Gossip Girl First Look: Blair Plays Cupid on Valentine's Day -- But for Whom?

Love is in the air on the Upper East Side, and we’ve got a sneak peek of the Gossip Girl crowd celebrating Valentine’s Day with some surprising results.
In the Feb. 13 episode “Crazy, Cupid, Love” (The CW, 8/7c), Nate throws a bash for V-Day, where his guests — including the real Charlie — wear Constance Billard-like outfits. Is the theme, “Love is hell like high school”? Or perhaps the get-ups are all part of a scheme? After all, Georgina is also there, chatting with Dan and Chuck.

Gossip Girl Exclusive First Look: Dan and Blair Take Flight (or Do They?) in Episode 101!

Elsewhere, “Blair can’t resist playing cupid for someone she loves,” while “Serena is shocked by something she witnesses at the party,” according to official episode description. Is Blair trying to push her BFF and Dan back together? If so, he doesn’t seem to be having any of it judging from the super close shots of him and Blair. Maybe an admission of love from her ex to her best friend is the shocking thing Serena witnesses?
Check out the gallery below and hit the comments with your thoughts/theories.

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98 Comments
  1. tina says:

    Just give us Chair!

    • S says:

      Just give us Dair!!!

    • Putri says:

      Dair, Dair, Dair. The only reason why I’m watching Gossip Girl.

    • .... says:

      so he can slap her around more or sell her for his hotel.
      No thanks, she doesnt have to be with Dan but she shouldnt go back to douchy Chuck

      • Epiphany says:

        Stop being a drama Queen. Oh no Dan is your idol! Makes sense now.
        All the crazy drama brings out the crazy in people.
        The only thing in GG that makes sense is Chuck and Blair, and it has been for 5 years now.
        Please GG writers bring back the love.

        • Blue says:

          Epiphany,
          “Stop being a drama queen”? Really? In what way does … mentioning what happened in Chair’s destructive relationship make him/her a drama queen? You can say Chuck loves Blair and maybe he does, but there is still a LOT more Chuck needs to change before he can be in a healthy relationship with Blair OR someone else.
          Don’t get me wrong. I LOVED Chair before the writers dragged them through the mud. But what kind of woman would Blair be if she let all that happen and still got back with Chuck? What message does that give to women in destructive, abusive relationships?

  2. Marice says:

    There is zero reason for Serena to be shocked about Dan’s callous disregard for her feelings. She’s known about his “love” for Blair since 5.10, so… Whatever.
    I assume Blair tries to set DS up and D doesn’t care. Also, is he confessing his love in Chuck’s bedroom? Hilarious metaphor for how his feelings for Blair will always be surpassed and overshadowed by Chuck’s.
    Excited for Georgie, though. And Chuck’s scarf!

  3. Sabi says:

    Ok are GG seriously celebrating Valentines Day with Dair? Ok Im just gonna sit the next few episodes out so Dair can finish and Chair can get back together.
    K.Thanks.Bye.

    • yay says:

      bye then! I’ll be happy watching Dair!! :D

    • MSC says:

      Me too. Dair is so stupid and contrived! I’ll skip until I see Chuck and Blair

    • K. says:

      *waves* Ta Ta!
      And can you possibly “sit out” of the series permanently?

    • Yep says:

      I just cringe every time I see pictures of Dan and Blair. They are just so mismatched, IMO. Dan is so so boring and he’s bringing Blair down with him. I think she should be single for awhile after her sham of a wedding imploded. I’m going to sit the next few episodes out because the writers seem to be directionless and there is nothing worse than watching a show you enjoyed flounder. It’s painful.

  4. nrs says:

    I bet Blair tries to play Cupid to Serena and Dan, but Dan won’t be having any of it and to get Blair to stop finally either kiss her or confess his true feelings for her. But let’s be honest, Blair won’t be having any of that because Chuck is the one she loves the most, as we keep getting assured episode after episode. She’ll just continue to use Chuck as a loyal lapdog like always.

    • mimi says:

      I think you mean Dan as a loyal lapdog, which has been this entire time.

    • Z. says:

      I was thinking the exact same thing. Blair gonna try and set them up and Dan is going to get mad and confess and be pissed cause he is always back-up in the eyes of Blair.

  5. Abby says:

    This show is a hot mess, but I can’t stop watching.

  6. sasha says:

    Serena better don’t ruin Dair! Love the 4th pic

  7. stephanie says:

    wow. for the first time in a LONG TIME I’m actually excited to watch Gossip Girl. Dan and Blair’s relationship is like a breath of fresh air on a show that’s frankly become tedious to watch. If it isnt recycled story lines about schemeing or backstabbing, its about Chuck and Blairs endless break up and make ups. Dan and Blair’s relationship is about the only thing that make sense on this show anymore.

