TheTalko.com

We Ranked The 20 Least To Most Romantic Moments From 'Gossip Girl'

Hey there, Upper-Eastsiders. Sadly, it’s not Gossip Girl here. But even though it’s been nearly six years since the final episode aired, we’re still as obsessed with the secret lives of Manhattan’s elite now as we were back then. Though they were still in school when we met them, Serena van der Woodsen, Blair Waldorf, Chuck Bass, Dan Humphrey, and Nate Archibald had an everlasting effect on our lives. This gang showed us what life is like with a trust fund and servants, but they also taught us that it only takes a minute to lose it all—and all that glitters might just be a cheap gold-plated knock-off version of true happiness.

The skeletons pouring out of the closets of these privileged characters certainly drew us into their world, but let’s admit it: we stayed for the true romance. There were many pairings over the seasons, from those who were destined to be together forever to those who had such little chemistry that their time together on-screen is still painful to watch.

From the thrilling moments of Chair to the comparatively tame scenes shared by Serena and Dan, we ranked the top couple moments of Gossip Girl history, from least to most romantic. Check them out below!

advertising

20 Least Romantic: Nate And Serena Have A Super Cute Water Fight

youtube.com

If you ask us, Nate and Serena made one of the best couples on the show. There was an undeniable attraction between them from the get-go (so much so that they were both willing to betray someone they cared about to give in to their urges), and they always cared for each other, even after hurting each other over and over again.

Their water fight is one of our favorite moments (though sadly still comes in as the least romantic of the truly romantic scenes).

Nate tries to help Serena sober up, but they both end up wet and laughing their heads off.

19 Dan And Vanessa Finally Move Out Of The Friend Zone

youtube.com
advertising

There was a mixed reception to Vanessa Abrams, Dan’s BFF. Some viewers found her to be a welcome breath of fresh air from the other snobby elitist characters, while others thought that she simply complicated Dan’s life for the worse.

Either way, it was exciting when she and Dan finally gave into those deep feelings and made the (temporary) transition from friends to lovers. Their relationship was super confusing and had a lot of low moments, but despite that, these two did truly care for each other, and it felt good to see them explore that. Or, you know, get it out of their system at least.

18 Chuck Steps In For Blair’s Perfect Birthday Present, Not Nate

pinterest.com

Fair warning: we’re firmly team Chair, so there are a lot of Chuck and Blair moments on this list. Though Chuck Bass didn’t start out as a sympathetic character, he went through an extreme amount of growth, did a total turn around, and proved himself again and again to be the perfect gentleman.

The next romantic moment on our list is when Chuck made sure that Blair received the necklace she put on hold for her birthday.

As Nate and Blair were getting closer to being back together at the time, it was really Nate’s job to do that, which just shows how deeply Chuck cared for Blair.

17 Serena Agrees To Go Out With Dan For The First Time, Marking The Beginning Of Their Complex Relationship

fanpop.com
advertising

The relationship between Serena and Dan was the central point of interest for many fans of the show. So of course, the moment where Serena agreed to go out with Lonely Boy for the first time was a huge deal, and had to make the top 20! This kicked off their whole dating life and was responsible for all the craziness that followed.

The context is pretty romantic: Dan has a huge crush on this blonde beauty from school, but she doesn’t even know that he exists. On a whim, he gets the courage to ask her out, and she agrees because he can’t be worse than the guys she does know. Magic.

16 Blair Supports Chuck At Bart’s Funeral Like Only A Real Friend Could

woodycakes.livejournal.com

You could argue that at times, Chuck and Blair’s relationship became a little bit toxic. They hurt each other and they hurt other people, and nearly decided to call it quits for good because of that.

But there were also times where you could see that these two just had each other’s backs.

Yes, they had diamonds and roleplays and every thrill you could imagine, but their relationship was born out of true love and affection. Take Bart Bass’s funeral. Chuck is clearly a mess, but Blair is there for him, alongside Nate, making sure he doesn’t fall apart. That’s real romance.

15 The Tension Between Blair And Dan Boils Over Into A Long-Awaited But Still Weird Kiss

hollywoodife.com
advertising

Some fans aren’t going to be happy with us for even mentioning Dair, or that strange period where Blair and Dan put aside their disdain for each other and ended up briefly having a thing. But regardless of the consequences of their short relationship, and the fact that it could have jeopardized their relationships with Chuck and Serena, you have to admit that their first kiss was a pretty romantic moment.

