Gossip Girl: A few endgame theories

Chair and Dair. Apparently, Gossip Girl has become the Blair Waldorf’s Love Life show. I ship Chair and, for me, they’re “endgame” (meaning they’re going to end up together before the series is over, in case you don’t know), but the other day I was thinking about how many Dair fans are out there and some questions came to my mind: What if the Gossip Girl writers decide to make Dair happen in the end? What would happen to Chuck and Serena? And what if Chuck and Blair end up together? Will Derena be back on? And after all of those questions, another one popped into my head: What the hell happened to Nate’s love life?!

So I came up with some theories. All that I’ll write here is pure speculation. It’s also spoiler-free for those who have watched all the episodes that aired thus far.

If Chuck and Blair end up together…

Serena waiting for Dan in the Gossip Girl pilot episode.

If Chuck and Blair ended up together, Dan would probably turn to Serena for comfort. They’d begin to hang out more and as Serena’s rekindled love for Dan grows, Dan would begin to see for himself that Serena is the one for him. However, feelings don’t just go away, it takes time, and he can’t just erase Blair from his heart. Serena would notice that and be jealous and they’d fight. Dan would finally realize that Serena’s fallen in love with him again and forgive her for her behavior. As they get closer, their love would grow. For me, season 6 (yes, I believe there will be a season 6) could be about that (and Chair’s relationship , obviously) and the show could end with them being together again, in a date, like in the pilot (pictured above). Even with the same clothing, to remember the old times. As I write this, I can’t stop imagining it. I’m sure we all – even Dair fans – can imagine that scene.

But then there’s Nate. What if Serena got tired of waiting for Dan and decided to try it with Nate one more time? Though I don’t have much to say here, we know it’s possible. I’m pretty sure Nate would agree with Serena if she said “hey, Nate, let’s give our relationship another try!” Maybe he’d be reluctant but would end up wanting to give it another try too. I guess if that happened Dan would end up with Vanessa… if he ever forgives her. If he doesn’t, I don’t know, maybe he’ll end up with Chivy. Or maybe the real Charlie Rhodes shows up and he falls in love with her. If none of these happens, I’m sure he’ll find someone or at least find a way to be happy.

If Dan and Blair end up together…

Dan and Blair watching movies and talking on the phone.

If Dan and Blair end up together, they could always bring Eva back. If you don’t remember Eva, she was the blonde French girl who saved Chuck’s life in the beginning of season 4. In my opinion, Chuck has never loved anyone as much as he loves Blair but he loved Eva back then. Sure, Chuck would be devastated after losing Blair again. He would drown himself in alcohol and women for a while, before he realized it wouldn’t do a thing for him. He’d begin to think and probably remember Eva. With luck, she’d be available and willing to accept his apology and then they’d be together.

And what about Serena and her love for Dan? Well, do you remember her other love? Nate? The love that started the whole series? Yes, Nate! What happened to Nate’s love life, by the way? The seasons passed by and he kept making out with older women. Maybe it’s time for a change. This is like my first theory only the other way around: Serena would turn to Nate for comfort and Nate, being the sweetheart he is, would comfort her. His feelings would return (I don’t believe they were ever really gone) but Serena would be all “I love Dan now I lost him! Dan. Dan. Dan…” However, Serena had to choose so many times between the two guys that I don’t believe she could spend much time with Nate without falling for him all over again. Happy ending for Serenate fans!

If Chair and Derena end up together…

I mean, what will happen with our older-women-lover sex god? I’m betting on Jenny (if Taylor Momsen would come back). Yes, she’s in London studying fashion but she does have a family in Manhattan and she can always come back to at least a few episodes to visit Rufus and Dan. I guess everyone has apologized to her by now and she could bond with Nate once more. I’ve always liked their little relationship and I’ve always thought it could be shown more than it actually was on the show. It could all happen in the end of season 6. Chuck and Blair are together, doing whatever they want, maybe even planning a wedding. Dan and Serena are hanging out, getting close again, falling in love. And Nate and Jenny are spending time together and eventually dating. With the right writing, it could be the old times again, when the show was focused on the six main characters.

Oh well, I’ve created so many theories I could write fan fiction. Maybe they’ll happen (I wish some of them would), maybe they won’t. Tell me: what do you think will happen?

View Comments

  • I think Chair will end up together but I'm not sure about Derena. I think Danessa made the most sense, so maybe Serenate should get back together and Lonely Boy can chase down Vanessa in Spain.

  • Chuck and Blair will end up together and hopefully Nate and Serena.  Dan can either end up lonely which I prefer are he can try to make amends to Vanessa. Though the way Dan treats people I really want him to end up alone

    • Hahahahahahahaha. The way DAN treats people? Compared to Chuck he's an angel. He's never tried to rape anyone, never tried to trade anyone for a hotel, never almost hit a woman. If anyone needs to be alone - or dead - it's Chuck.

