Do you wish Vanessa and Rufus would’ve dated on Gossip Girl? What about Vanessa and Olivia? What about Nate and Lily?

We’ve got 12 relationship combinations that Gossip Girl fans genuinely wished would’ve had the chance to be together on the show.

Stick around to find out about all the potential pairings that viewers missed out on.

Vanessa and Rufus.

Gossip Girl fans have always been obsessed with the idea of seeing Vanessa and Rufus hooking up.

However, truth be told, one of the reasons this relationship pairing is so cringeworthy is that they have such a massive age gap between them.

Another reason is that Vanessa spent a huge bulk of the show attracted to Rufus‘s son, Dan Humphrey. Vanessa and Dan were a couple!

But Rufus pretty much proved that he didn’t mind dating a much younger woman when he started hooking up with Ivy Dickens.

When Rufus did that, it opened up the floodgates of possibility for Gossip Girl fans to start coming to their own conclusions.

Rufus proved that he was down to date younger women, which means he easily could have dated Vanessa!

Rufus and Vanessa always seemed to exchange high levels of sexual tension whenever they were in the same room, so this relationship pairing definitely could have worked.

Vanessa and Olivia.

Wouldn’t it have been intriguing as hell if Vanessa and Olivia explored a romantic connection with each other beyond Dan Humphrey?

They shared a super sexual intimate moment when the three of them participated in a threesome together, but nothing ever blossomed between Vanessa and Olivia after that.

Olivia and Dan were together when they decided to have a threesome with Vanessa, and the results of their threesome were pretty chaotic.

Olivia was edged out of the relationship altogether, and Dan ultimately started dating Vanessa.

While it’s great that Vanessa and Dan had a chance to explore their connection to see if they could truly last in a healthy relationship, it would’ve been far more interesting if viewers got to see Vanessa and Olivia ditch Dan and run off into the sunset together without him.

Chuck and Jenny.

We all know that Jenny swiped her V-card with Chuck Bass on the night he was planning to propose to Blair Waldorf.

Chuck thought Blair had ditched him at the top of the Empire State Building, so he went out of his way to distract himself by sleeping with Jenny.

Beyond the one hookup session between Chuck and Jenny, viewers never got to see if anything real could develop between them.

Chuck and Jenny actually shared a lot in common, including their brooding dispositions, issues with their controlling fathers, and mutual ambition.

They were both hard-working individuals with serious desires to be successful.

Chuck thrived on running the Empire Hotel and Jenny thrived on pursuing a career as a professional fashion designer.

Something real definitely could have bloomed between Chuck and Jenny, but it was never in the cards since Blair was always in the picture as Chuck’s one true love.

Serena and Georgina.

Serena and Georgina’s BFF connection was highlighted on Gossip Girl whenever memories of their party girl days were shown.

One thing we know about Georgina and Serena? Those girls certainly knew how to get down! They knew how to have the time of their lives in just about any setting, scene, or place.

Georgina had a lot of blackmail to hold over Serena‘s head regarding Pete Fairman‘s overdose, but it would have possibly been a little more interesting if they were also harboring some sort of romantic secret between them also.

What if a private little hookup between Georgina and Serena was another secret Georgina was holding over Serena‘s head?

Fans never got to see anything beyond a super toxic frenemy-style connection between Serena and Georgina, but it would have been pretty damn jaw-dropping if there was something more.

Nate and Lily.

Nate dated so many women on Gossip Girl, but two of his girlfriends were more memorable than the others.

That’s because two of his girlfriends were significantly older than he was! We’re referring to Duchess Catherine Beaton and Diana Payne from The Spectator.

Nate clearly had no problem dating women who were twice his age, which leads us to believe that another older woman he could’ve dated is Lily van der Woodsen.

Granted, Lily only ever dated age-appropriate men, but who’s to say she wouldn’t have been down to give someone as handsome as Nate a chance after all the failed relationship she had with men who were her own age.

If anything, it’s guaranteed Lily would’ve been treated with respect by dating Nate since he proved himself to be a good-hearted guy in his character arc throughout the show.

Nate and Penelope.

Penelope had a massive crush on Nate the entire show! She desperately wanted his attention, and she desperately wanted a chance to get to know him.

Nate never seemed interested in Penelope, though.

At first, he was busy dating Blair Waldorf. Then he was busy dating Vanessa Abrams. Then he was busy dating Serena van der Woodson. And on the in betweens, he was giving attention to Jenny Humphrey.

Penelope truly never stood a chance with Nate. But that’s not to say it wouldn’t have been pretty cool to see something unfold between them based on how big of a crush she had on him.

Penelope was always a beautiful girl, but since she was nothing more than a minion to Blair, Nate never took her seriously.

Some fans think he should have since they would have been an aesthetically pleasing pair.

Vanessa and Chuck.

It’s easy enough to understand why so many Gossip Girl fans would’ve loved seeing a real relationship between Vanessa and Chuck.

