

<h1 class="title">GOSSIP GIRL, from left: Zuzanna Szadkowsk, Leighton Meester, 'Remains of the J', (Season 2, ep. 220,</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, from left: Zuzanna Szadkowsk, Leighton Meester, 'Remains of the J', (Season 2, ep. 220,

©CW Network/Courtesy Everett Collection

Worst

Blair and Dan

Yes, they're the two smartest members of the crew who share pretentious tastes in literature and old movies and love-hate feelings toward Serena. But I'm sorry…gross. No. I felt sick when they kissed. Blair could maybe get past his Brooklyn upbringing, but the most polished woman alive would never truly fall for someone with such messy style.

<h1 class="title">GOSSIP GIRL, (from left): Leighton Meester, Penn Badgley, 'Damian Darko', (Season 4, ep. 413, aired</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, (from left): Leighton Meester, Penn Badgley, 'Damian Darko', (Season 4, ep. 413, aired

©CW Network/Courtesy Everett Collection

Blair and Louis

Blair Waldorf is royalty in her own mind; she didn't need Prince Whoever, his devious family (she has her own), or his dowry blackmail nonsense.

<h1 class="title">GOSSIP GIRL, l-r: Hugo Becker, Leighton Meester in 'All The Pretty Sources' (Season 5, Episode 8, ai</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, l-r: Hugo Becker, Leighton Meester in 'All The Pretty Sources' (Season 5, Episode 8, ai

©CW Network/Courtesy Everett Collection

Serena and Dan

I might get a lot of disagreement here, but I hated these two. Rufus is the only Humphrey man who can handle being an Upper East Side house-husband. The giant chip on Dan's shoulder kept getting in the way of his relationship with Serena. I know these two were a real-life couple once, but the second Blake Lively married Ryan Reynolds, her scenes with Penn Badgley lost their excitement.

<h1 class="title">GOSSIP GIRL, Penn Badgley, Blake Lively, 'Dare Devil', (Season 1, aired September 26, 2007), 2007-,.</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, Penn Badgley, Blake Lively, 'Dare Devil', (Season 1, aired September 26, 2007), 2007-,.

©CW Network/Courtesy Everett Collection

Jenny and Chuck

Remember how Chuck attempted to sexually assault Jenny in the first season, and then later she ended up losing her virginity to him willingly? Yeah, NO.

<h1 class="title">GOSSIP GIRL, from left: Taylor Momsen, Ed Westwick, 'Dan de Fleurette', (Season 3, ep. 304, aired Oc</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, from left: Taylor Momsen, Ed Westwick, 'Dan de Fleurette', (Season 3, ep. 304, aired Oc

©CW Network/Courtesy Everett Collection

Georgina and Dan

Too much scheming and lies in one “relationship,” if you can even call what they had that.

<h1 class="title">GOSSIP GIRL, Penn Badgley, Michelle Trachtenberg, 'Women on The Verge', (Season 1, aired May 12, 200</h1><cite class="credit">PATRICK HARBRON/The CW</cite>

GOSSIP GIRL, Penn Badgley, Michelle Trachtenberg, 'Women on The Verge', (Season 1, aired May 12, 200

PATRICK HARBRON/The CW

Vanessa and anyone

She tried with Nate, she tried with Dan (and briefly, with Dan and Hilary Duff), she tried with Dan's secret half-brother, and I think she even hooked up with Chuck. But no. The writers could just never seem to make Vanessa's relationships work, which is disappointing.

<h1 class="title">GOSSIP GIRL, Penn Badgley, Jessica Szohr, 'School Lies', (Season 1, ep. 112, aired Jan. 2, 2008), 20</h1><cite class="credit">©CW Network/Courtesy Everett Collection</cite>

GOSSIP GIRL, Penn Badgley, Jessica Szohr, 'School Lies', (Season 1, ep. 112, aired Jan. 2, 2008), 20

©CW Network/Courtesy Everett Collection

Rufus and Ivy

Shudder. Let's never speak of this again.

<cite class="credit">The CW</cite>
The CW
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