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Gossip Girl Valentine's Day Wishes: Which Upper East Siders Belong Together? - Featured

It's almost Valentine's Day and no matter if you're missing your sweetie or making romantic plans with him or her, there's definitely something all us CW fanatics are seriously missing: Gossip Girl!

So, while we continue to await GG's March return, let's do a little Vday love matching. Gossip Girl is one of the most intertwined, confusing, and sometimes almost incestuous, show when it comes to our favorite characters' love lives, so we want to know who of all the love pairings for the main characters you think they are meant to be with.

For example, I used to be a big fan of Serena and Dan, but now in Season 3, I can't possibly imagine them together ever again! As a true-blue Chuck and Blair fan, I cringe at the rumors of their impending break up!

So how about you? Who of these pairing below (or other unmentioned matches) do you think belong together?

Chuck & Blair

Nate & Blair

Nate & Serena

Nate & Vanessa

Nate & Jenny

Dan & Serena

Dan & Vanessa

Dan & Georgina

Here's hoping all our Gossip Girl Valentine's Day wishes come true!


| Mar 5, 2010 11:09AM EST
Chuck & Blair <3 <3 <3Dan & Vanessaand DEFINITELY NATE & SERENA <3 :D
| Feb 22, 2010 6:38AM EST
chuck and blair the other characters don't matter
| Feb 17, 2010 8:16PM EST
Chuck & Blair FOREVER!!!!!!! <3 <3 <3 Dan & Serena <3 <3
| Feb 17, 2010 6:21PM EST
Nate and Serena!Everyone else can do whatever they want.
| Feb 17, 2010 11:16AM EST
Chuck and Blair
| Feb 17, 2010 6:38AM EST
Chuck and Blair!Serena and Dan back together.and about the othery, maybe someone new? but i really hope it's not gonna be serena and nate...don't like it.
| Feb 16, 2010 8:44PM EST
Why is everybody hating on Vanessa? She's great and not to forget; gorgeous!Altough I don't have any idea what could make her more interesting for the overall storyline. I have to agree she's a bit boring and Dan + Vanessa would make a boring couple too. love Chuck & Blair, definitely. But I think it's time for a little shake up. I would be sad if they break up though. And somehow I don't really like Serena + Nate. Maybe some new blood in the series? And I hope Jenny won't turn out as a junky.
| Feb 16, 2010 5:28PM EST
Dan & SerenaNate & JennyChuck & BlairFav couple are Nate & Jenny though
| Feb 16, 2010 11:47AM EST
Nate & Jenny Chuck & Blair
| Feb 16, 2010 11:08AM EST
Obviously Chuck & Blair forever
| Feb 16, 2010 8:09AM EST
Chuck and Blair, the perfect couple :D
| Feb 16, 2010 4:08AM EST
Chuck and Blair!! Nate and Serena, Dan and Vanessa
| Feb 15, 2010 2:55PM EST
Chuck & Blair---- can't imagine it any other way Nate & Jenny----- honestly, since season one these two have got more chemistry than nate and blair or nate and serena Dan & Serena---- they were cute together but knowing what we know now... don't know how that would work Vanessa & Chuck---- just in case chuck and blair should break up, then chuck and vanessa can take a stab at it... afterall it's not like they havent 'done it' before... But I really hope they bring on a love interest for Nate... a storeyline that people actually cares about (well i know i dont care about his family and their problems).
| Feb 15, 2010 11:16AM EST
I only actually believe in Chair now cause Chuck & Blair are just soo amazing together 8 words 3 letters! Serena & Jenny & Vanessa are all whores i just can't stand them anymore they're soo annoying. I think Nate needs some loving cause everyone keeps messing him around its so sad.Dan's an idiot though he really shouldn't get together with Vanessa. Although can't wait to see Jenny get together with Kevin Zegers character :)