Viewers saw them briefly hookup with each other without commitment in an episode called Southern Gentlemen Prefer Blondes.

At first, Chuck only pursued Vanessa as part of a twisted bet he agreed to with Blair Waldorf. Later, Chuck and Vanessa kissed each other at a public event to make Blair and Nate jealous.

But imagine if Vanessa and Chuck really had a chance to explore a connection with each other, minus any toxic BS.

The truth of the matter is that Vanessa really brought out Chuck’s good side by helping him grow interested in being a more generous and charitable individual.

That relationship could have been something special.

Blair and Colin.

Blair proved that she was only ever willing to date men of a certain caliber. Just reflect on the majority of her relationship history!

She dated wealthy upper class individuals like Nate Archibald, Marcus Beaton, Prince Louis Grimaldi, and Chuck Bass.

For these reasons, we definitely could’ve seen Blair and professor Colin Forster hitting it off.

Instead, Colin spent his entire time on the show focused on Serena van der Woodson. Colin and Serena were never a good match because he was her professor and she was his student. Their love was forbidden!

If he had chosen to date Blair instead, he wouldn’t have faced any repercussions and he would’ve been able to keep his job as a professor at Columbia since Blair was enrolled at NYU.

Colin fit the standard for being a high value man who could have easily been a good match for a girl in need of princess treatment like Blair. As a reminder, Colin didn’t have a professor’s salary. He was a billionaire who was teaching for funzies.

Damien and Serena.

The way Damien Dalgaard treated Jenny Humphrey in comparison to Serena van der Woodsen should be studied.

There was a night-and-day difference between his treatment of Jenny and his treatment of Serena, but why exactly did that happen?

He was attracted to both blondes, so why did Serena get to see gentleman-style energy from him while Jenny didn’t?

The reason for this is that he thought he’d be properly rewarded for treating Serena well.

Damien knew all about Serena‘s willingness to embrace her sexuality from their days at boarding school together.

That was something he really liked about her. Whereas with Jenny, it was kind of a waste of his time to treat her well since he wasn’t guaranteed any bedroom action with Jenny.

Damien didn’t have patience for Jenny, but he definitely had an eye for Serena since he knew about her party girl reputation.

Another huge reason fans think this relationship could have worked because Serena had the power to turn bad guys good on more than one occasion.

For example, Gabriel Edwards was a con man until he developed real feelings for Serena. Aaron Rose was a playboy who was incapable of settling down until he developed real feelings for Serena. And Carter Baizen was a total scumbag until he developed real feelings for Serena. The same rules could’ve applied with Damien.

Louis and Georgina.

Prince Louis wanted loyalty from his partner, but that’s not something he was able to achieve in his relationship with Blair Waldorf.

Georgina Sparks wanted a steady relationship with a wealthy man who could take care of her financially.

For these reasons, fans agree that Louis and Georgina easily could have been a great match.

Viewers can picture Louis being attracted to Georgina since he was attracted to Blair, who also happened to be a pale-skinned brunette with a pretty face and an ambitious go-getter mentality.

Fans can also picture Georgina being attracted to Louis since the men she dated along the way in Gossip Girl were always extremely well-off and successful.

Since Louis was a full-fledged prince, we have no doubt Georgina would have jumped on the opportunity to be with him if she could have.

Jenny and Carter.

The major reason why tons of Gossip Girl fans can picture a relationship blooming between Jenny and Carter is that Jenny was clearly attracted to guys who didn’t exactly have her best interest at heart.

Her relationships with Asher Hornsby and Damien Dalgaard serve as proof of that. In true Jenny Humphrey fashion, it would’ve made sense for her to hop into another toxic relationship with someone like Carter if the writers of the show had given them the opportunity to connect.

And keep in mind that Carter proved he could present himself in different ways based on the girls he was spending time with.

For example, he was down for having sex with no strings attached when he was with Blair Waldorf, but he pursued a serious committed relationship with Serena van der Woodsen.

What if he attempted to pursue any variation of a romantic connection with Jenny? This is a question fans of the show are still asking to this day.

Chuck and Lola.

While most Gossip Girl fans are fully aware that Chuck was always destined to end up as Blair Waldorf’s husband, there could have been room for exploration with other young women along the way.

When Lola Rhodes surface, she briefly dated Nate Archibald, but what if she had the opportunity to date Chuck as well?

The reason some fans of the show think this relationship could’ve worked is that Chuck clearly had somewhat of an attraction to blondes after seeing that he try to hookup with Serena van der Woodsen in Episode One, he swiped Jenny Humphrey’s V-card, and he fell in love with a blonde woman in France named Eva Coupeau.

On top of that, Chuck and Nate already had the experience of falling in love with the same woman. Who could forget about the time they both had feelings for Raina Thorpe? Seeing Chuck try things out with Lola could have been interesting.

Which of these relationship pairings on Gossip Girl do you wish you could have seen on the show? Let us know your thoughts in the comment section below.