  8. Allie says:

    LOL, agreed, this show is such a hot mess. I guess Blair will try to set up Dan with Serena, and he confesses his feelings for her instead (in Chuck’s bedroom, no less- very classy), and Serena overhears. So the only mutual love going on is between Chuck and Blair, but they can’t be together because Blair has lost her mind, I mean, made a pact with God.
    Okay, show.

  9. Ken says:

    the real charlie is super hot

  10. Allie says:

    It looks like a lot of red in the picture that Georgina is showing Chuck. I’m guessing she’s showing a pic of Blair and Dan. I’m looking forward to it, as I always liked “opposite attracts” story lines.

  11. Antonia says:

    This Valentine’s Day ep. look like a joke.
    Love that Chuck has his old scarf on (!!) but I would have loved pics of him with Blair. Duh. We need Chair on VDay for once!!

  12. Roxie says:

    OMG!!! Chuck’s scarf is BACK!! yay! Other than that, not really interested.

  13. maria. says:

    I’m a Chair fan and I’m not a bit afraid of this. Why oh why? Because it’s ridiculous to think Blair would kiss Dan in Chuck’s bedroom.

    • mSC says:

      Oh a joke for sure. Dan needs to cut his hair too, he looks like a slimy stalker and I bet Blair is like WTF? She’s trying to get DS together and then the animal on Dan’s head kisses her. Poor Blair. Chuck’s scarf is the only thing to look forward to.

  14. donna says:

    everyone looks amazing…highschool days yayyyyyyyy and yay for Chuck’s signarute scarf <3 Love himmmmmmmm
    I hope Chuck&Blair share scenes they are at the empire <3

  15. Startled says:

    What the hell is going on with Dan’s hair?!

  16. P says:

    Dear Santa,
    Would someone PLEASE cut Penn’s hair?
    ;-;

  17. Kelly says:

    Man, with all this Dair being thrown at us, I might just have to put Gossip Girl back on my DVR! I cannot wait :)
    P.S. Is the photo Georgina showing Chuck in picture 7 of Dan and Blair kissing? ‘Cause it sure looks like it to me!

  18. Sims says:

    Dair FTW!

  19. Joanna says:

    I only see the return of Chuck’s scarf!!! Anything else is obscured by Dan’s horrible hair and tactless manners.

  20. cbanks says:

    I just think it is funny that Dair fans think it is going to last or something. If she had real feelings for him she would have already figured it out. Now she is just using him to get past everything that has happened. I bet she does try to play cupid with Serena and him. I bet that will really upset you Dair fans.

  21. Alison says:

    Anyone else noticed that in the picture of Georgina and Chuck that she’s showing him a picture of Dan and Blair?!

  22. dani says:

    These are amazing, can’t wait for the ep and more Dan and Blair!

  23. maggie says:

    I think this is the episode where Dan tells Blair how he feels about her and I bet she is like ” Wait, what?? ” because she thought he was her friend only and she is trying to set them up this episode. I bet she pushes the issue and dan just blurts it out and that is when serena comes in to the room. Can I say predictible!? Serena will be pissed just because she isn’t getting what she wants and it looks like Georgie is trying to manipulate chuck but because he has grown he will hopefully take a different approach to seeing a picture of Dan and Blair together. Prolonging CB reunion because lets face it, you know it is coming. Does chuck back off or does he fight for her? that is a question I would like to know! I am thinking the latter ;)

  24. Wrenn says:

    Thanks for the pics. I love the pictures of Dair. I don’t care about endgame. It’s all about the journey for me and I believe that Dair’s arc is the best written on the show. I’ve shipped a lot of other couples who didn’t end up together and I didn’t stop once it was over. So throwing around the endgame stuff Chair fans isn’t going to make Dair fans go away.

    • lol ok says:

      And the journey crap isn’t going to make Chair fans go away. So how about we focus on our own ships and stop with the mocking and replying to comments that have nothing to do with us?

      • Wrenn says:

        I’m not trying to make Chair fans go away. I wish they would since they send death threats to writers and wish that they would get aids. It’s just a show. I wish we all could enjoy what we enjoy without get all crazy about it. I did enjoy Chair, but dude sold her for a hotel and then tried to make it like it was her fault. I love Blair and I want her HAPPY. If she won’t be with Dan. Then let her meet another good guy or be alone and let her go back to school and do something with herself.

  25. guest says:

    hope there some love of chuck and blair!

  26. K. says:

    Holy. Crap. These are so amazing if I think what’s happening in them is happening.

  27. Rachel says:

    Please cut Penn Badgley’s hair, but I’m so excited, I need another Dair kiss soon or I’m gonna go crazy

  28. Jenn says:

    WOW, for the first time in a long time, I won’t be watching GG. I’m tired of this ridiculous dair crap that makes no sense. Blair MUST have feelings for Dan, because she told her BFF to tell him her feelings, and has repeatedly said how she only wants to be with Chuck. Yes, that is the beginning of a beautiful relationship. There is nothing like hearing the girl you’re “supposedly” in love with, say how she feels dead inside without another guy. Gossip Girl writers are complete crap. This show or any of the relationships make NO sense.

