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.
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.
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!
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).
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.
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.
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!