Chuck and Blair on "The Wrong Goodbye"

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 at the Pilot

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.

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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!

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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?

Camila Miranda
Student from Brazil who loves books, TV, movies and the Internet, of course. I also love writing and drawing. My favorite tv shows are Fringe, Friends, The Vampire Diaries, Gossip Girl, Supernatural, Smash, Glee, Lost, House, The Secret Circle and Pretty Little Liars.
  • Manda

    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.

  • Sarahlynnl200

    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

    • Chris

      oh baby are we watching the same show? have you seen chuck?

    • Redehcoolus

      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.

      • Guyzrhot123

        totally AGREE!!! (secretly hoping he dies in the car crash)

      • 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. 

  • Allie

    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.

  • I love how in all of these spec posts online, Louis is a non-factor. Ees nah fehah.

    • Sarahlynnl200

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

      • Redehcoolus

        You’re the reason so many people hate Chair fans. Delusional and opinionated about it.

        • 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. 

        • guest1

          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.)

  • Eugenia Polegri

    I’ll b honest, at first I thought Chuck was gonna end up being gay or bisexual (because of the book) and I think that would have made a better storyline (Chair happened but then around season 3 chuck started having feelings for nate or another gay friend he met) 😛 I mostly think this would have made a better storyline probably for selfishness (I’d LOVE to see chuck kiss another guy again!) but since it’s a little too late for that (and let’s not forget a lot CRAZY!) I think it would be better if maybe, MAYBE Chuck ends with another woman, and not w/ blair (maybe they get marry but blair cheats w/ a co worker at W) and after a few years Chuck meets this amazing, gorgeous and smart art dealer on a trip to paris (actually, when I grow up I wanna be an art dealer and I live in Paris xD lol) and then he starts falling for her, etc.. I just know that chair is one sick relationship and the more they are together, the more they hurt each other (but ofcourse if it wasn’t like that, then we wouldn’t be hooked!). Since the beginning we knew that chair will end up being end game (they have spent the las 5  season doing the same storyline!), it’s just undenaiable! Still there’s a low chance of them NOT ending up togethere. Well, I think we will just have to wait and make lemonade with the lemons we have =)
    P.S.: Me and my friends LOVE your blog<3 

    • Eugenia Polegri

      hahaha I’m a 14 year old girl with a LOT of super crazy theories (In case u haven’t seen my comment about charlie being chuck’s ex lover) xD lol Can’t wait until January 27!!!!!!!! <3<3

  • Chuck and Blair will end up together!!!I think that at this point it’s the most obvious thing in GG and after the last episode I don’t have a doubt(and not only because I’m a Chair shipper)!!!As for Derena I really don’t know what to think b/c there are times I strongly believe they are endgame but then again there is a possibility that Dan will end up alone!:?So we’ll see how it’ll play out….

  • Veronica

    Lots of interesting ideas! I’m a Serenate fan personally, but it’s looking pretty grim for them ATM. Serena seems all about Dan, and they were the original couple from the pilot, so I bet they end up together. And the alternate scenario for Chuck makes it pretty obvious that he and Blair are endgame, no way are they pairing him off with a 4-ep guest star. So I can’t really see Blair ending up with Dan under any circumstances. Sad for Nate tho, there’s no one left for him 🙁

    • I know Chair is endgame. I just did an alternate ending for all of them because I was thinking about it. And it’s nice, you know, for Dair shippers that actually like Chuck to see that he could end well. (:

  • Andy

    Funny how all Chair fans are absolutely convinced that Chair are endgame.
    If that’s the case why do you guys spend your life threatening the writers on twitter? Thought it was in the bag…
    Anyway, I don’t know who will be endgame because unlike the majority of lucky posters here, I cannot see into the future. I’ve tried. Don’t think it’s working.
    Frankly I don’t think the writers have decided yet either. What they are doing now is building a nice little CBDB triangle to stretch all the way till end of S6.
    If it were up to me it would be Dair, as you may have guessed already…
    I don’t know the rule about endgame being the longest running couple on the show. In creative writing you can take the story in different directions and change stuff around.

    • We don’t see into the future. This is pure speculation made for fun. And sure it’s not a rule that the longest running couple is endgame, but after last episode can you really say that Chair is not endgame? “You are all I ever wanted.” “I love you.” “I love every part of you.” Those quotes made it pretty clear where Blair’s heart lies. I’m not trying to convince you of anything, that’s just Chair fans opinion about how the show will end.