| Feb 15, 2010 8:28AM EST
Blaire & Chuck for sure, they're meant for each other. I use to like Serena & Dan but they've ruined that one for me. xD So I'd like to see Nate with Serena. Dan with Vanessa or bring Hillary Duff back. Jenny is so irritating, I'd like to see her get pushed off a building. (=
| Feb 15, 2010 7:39AM EST
Chuck & BlairNate & Jenny
| Feb 15, 2010 7:28AM EST
Easy: Chuck and Blair ♥♥Nate and Jenny ♥Dan and SerenaGeorgina and Damien (drug dealer guy)Vanessa - deserves to be alone, she's so annoying! :):)
| Feb 14, 2010 5:47PM EST
Chuck & BlairDan & SerenaNate & Vanessa
| Feb 14, 2010 2:42PM EST
Chuck and BlairSerena and NateSerena and DanNate and JennyVanessa and Dan (MAYBE...)
| Feb 12, 2010 8:20PM EST
chuck and blair nate and serena dan and vanessa jenny and georgina <3
| Feb 12, 2010 7:27PM EST
Definitely CHUCK and BLAIR!! They are amazing together; but I do want to see a little bit of the fun Chuck back. Also I kind of want to see BLAIR and DAN... I know itz weird and probably won't ever happen; but still they would be very interesting. As for Serena and Nate. That could be interesting; but Dan and Serena are better. And Jenny and Vanessa... well, I really wouldn't miss them if they weren't there. BUT I hope CARTER comes back! Maybe with Blair?!? or Serena?
| Feb 12, 2010 3:37PM EST
chuck and blair!
| Feb 12, 2010 3:23AM EST
errr for some reason... i can't stand nate and serena... it's all a bit too mushy mushy if u kno what i mean -_- i guess there's no question for chuck n blair... i just cant see it any other way but jenny and nate were great together and i agree with a lot of people here. DAN AND SERENA just have that connection... u can try pairing them with other people, it wont work, its just like ryan and marissa of the oc u know :( please get rid of vanessa OMG... she was the reason jenny and nate didn't work (its funny that the blame was on jenny when vanessa was the first one who lied about the letters), she was the reason dan and serena almost didn't work, she was the reason dan and whoever it was that hilary duff played didn't work, she almost jeopardized chuck n blair when she slept with chuck... OMG pleaseeeee get rid of her or at least make her a villain... dun try to make us like her! grrrrr!!!
| Feb 11, 2010 7:59PM EST
Well... Chuck and Blair are definitely a great couple! But I'd also say that Serena and Nate are very cute together!!
| Feb 11, 2010 12:18PM EST
Why all the Vanessa hate?! Not only is she GORGEOUS, her character is awesome. She empowers women; shes strong, independent, intelligent, with a sweet of my favorites!! I think she should end up with one of the upper eastsiders...Nate preferrably - he's...BLAZIN.Chuck and Blair are the perfect couple.Dan & Serena were great together.Jenny...with a new hottie.
| Feb 11, 2010 3:21AM EST
Chuck and Blair Nate and Jenny Dan and Georgina Vanessa becomes a lesbian :) and I dont care what Serena does.
| Feb 10, 2010 11:22PM EST
Chuck and BlairNate and JennyDan and Vanessa
| Feb 10, 2010 9:07PM EST
Nate and Serena I've been waiting for them since the first sentence, I'm trying to remain patient for March.
| Feb 10, 2010 3:26PM EST
Chuck and BlairNate and SerenaDan and Vanessaat the end of everything for nowchuck and blair (of course): would be bad when they really break up, needed a million episodes to get togetherwant dan and hilary duff backjenny should hook up with that drug guy, she's playing with
