In the world of teen dramas, nothing stirs more flames of the fandom fire more than the dawning of a new relationship, and Gossip Girl is no exception. Over the last year, there has been little talk outside of Blair and her many suitors, but we’re beginning to think that it is getting a little boring. There are so many untapped potential relationships that it’s time we highlight some these possible story line gems and give voice to some unique pairings.

5. Dan/Alessandra

Over the first half of season five, our favorite Brooklyn hipster has had everything but the kitchen sink thrown at him, but there has be one constant in his life – Alessandra, his book agent. She is everything Dan looks for in a woman — clever, passionate, feisty, and following with more recent desires, brunette. She has no illusions about his circle of friends, and is willing to call it as she sees it (To Chuck: “All I could think was how long you must have been hanging there before anybody found you.” To Dan: “And don’t shave. It makes you look like a real writer”). When Dan starts acting like a Prima Donna, refusing to attend book signings and publicity events, in an act of extreme-meta, she took to Twitter and started hating on him anonymously to motivate him and bruise his inflated ego a bit. A Dalessandra hookup would inject some fun into the season, and on a show that claims to be scandalous, Dan’s body has been ready (and unused), for a very long time.

4. Lily/Nate

This one seems so obvious, that it is surprising the writers have yet to go there. If there are two things we have learned on Gossip Girl, it’s that Nate likes older women, and unless Lily is doing something nefarious, she is pretty useless. Nate could give Lily that thrill of youth that she has been missing since Rufus became lame, and assist her in her favorite past-time-ruining Serena’s life. Not only is Lily a cougar, she is also self-absorbed, spiteful, and scheming, she is the exactly what he looks for. In “Memoirs of an Invisible Dan”, we saw how excited Lily got when reading about Nate’s fictionalized romantic adventures, and I have a feeling Lily would have no qualms with dressing like Julie Andrews and acting out Nate’s favorite movie. Imagine the drama that would unfold when Serena and Rufus discover the sordid affair. Serena will pretend to care about Nate for at least one episode, and Rufus will refuse to make waffles for an entire week!

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3. Nate/Penelope

It’s a story as old as time, or at least as old as teen dramas and rom-coms. Poor Penelope has been in love with Nate forever, but he never notices her undying devotion. There is even plenty of set-up this season to further this story. Penelope, angry that she hadn’t been invited to Georgina’s scheme against Chuck, makes her way over to bar herself and sees Nate, depressed about his Grandfather’s lack of faith in him, sitting alone, whiskey glass in hand. Full of liquid courage, she walks over to him and begins to talk. During the conversation, he realizes that maybe someone does see the real him, and he slowly begins to fall for her. It will be a sweeping romance that would have us laughing, crying, and cheering. It will come to a shocking end when Nate accidentally stumbles upon a half-dressed Lily (see above).

2. Chuck/Ivy

Beautiful, intelligent and sneaky, Ivy would be a great match for Chuck. She wants money, he has it in spades. He wants a family, and Ivy’s main reason for continuing her Rhodes-ruse is because she wants family; they could be each other’s family. They would scheme against their enemies together, and the moment he tried to shift the balance in the relationship, she would smack him down like a gnat. Three words, eight letters? Psh, no need for any of that romance nonsense, she will constantly be trying to steal all his monies, and he will be in awe of her masterful manipulations. Okay, so they haven’t actually interacted, but we still have a season and a half (most likely at least) for these two create fireworks. Best thing about Chivy? He would definitely call her Serena.

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1. Vanessa/Rufus

Vanessa and Rufus. Rufus and Vanessa. Has there been any two characters that had more accidental chemistry than these two? Anytime they shared a scene together, their eyesex bordered on inappropriate; the sexual tension in most scenes was almost palpable. The reason no one could ever buy into the Dan/Vanessa story line was because she was obviously just using the younger Humphrey as a substitute for her true object of desire. Let’s not forget that she also dated Rufus’s other son, Scott. Rufus is clearly Vanessa’s soulmate, and she is perfect for him too. She loves waffles, pierogies, and judging people from her hypocritical, morality high-horse. Unlike Lily, Vanessa would at least pretend to care about what Rufus has to say, and he would always eat her tofu stuffing. Of course, since Vanessa is no longer on the show, this is one pairing that will most definitely never happen, but the dedicated Vufus shipper-base will forever continue hoping that these two will finally get the chance that they deserve.