    • Actually, in creative writing, it’s generally a good idea to have your story actually planned out… as opposed to just wandering aimlessly and seeing where things go, which results in muddled plots and uneven characterization. And the producers have said multiple times they have a long-term plan/”finish line” in mind, all we’re doing is speculating about what it might be. Of course it’s always possible they could pull a 180 in upcoming episodes, but based on the last four years, the writing seems clearly aimed towards a Chair endgame. 

    • Right of COURSE IT SUCH BAD WRITING to have a clearly built love story and endgame in mind….thats why half way through Pride and Prejudice Janes said “hmm you know what we have had six chapters of Mr Darcy and Elizabeth lets veer off and have Elizabeth hook up with Bingley”- oh wait?

      Maybe you need to take a lesson in creative writing or read an actual book most love stories or stories in general have coherent plot point A to point B in mind. Thats is essentially story telling. Sure the muses might cause tweaks here and there or change details’sceanrios around, but in essence most writers have a general knowledge of where they intend the story to go- an Endgame.

      And YES most television show writers- at least the good ones- also have plans or mapped out ideas of where they want the show to go even if the change or explore new ideas here and there. Think Carlton Cuse and Damon Lindelof in Lost for example. And the GG writers have said MANY times that they have LONG TERM plans in place for the show and they have endgames in mind.

      I find it amusing how DBers in the same breath bitch at CB fans about the writers not having plans or sustained story and changing directions (even though that contradicts what the writers themselves have said anyway) then going on about how DB were FOUR YEARS IN THE MAKING! and not something the writers pulled out of there ass in the fourth season to get people riled up.

      And for the record the reason CB fans get so annoyed by the writers treatment of CB is NOT because we are all soooooo threatened by DB. Its because we are so sick to death of the stalling and fucking around with CB, keeping us all baited and hooked while they go around playing musical chairs with other pairings just for the reward of CB being endgame. Because believe it or not pretty much 90 percent of CBers are interested in the journey being rewarding for CB and them being given a good storyline so that we will feel actual satisified when we DO get our endgame. We have been put through so much crap and game playing by the writers already. We want to know by the time the writers actually put CB together in a clear way that we will still care, and that all the rubbish we sat through- the indecent proposal, Blair having sex with Chuck uncle, DB/NB flirtations, Chucks numerous downward spirials- wont just be for a half assed last minute reunion. We are not just interested in them getting a shot- everyone else be damned.

      Also I particuarly are getting fed up of DBers basically acting like the only reason why people want or ship CB is because “they are the longest running couple” and we somehow dont appreciate good story telling or care about the shows story trajectory- like its inconcievable that Chuck and Blair actually ending up together COULD BE A SATISFYING AND GOOD ending to the story……but a very brilliant person wrote all my thoughts on this MUCH better so ill just let her say it:

      • I find it hard to believe you read a lot because you’re terrible at stringing sentences together. That was painful.

      • Grand Social

        I’m sorry, but you fail to grasp what “Andy” was saying. Yes, obviously having an “endgame” is beneficial to story-telling, but it is indicative of lazy/bad writing to have one dimensional characters that follow an idealist actions which would be completely implausible when applied to the real world. The Gossip Girl characters are for the most part, well fleshed out, three dimensional characters (especially Blair, and with the exception of Serena, although anyone with any sense of understanding writing style will know that that is the point of her character in the novels, to act as a caricature of the beautiful, vacuous upper-east side princess who gets everything she wants, even thought Blair is more deserving)

        As three dimensional characters who have developed phenomenally over the course of the last five years, you can’t expect them to not learn anything from their experiences, and just follow their “hearts.”