It’s always exciting when two people who used to hate each other realize they have chemistry. The tension of it all was almost too much! But we are glad that these two quickly found that they were better off as friends.

14 Blair's Dream Comes True When She Meets A Prince In A Parisian Museum

xoxogossipgirl.wikia

To find this moment romantic, you have to forget what you know about Prince Louis of Monaco. In hindsight, Blair’s decision to marry Louis was ill-advised. He was a power-hungry monster who cared more for his reputation than Blair’s feelings. But when they met in an idyllic museum in Paris, we didn’t know any of that.

So in its isolation, Blair actually meeting a real prince and speaking to him in French in Paris surrounded by romantic art pieces was pretty spectacular.

This is the kind of thing all girls have dreamed about at least once, whether they care to admit it or not.

advertising

13 Dan Buys Serena A Low-Key Dinner To Cheer Her Up, Proving He's Still Her White Knight

allthatcubeness.wordpress.com
advertising

Derena, or Dan and Serena, also had their fair share of toxic moments that made us wish they would leave each other alone for good. But they also shared some cute scenes that reminded us of why they fell in love in the first place. Though their worlds were crazy, they just seemed to know each other better than everyone else knew them. They shared an unspoken bond and knew how to cheer each other up.

Part of us thinks that they would have made better friends than lovers, and Serena should have ended up with Nate, but the scene where Dan buys Serena comfort food she loves in a diner really warmed our hearts.

12 Lily Finally Takes The Plunge And Becomes A Humphrey

latimesblogs.latimes.com

Now, here’s a couple we were rooting for! Lily and Rufus had history and an even stronger bond than their kids, Serena and Dan, had. So to see them finally allow themselves to be together despite all the confusion surrounding them was amazing, and that’s why their low-key but classy wedding has made this list.

We know that Lily and Rufus being together made it weird for Serena and Dan to be together, but if we had to choose, we would be team Lily and Rufus any day!

Sadly, they didn’t last, but we are glad they both found their happy endings.

11 Chuck's Heart Breaks As He Watches Blair Have Her Fairytale Wedding

vulture.com
advertising

Everyone loves a royal wedding, right? It mustn’t be that great if you have to watch the person you love marry the prince or princess of their dreams. Sure, Louis turned out to be Blair’s nightmare, but at the time, Chuck just thought he was watching the love of his life being swept away by someone from a fairy tale.

This was a sad moment for Chuck and Blair fans, but it was still romantic because it highlighted just how unbreakable the connection between these two was. It was one of those painful scenes that you couldn’t tear your eyes away from.

10 Dan Shows Serena He's Not Like All Her Other Boyfriends By Taking Her On A Vespa

wetpaint.com

The girls of Gossip Girl were treated to some pretty out-of-this-world dates that made the rest of us feel pretty crummy about our own love lives. It was nothing out of the norm for them to be whisked away on private jets or treated to diamonds. But every now and then, it was a welcomed surprise to see them living a little more normally.

On Dan and Serena’s first date, he organized a limo to try and impress her, even though she assumed he’d take her on a scooter.

Then in Season Six, when they started to come back together, he finally came through with that Vespa. The perfect date!

9 Chuck Makes Blair’s Prom Dreams Come True, Though He Gets Nothing Out Of It

pinterest.com
advertising

We all dreamed of the perfect prom experience, but the majority of us probably didn’t have quite as good a time as Blair did. Even though Nate was her partner, Chuck was the one behind the scenes making the magic happen, as per usual. It seemed like he was actually sabotaging her prom dreams, but he was really orchestrating everything so that she would have the perfect prom. That included voting for her 150 times so she could be prom queen like she’d always wanted.

This was more evidence that Chuck was Blair’s true love, and almost like her guardian angel (an angel wearing devil’s horns, but still).

8 Nate Tries To Save Serena, His Secret True Love, From Tripp

xoxogossipgirl.wikia

We don’t want to harp on about what a great couple Nate and Serena made, but we will. They each understood the other’s problems, had many very similar experiences, and were pretty much attracted to each other since the beginning.

They were essentially made of the same stuff, not to mention the fact that they looked great together.