| Feb 10, 2010 1:06PM EST
chuck & blairnate & jenny
| Feb 10, 2010 10:52AM EST
Nate and Serena!!!
| Feb 10, 2010 1:00AM EST
Dan & Serena
| Feb 9, 2010 11:44PM EST
NATE AND SERENA!!!and chuck and blairand i cant stand dan nor vanessa so they can be annoying together
| Feb 9, 2010 11:25PM EST
Chuck and Blair.Serena and Dan.Vanessa and Nate.
| Feb 9, 2010 10:38PM EST
Chuck & Blair (:
| Feb 9, 2010 9:56PM EST
Chuck & Blair Nate & Serena Dan & Vanessa the end, cause those are the perfect couples of the show, if they break them up then the show wouldn't be so fun!!! ;P
| Feb 9, 2010 9:21PM EST
chuck and blair forever, loads of sexy time pls !serena and nate, for now that'll dovanessa killed off or sth, moved out somewhere else etc.dan and someone newgeorgina back and with some new boy/girl toyjenny not with the drug dealer, maybe some rock starish indie boy...perfect ! :D
| Feb 9, 2010 8:23PM EST
OBVIOUSLY CHUCK AND BLAIR!! the show was made for them!! And I think they should have Blair sing on the show XDThen Jenny and Nate, they were so intense in their 5 minutes togetherthen Serena and nobody because she isn't interesting in the slightest (but if she has to be with someone then Carter cause he's the only one that gave her a decent storyline).then Dan can be killed off cause I really hate him, he is so friggin' full of himself!! Also Vanessa is really boring too, I agree with others saying she should be with H.Duff that would be hot.
| Feb 9, 2010 7:44PM EST
C & B! Brill couple but brake them up...let's have a twist on the show. N & S...Zzzzzzzzzzzzzzzz!
| Feb 9, 2010 6:38PM EST
Chuck and Blair (!!!) <3Nate and JennySerena and CarterVanessa and Dan I dont really like Serena and Nate together, cause i just dont see the chemistry. Vanessa and Dan... i dont really know if i like them together or not, but i think we should give it a try ;)
| Feb 9, 2010 6:00PM EST
Nate & Vanessa= too cutteeSerena & Dan= fairy tail love, lonely boy and the Vanderwood(?) princesChuck & Blair= sexy mysteriousNate & jenny= secretive, mysteriously, and sensual but very lovely couple
| Feb 9, 2010 5:58PM EST
#1 couple-Chuck & Blair forever #2 couple-Nate & Serena #3couple-Dan & Vanessa #4 Lilly and Rufus
| Feb 9, 2010 5:50PM EST
Nate and Jenny Chuck and Blair Serena and Carter Dan and Vanessa I hate Serena and Nate together. and Dan and Serena are brother and sister thats gross!!!!
| Feb 9, 2010 3:04PM EST
Chuck & BlairNate & Serena Dan, Vanessa and Jenny need to find themselves new ppl!!!
| Feb 9, 2010 2:41PM EST
Nate and JennyChuck and BlairSerena and Dan
| Feb 9, 2010 1:54PM EST
Nate & Serena are really the best! <33
| Feb 9, 2010 1:33PM EST
Chuck & Blair, Brake up. Am I the only one which wants the show to be how it was at the beginning. Chuck being an asshole/playa and Blair being a totall bitch, omg this show is getting lamer with every new episode its like watching Big Brother or smth. Chuck cut your hair and stop acting like 70 year old.
| Feb 9, 2010 1:26PM EST
CHUCK & BLAIR!!!And then Nate & Jenny and Dan Serena. Nate? With me!!!
| Feb 9, 2010 1:15PM EST
Chuck and Blair & Dan and Serena!
| Feb 9, 2010 1:01PM EST
Chuck and blair , dan and serena and nate and jenny
| Feb 9, 2010 12:40PM EST
Chuck & BlairNate & SerenaDan & Vanessathe end :P
| Feb 9, 2010 12:18PM EST
Chuck and Blair obviously!!
| Feb 9, 2010 11:58AM EST
Nate and Jenny but not yet, i want them to get together on the last episode or like season 4. Chuck and Blair obviously but i want more of the old chuck back. I think serena should be with no one for a while then in like season 4 find the love of her life and stick with them like chuck and blair.