        Why do you even want Chuck & Blair to be together so badly anyway? They actually made for a terrible couple. Season three, when they were together was absolutely horrible, in terms of both characters had become boring and untrue to themselves. There is no denying that Chuck and Blair have great passion, but that is really all that they have, and for those of you who don’t read the twilight books, you’ll know that passion works both ways, creative and destructive. I mean, look at what Chuck has done to Blair, he has repeatedly broken her heart. He refused to tell her he loved her. I happen to remember in the first season, after she’d broken up with Nate and had given Chuck her virginity that told her “you’re like the Arabian my father used to own. Rode hard and put away
        wet. I don’t want you anymore, and I can’t see why anyone else would.
        ” HE SOLD HER FOR A GOD DAMNED HOTEL!!? He slept with Jenny Humphrey? Have you all just forgotten this? Why would you want a character you supposedly care about to end up in a relationship like this? If your best friend had been put through everything that Chuck put Blair through would you want her to be with that guy? Anyone who says that they would, would be lying. You can’t even make the argument that the characters aren’t real because every writer knows that your characters are real, but that you created them. If Chuck and Blair get back together it would be unrealistic, and only done to please the myriad of immature fangirls who for some reason fail to see how unhealthy the relationship is and it would therefore be bad writing.

        “We somehow dont appreciate good story telling or care about the shows
        story trajectory- like its inconcievable that Chuck and Blair actually
        ending up together COULD BE A SATISFYING AND GOOD ending to the story”
        – No, I don’t believe Chair shippers do appreciate good story telling, because if they did, they would embrace the character development that has occurred and realise that the CHAIR relationship is a passionate, doomed one. I’m not saying it wasn’t one hell of a love story, but it was a doomed one. Some of the best are, but every doomed love story has to end eventually. They will never be happy as long as they are together. Given their previous make-up/break-up train they have only ever been on, shows that this would not be a “satisfying” or “good” ending to the story because it would not end the story, Chuck & Blair would continue of their dysfunctional “love-hate” cycle until one of them develops an alcohol problem, the other the prescription med addiction and they age together bitter and despising each other. (This would be a brilliant end to the story if GG was a critique of the Upper East Side as Humphrey’s “Inside” was, but not for GG)

        Yes, the writers said that they have a definite endgame in mind, but they never said it was a CHAIR-based endgame, all the CHAIR-shippers seriously need to stop going “CHAIR IS ENDGAME! THE WRITERS SAID SO!!!” because they said no such thing, they have an endgame, meaning that its something that they’re working towards, setting up to pay out in the future, which could be anything, so seriously, grow up and stop attacking the DAIR-ers.

        I would like to point out that I am ship for neither couple, I merely want to show to continue and end on a high note, and I want the characters that I care about and have invested time in to be happy. From a subjective point of view Dan & Blair make a much better couple, in terms of their shared interests, and their socioeconomic differences. To be honest, I would see them being together as a much more satisfactory end to the story, showing that two people from different backgrounds who hate each other due to those differences, learn to look past their differences and see the person that’s on the inside, to realise that their flaws are only due to their circumstances, come to see not their differences, but their similarities and fall in love. Sure as hell beats the crap out of the “every girl loves a badboy” story that Chuck & Blair represent.

  • MW

    Objectively, Chuck and Blair could end up together but if the writers want to give them a tragic ending, they would not hold back I’m sure. But I’m crossing my fingers for them to have the ending they deserve, hence happy and powerful TOGETHER! For Serena, I want Carter to come back. They were prefect in S3 and IMO this guy loved her more then any other dude on Gossip girl, for who she was and never judge her unlike Dan especially. For Humphrey, heh, I’m not worried about him, he will probably fall in love with an other damsel in distress like he does pretty much every year. As for Nate, maybe, me…?

  • I want NJBC babies at the end (Chuck&Blair, Nate&Serena) <3 Dan can go to Barcelona and climb out to Vanessa's window. They did this combination in S3 and it felt greatly right alltogether. It was great =)

  • Good article. I think its interesting to speculate on okay- if your couple is the one who finishes the show together. well then what happens to their other options. I think its particuarly relevant with DB because with them getting together it leaves big gaping holes for their alternative options of Serena and Chuck. There is really no where for them to go as characters and it sort of leaves their stories and their themes pretty much gone with the wond (for instant Chuck’s desire for happiness and a family). I mean the fact that the person who could come back for Chuck- Eva- is just a very unlikely option shows that the writers have built the essence of the show with CB endgame in mind.

    I mean at least with Chair as together in the end Dan and Serena are the alternative pairing for each other, plus Dan and Blair can/will always be very good friends since they do have a meaningful friendship to fall back on outside of romance. I think its very likely they will do a Dawson and Joey thing with DB where they will play the whole “we are soulmates- best friend soul mates” thing.