Honorable Mentions:




What’s your favorite non-canon/crazy Gossip Girl ship? How would you like the writers to implement their story? Would you be satisfied with a one night stand or are you looking for endgame material? Let us know below!

I am a ridiculous, mess of a person, who spends far too much time thinking and writing about fictional characters and their relationships. I watch massive amounts of television as a substitute for human interaction, because let's face it, it's a lot more fun to pretend that Nate Archibald and Rory Williams are your bffs than to go outdoors and deal with real people.
  • Andy

    Chuck and Ivy for endgame!!

  • Dan and Alessandra
    And Chuck and Ivy never happen

  • Dan and Ivy

    • I actually like Dan and Ivy together, mostly because he’s not worthy of the other two girls in my eyes, lol. But they ARE canon, so no worries there. 😉

  • Ivy and Dan forever

  • Dan and Alessandra
    and Dan and Ivy

  • Penelope and Nate
    Dan and Ivy

  • I want Ivy and Dan

  • Dan and Ivy
    Ivy and Dan

  • Chuck and Blair
    Dan and Ivy

  • Dan and Ivy for endgame!!

  • Amy

    Charlie or Ivy and Dan

  • Dan and Ivy /Divy
    Nate and Penelope

  • Ivy and Dan
    Lily and Nate

  • Chuck and Blair
    Dan and Ivy
    Serena and Nate

  • Dan and Ivy

  • Karlos

    Chuck and Ivy? WTF. NO. NO. NO. K?

  • this post was hilarious, lol! go Dalesandra! and I like Louis/Georgina too. they’ve never met but look at their potential! after Blair and Louis break up, Louis would be hurt and ready to scheme. and who loves to scheme even more than Blair and Chuck? Georgie! they would be awesome! hahaha

  • Violet

    This is just stupid…..

    I remember when this site was fun and didn’t try too hard.

  • lana

    Chuck and Georgina! She took his virginity and you know he’d love it. They’re the biggest schemers and backstabbers in the show, not to mention both being batshit crazy. Match made in heaven!

  • Goober

    Dan/Blair, Nate/Penelope and Chuck/Monkey FTW!

  • i agree with all of this!!

  • Guest

    Chuck/Ivy/monies for endgame!

  • Eugenia Polegri

    Hahaha! Loved it!<3

  • LE

    VANESSA AND RUFUS!!! Lol. They just had all sorts of chemistry, and I can’t imagine a bigger scandal on GG than Rufus cheating on Lily with his son’s ex-gf (though I do love me some Rufly, what’s gossip girl without some ruffled feathers? 😉 :P)

    • Guyzrhot123

      totally AGREE!!

  • Elizabeth

    Love that Chuck/Ivy made your list – yes!

    Also, how about Blair/Jack?

  • Alessa

    Dorota and Chuck 😀

  • I want to see Diana/Jack. I know that would be an evil duo of doom, taking evrrybody down.

  • Neiro

    Dan/CeCe all the way!

  • Ella

    Ooh… Dan and Cece.. I wanted to see how they go coz I think they sort of have a thing for each other but just a little :))))))))))))))

  • Celine

    I can see the rest but not Chuck and Ivy, though Nate with Lily sounds pretty awful too

  • LonelyBoyLover


  • Cherry195

    jenny and chuck
    nate and serena
    blair and dan
    vanessa and scott

  • isabella

    Dan and Alessandra. The rest are pretty gross and the only reason I would want Dan to be with Alessandra is so he can get the f away from Blair.

  • Jenny