| Feb 9, 2010 11:45AM EST
Chuck and Blair, Nate and Serena, Dan and Vanessa :)
| Feb 9, 2010 11:31AM EST
Chuck & Blair
| Feb 9, 2010 11:29AM EST
Nate & Serena and Chuck and Blair
| Feb 9, 2010 11:00AM EST
Chuck and Blair! For sure!Then Comes Nate and Jenny.And then Dan & Vanessa. Serena can have the pick of the litter for all I care.
| Feb 9, 2010 9:55AM EST
Nate & Serena <3 <3Chuck & Blair <3Dan & VanessaEnd Game.
| Feb 9, 2010 8:14AM EST
Chuck and Blair, Nate and Jenny, Serena and Carter and Dan and Vanessa, or Dan and Serena. Although actually I like most of the pairings on this show, those are just my ideal ones. The only ones I really don't like is Vanessa with Nate or Chuck.
| Feb 9, 2010 7:33AM EST
Nate and jenny
| Feb 9, 2010 7:14AM EST
Chuck & Blair!
| Feb 9, 2010 6:36AM EST
Chuck & BlairNate & SerenaDan & Vanessa
| Feb 9, 2010 6:04AM EST
chuck n blair, nate and serena,
| Feb 9, 2010 5:23AM EST
Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair Chuck and Blair <3 Foerver
| Feb 9, 2010 4:56AM EST
Blair and Chuck, Nate and Jenny and Dan and Serena.
| Feb 9, 2010 4:49AM EST
Def. Chuck n Blair! <3Hopefully Serena and Nate, even tho that would be kinda boring...
| Feb 9, 2010 4:42AM EST
chuck and blair others dont matter haha
| Feb 9, 2010 4:38AM EST
N and S. Hotness. C and B. Again, HOTNESS. But I want Carter back. XD Ayee. I want Carter with like.... a model or something.
| Feb 9, 2010 3:49AM EST
chack and blair forever. nate and serena. dan and georgina. jenny and a new hot boy to drool over. and i was thinking a good twist would be vanessa and hilary duff seeing they kinda hooked up already.
| Feb 9, 2010 3:34AM EST
Chuck & Blair - Perfect power couple Vanessa, eww kill that B* off, make sure the trash stays out of Upper East side. Nate & Serena because there is so much hotness in that couple that it makes me a little uncomfortable.----- Jenny & Nate would never work they are too brother/sister but with a little bit of west virginia. Dan needs to find someone else who doesn't mind his self-righteousness; I vote to bring back H-Duf because "Why Not?" ***Anyone who gets that reference kudos to you and more embarrassment for my life. Don't you love the interweb?
| Feb 9, 2010 12:27AM EST
chuck and blair
| Feb 8, 2010 11:31PM EST
Chuck and blair, as long as we get a bit of the old chuck back, and a lot less of the old blair. She really needs to grow as a character, instead of pretending she's still in school. Dan and Serena, I still live in hope. I think they are like one of those couples that how ever for away from each other they get, they suit each other the most and the show actually works best when they are together. Basically like what Ryan and marissa were for the OC. I actually feel a huge amount of the shows problems could be solved by bringing them back together. It would certainly bring serena back down to earth. I've hated her story lines recently. Nate & Jenny, they were only an item briefly but they were definitely a good couple. When jenny matures a bit they should end up together.
| Feb 8, 2010 11:02PM EST
Blair and Chuck, Nate and Serena or Jenny, Dan and Georgina. Vanessa out, or please make her be less boring!
| Feb 8, 2010 10:41PM EST
Nate and Jenny again, plz!!
| Feb 8, 2010 9:15PM EST
Chuck and Blair for life! <3 <3 <3
| Feb 8, 2010 8:35PM EST
Definitely Chuck & Blair the rest can do whatever they want~~

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