    I mean we all get tunnel vision with our couples/ships so its understandable not to see or care about what happened outside of that. I think for the show to REALLY be good you have to think about what works out the best FOR ALL the characters…..and not just in terms of romantic options but also the friendships and the family dynamics on the show to.

    Anyway good read 🙂

    • Thank you, I agree with you when you say that the writers have to look at the bigger picture. It was really hard to think of someone for Chuck if DB happened. Then I remembered Eva, but I sincerelly tried to think of someone else because it didn’t feel right. oh well, I tried, hahaha.

  • harum scarum


  • Celine

    I seriously love you righ not.  Dan and Serena need to come back.  Chuck and Blair forever!  Nate with a good girl.

  • Jackie

    You guys, don’t you realize what has happened in the previous episode (5×11)? Blair admits to only loving Chuck, and she says that she’ll never be able to love anyone the same way. Gossip Girl ends after season 6, she’s not going to automatically fall in love with Dan. Chuck has changed, and Dan needs to step back because he knows very well there is no chance that Blair will ever love him the way she loves Chuck… Dan himself even said that, “You two have some strange force field effect on each other. Physicists should study it.” Face it you guys, Chair is endgame.

  • Anonymous

    The endgames should be : Chair, Derena, and Nate with maybe the real Charlie? if shes nice and all 

  • what’s wrong with you people why are you such Dan haters, even if Chuck and Blair are endgame there’s nothing wrong with Dan I don’t think you people pay attention to the show if you watched the last episode you would know that the vows that Dan wrote for Louie made Blair realize that she wanted to be with the person who wrote those vows even if she doesn’t know its Dan who actually said all that yet. I think show could go either way Dair or Chair for the endgame. Chuck never would have wrote vows like that for Blair, and Dan and Blair have so much more in common and Dan would never hurt Blair the way Chuck has I am not a Chuck hater cause I love him to but come get real it could go either way you never know. The producers did say that they always planned on getting Dan and Blair together pay attention people. GO DAIR

  • ella

    Well Chair is obviously endgame but it can change. They may be the couple of the show but that doesn’t mean they are gonna end up although I’d love them too. Dan/Serena are so season 1. Nate/Serena are more likely to end up. That’s the pattern of most TV shows. The person usually ends up with the 2nd person she/he loved. But for me, It’s Chair/Serenate for me. I dislike Derena. I love Dair also but I’d much prefer if the NJBC end up together. I don’t really care about Dan. But here is what I will really love: Chuck/Blair, Nate/Serena, Dan/Vanessa. That’s the way it’s supposed to be. It’s TRIFECTA!

  • J003838

    Blair and Nate, anybody?

  • Why the hell do people keep insisting on Dan and Serena?? THEY’RE STEP SIBLINGS, YOU SICKOS.

  • I’ve always thought that Dan was gossip girl for some reason, think about it hes an insider thats aways been an outsider or maybe thats just what the show wants us to think? it could be eric or even a forgotten dude like carter basin. nm but i was seriously disappointed with lily choosing bart. rufus was her love and they r fucking married not a choice between who to date, i mean all those years of dead bart and suddenly lily decides to end her marriage with rufus and stay married to resurrected asshole bart bass! And for serena i think right now shes just irelevant, even nate is more involved which is weird! everything is so F-ed up …

  • Katherynnnn

    Okay, no doubt chuck and blair will end up together. Their just meant to be. Dan and serena on the other hand, might go on in season six, but I dont think their meant to be, I think dan and vanessa really click. NATE AND SERENA <3 I love them together!! They HAVE to be together. Their PERFECT! If their not, im going t be SO mad 🙁

  • i want chair, derena and natessa for gods sakes theyre perfect! please nate and vanessa get back togetherrrr

  • Serenator

    Serena is the one thing Nate has always wanted but can never have..
    I’m rooting for them. They have or had this connection that no matter what can’t be broken.
    Serena, Nate, Blair, & Chuck. Serenate & Chair, just like it’s always been.
    I mean, they grew up together! What happened to that childhood love?
    NJBC! The 4 of them have a long history together. I adore Chair & Serenate.
    Personally, if there wasn’t Dan and the other people from Brooklyn in GG then I would’ve loved the show.