Though they didn’t end up together, Nate still proved that he cared about Serena. When she became involved with Tripp, Nate begged her to choose him instead. But being Serena, of course, she chose the complicated, painful path and went with Tripp.

7 Chuck And Blair Get Properly Acquainted In The Limo

gone-withthe-wind.blogspot
advertising

Okay, this moment was a little too risque to include a picture of, but it stuck in our brains the first time we saw it anyway. We can still imagine it quite vividly! After having some fun at Chuck’s burlesque club, Victrola, the two schoolmates hop in his limo. And the rest is truly history.

his was such an important moment because it marked the beginning of the super complicated love affair between Chuck and Blair, which would go on to pretty much dominate both their lives for the rest of the show. Not that they (or we) were complaining.

6 Eleanor Marries Cyrus In White

popsugar.com

Cyrus Rose had to be one of our favorite characters on the show. Intelligent and caring, he was the perfect partner for a strong woman like Eleanor Waldorf. He’s also the one to officially marry Chuck and Blair, so as far as we’re concerned, he’s an icon. Blair wasn’t his biggest fan at first, but that’s just Blair. He eventually improves her life for the better.

Naturally, the impromptu wedding between Cyrus and Eleanor just melted our hearts.

Most of all, this was such a romantic moment because we knew that this couple was truly meant to be together.

5 Blair And Chuck Lose Their Egos At Eleanor And Cyrus’s Wedding

fanpop.com
advertising

Eleanor and Cyrus’s wedding may have been a beautiful occasion, but it also took place right around the time that Bart Bass passed away (or so we all thought). Chuck wasn’t at his best at this point and wasn’t able to be his usual cool and collected self at the ceremony. Instead, Blair found him upstairs on the bed, grieving his dad.

This was such a sad and touching moment because she immediately went over to him and hugged him, showing him that she felt his pain and would be there for him, no matter how tough things got. We’re not crying. You’re crying.

4 Derena Tie The Knot On the Upper East Side

pinterest.com

The wedding between Serena and Dan was something fans were waiting for since the pilot episode, so of course, it ranks pretty high up on our list.

Set in the not-too-distant future, Dan and Serena tie the knot where their journey first started, in Manhattan.

Serena’s iconic gilded dress pretty much makes this scene, along with the reappearance of old faces like Little J and Serena’s brother Eric. In many ways, Dan was a bit of a jerk by the end of the series, particularly after the truth about Gossip Girl’s identity was revealed. If it weren’t for that, this might have been the top moment.

3 Blair, In Oscar De La Renta, Begs Chuck Not To Leave

halfchocolate.com
advertising

Only Blair could pull off Oscar de la Renta at a Parisian train station and not look over the top. In this heartbreaking scene, where Chuck has finally grown out of his childish ways and become an honest, earnest man, Blair begs him not to run away. This was also super emotional because it was their first reunion after Chuck’s accident.

Plus, it contained some of the best dialogue we’ve seen from these two. “Your world would be easier if I didn’t come back,” Chuck tells her. “That’s true,” she replies. “But it wouldn’t be my world without you in it.”

2 Chuck And Blair Get Hitched In Central Park

wetapint.com

Really, there was no better way to close the Chuck and Blair story than to have them get hitched in Central Park. This was something we’d all been waiting for, and to finally see it was magical. After Blair’s huge royal wedding, we’re glad that they decided to keep this one part of their lives small, close and intimate.

The dress and the ceremony were both perfection and the best thing is that, as far as we know, Chuck and Blair’s marriage was a success.

In the final snapshot into the future, we saw that they even had a son named Henry. Bless!

1 Most Romantic: Three Words, Eight Letters, He Said It

hellogiggles.com
advertising

And we’ve come to our top romantic moment. At the white party in Season Two, Blair delivered this monumental line to Chuck, even though he wasn’t her date: “Three words, eight letters. Say them and I’m yours.” At the time, Chuck broke all of our hearts by not being able to get them out.

But eventually, Chuck was able to utter those three words that meant so much to Blair and transform their relationship from being a cat-and-mouse game to true love. This was a moment Chair fans had prayed for, and it couldn’t have been pulled off in a better way.

references: metro.co.uk, nkdmag.com, ibtimes.com, buzzfeed.com, elitedaily.com

advertising
Give TheTalko a Thumbs up!

More in Entertainment