      • I agree with you Dan does not treat people badly not like Chuck does when did that person draw to that conclusion its ridcilous Dan's a hell of a lot nicer to people than Chuck is

      • EXCUSE ME. Chuck has grown a lot as a character since season 1, in case you haven't noticed. He was a complete pig back then, but now he's a lot more respectable than Dan. And please remember the only reason Dan and Blair are together right now is because she married Louis-to save Chuck's life. Remember the first time Dan and Blair kissed? She said it was "LIFE CHANGING"! Oh wait...that's because it made her realize she'd always want Chuck.

  • I don't really doubt Chair as endgame. But the whole Serenate and Derena thing interests me. There, I think it could go either way. 

  • I think Chuck and Blair will end up together for sure (after the last four years and especially after the last episode, nothing else would make any sense). I think Dan and Serena will too, but they have a lot of rebuilding to do, after how Dan has treated Serena lately. As for Nate... I think he could've ended up with Jenny if she were still on the show, but now I think he'll probably end up either alone or with Ivy. 

  • Well chair is obviously that will end up together( except the 10000000075840 reasons the show has show us,the Gossip Girl writers/producers have pretty much say it "we are keeping the finish line"),now I believe they will bring Dan and Serena "close" for a while but S will finally end up with Nate (or maybe Carter?) and Dan if he doesn't go with Vanessa he'll probably stay alone ( lonely boy) like in his book.

    • Dan is a non factor too!  Just in the Dair fans heads and Dan's too.  Penn please get a haircut!

        • I don't hate Dairfans but to think that they are in the running to be endgame would be delusional. Not saying you think that because I don't know, but to me Dan is a non-factor in terms of endgame. 

    • Took me way longer than it should have to decipher your Louis-speak, heh.
      Poor Ivy gets ignored too, but I think she stands the best chance of distracting Nate from his cougar-hunting. Although, that would require him figuring out that she's not actually Charlie sometime before the series finale, and figuring things out has never been his strong suit. 

  • I think Chuck and Blair will end up together. They're meant to be and all the anvils of endgame have been dropped for them. Plus, they trended world wide, the fans want them.

  • Oh, and Dan should be alone because his "love" for everyone is so ridiculous. He's loved 3 mains so please. Have Serena with Nate or Carter.

  • chair for sure, dunno about serena though. probably she'll end up with dan because they keep bringing that up, serenate seems to be dunzo.

  • I have no doubt about Chuck and Blair ending up together. I used to be sure about Dan and Serena, but now I'm wondering if maybe they'll do more of a Ryan/Taylor-style ending, where it's implied but not explicitly stated, or they might just end it on an optimistic note for them. I don't really see Serena ending up with Nate, because that pairing's been completely abandoned- and she continually chose other guys over him (including his own married cousin), so I don't see it as particularly rootworthy anyway. 

    I would've liked to see Nate end up with Jenny, but I think Taylor Momsen's totally burned her bridges with this show, so that's not gonna happen. 

    • she could come back for one or two episodes as a guest star. they could always do a time jump too.

      • Yeah, that's true in theory, but the way Taylor left didn't seem very.. amicable, based on what was reported in the media. So I dunno, I would just be very surprised if she was willing to return. I really think the show brought on Ivy to be the new Jenny-like character, which is why they seem to be setting her up with Nate. 

        • Yeah Taylor's turned into a rockstar (and somewhat of a brat,  but that's beside the point, because its part of her rocker image now) and definitely wants to put her days with Gossip Girl far far behind her.  That's why its HIGHLY unlikely she'd return to the show no matter how much the producers may try to bribe her.  (Though my guess is that TM's parting from GG was on similar terms as Mischa Barton/'Marissa's' 'parting'/firing from The OC.  Though I think Taylor really wanted off the show.)

Recent Posts

On the precipice of Moonlighting’s downward trajectory

ABC's detective hit Moonlighting was one of the best TV show's of all time —…

5 years ago

‘The 100’ Star Marie Avgeropoulos Says Octavia Blake Doesn’t Need A Man (Or Woman) To Be Happy! Season 6 Is About Forgiving Her Sins

Previously Published on Fan Fest News...  For six seasons on The 100, actress Marie Avgeropoulos…

7 years ago

Becoming Josephine: ‘The 100’ Star Eliza Taylor Says Goodbye To Clarke… For Now

Previously Published on Fan Fest News...  It seems The 100 fans have gotten their own…

7 years ago

TV shows are not several mini-movies

I was browsing Reddit after the clock struck midnight on New Year's Eve (or what…

7 years ago

10 of my favorite shows of 2018

It's a little late, but I wanted to share a few shows I liked this…

7 years ago

Hulu’s ‘The Looming Tower’ star Mark Hildreth talks human heroism, and selfishness in US History

Mark Hildreth is a jack of all trades, with an undeniable passion for entertaining. Viewers…

8 years ago