  29. Danielle says:

    Dair is kissing on the phone that Georgina is showing Chuck. Look closely!!

  30. quinn says:

    hey… she has the ring she is with the prince and only Dan know about the deal and they are talking about it she feels horrible and finds Dan to be a shoulder to cry.

  31. H. says:

    Dair is the only reason why I’m watching GG. These pictures are just adorable! Love Dair!

  32. Clara says:

    Totally agreed! Great pics! aah, i can’t wait!! Dan and Blair should finally get together, best couple EVER! DAIR, dair, dair!!

  33. jennifer says:

    Omg, I’m so excited! They are soo adorable, I’m totally into Dair! So tired of Chuck Bass, Chair!

  34. u know u love me ;) says:

    b wants to push back together D & S, but then D tells her that he loves her, he kisses her, G take a photo of them and she shows it to C…
    btw, chair 4ever!!!!

  35. sarah says:

    yes! finally! awesome pictures!! Dair ftw!!!

  36. Erin says:

    UNFORTUNATELY…we know that Dan was at some point going to express his feelings to Blair. Whatever, the main issue I have is if he does this in Chuck’s room. Soooo TACKY, what a D-Bag! He should have grown some balls a long time ago, now it’s just pathetic! Now we have to watch this train wreck happen and wait for Blair to get it together and get back with Chuck, or not. She needs to get her head straight first before she gets with anyone!

    • Natasha says:

      Yeah, you’re right, it is tacky. You know what’s not tacky? Selling your gf to your uncle for a hotel. That is just pure class.

    • Ashley says:

      Lest we forget that when Blair and Chuck got together in Season 1 she was the on again/off again girlfriend of his best friend. Super classy.

  37. Kate says:

    I want chuck and Blair !! this Dair thing is really boring.

  38. dx says:

    yes dair…
    in other news.. Nate is having a new 2 episode reelationship yay !

  39. Andrea says:

    As usual, nothing will probably end up being what it looks like. I wouldn’t be surprised if Blair’s “affair” with Chuck officially started in this episode. It’s long overdue.

  40. dee123 says:

    Well i’ts Blair in the picture on Georgina’s phone you can see the red dress.
    Plus Serena is pissed about something. Why? Cause’ she’s crossing her arms.
    (That’s what she always does)

  41. l says:

    Hopefully Blair is just trying to help out Nate with RealCharlie.

  42. krayli says:

    Puh lease, everyone knows Chuck and Blair belong together! Dan is just the lonely boy from Brooklyn.

    • Natasha says:

      Lol u mad that super-classist Blair is most definitely going to be hooking up with Dan from Brooklyn? Your resentment is delicious.

  43. L2u9 says:

    I have a feeling that photo has Dan and Blair in it… Hopefully it’s time for DAIR!!!

  44. meg says:

    OMSGDFGDGDFGDFGDFGDFGDFGDFGDFGDFGGFDG
    Dan and Blair are the qtest ever.
    I can’t wait!!

  45. Jenn says:

    Ohmygod. Dan and Blair are so perfect I can’t even take it.

  46. ana muller says:

    There would be exactly nothing shocking about Serena witnessing Dan telling Blair about his ridiculous feelings for her. He already told everyone this, including Serena… hell he even wrote a book about it, where the two of them have imaginary sex and everything.

  47. Ella says:

    DAIR! Please, Chair? Come on. There’s only so much you can put a relationship through before it dies a certain death and Chair has been decomposing since mid-season 1, lol. Dan/Blair is the reason I tuned back in to season 5, having zoned after Nate/Blair ended in season 2. Looks like a picture of Dair on Georgina’s phone too…

  48. Chiara says:

    Blair plays Cupid for someone she loves … Serena, Dan misunderstands, Dan kisses (maybe) Blair, Serena sees them and she is shocked, Georgina sees them and photographs them. Serena gets angry, then she confronts with Blair and they fight, Georgina shows the photo to Chuck who is angry with Blair. Blair refuses Dan and she runs away ….. boring boring boring.

    • danielle says:

      If that’s the case… didn’t they do the exact same episode, where Dan/Blair kiss. Serena and Chuck are pissed about it. Blair says she actually feels nothing for Dan. THAT WASN’T EVEN A WHOLE SEASON AGO. Now gossip girl has gone from recycling conversations to repeating entire episodes, just cancel it already!

  49. harum scarum says:

    wow, so dair get 2 valentine’s day episodes in a row? do the writers even know what that day stands for?
    ah well. i just hope we get back the endgame couples soon because this show is getting painfully dull without them.
    CHAIR AND DERENA FTW

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