Gossip Girl Season 5

Crazy, Cupid, Love


Ella Rae Peck  Kaylee DeFer  Michelle Trachtenberg  Nick Cornish

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Gossip Girl: Another picture perfect Valentine’s Day on the Upper East Side. And how am I going to celebrate? By exposing a giant secret today that’s sure to break more than a few hearts.

Dorota: Miss Blair! You’re back! I was worried you’d be locked away in big stone tower somewhere, and only way to speak is through smoke signals or coded messages on Twitter.
Blair: Thankfully, Dorota, we don’t need to learn Navajo just yet.

Dan: I was just coming by to pick up those Blurays I let Lily borrow. I thought maybe I could give them to Blair. I know she’s back from her honeymoon alone, so…
Rufus: So you figure that if you drop them off, maybe she’ll ask you to watch one with her.
Dan: Well cinema’s always been intended as a communal art. It’s better to watch with another person.
Rufus: She’s a married woman now, kid. It might be time to move on.
Dan: I appreciate the advice, Dad, but I’m just trying to be a good friend. Really. It doesn’t mean anything.

Blair: I will not allow us to go on living like this together. The way I see it, I am mad at you for sending out that video of me and Chuck to Gossip Girl and you are mad at me for running off with Dan, so they cancel each other out. Actually, yours was way worse—I only needed a ride—but the point is—
Serena: Blair, I didn’t release the video to Gossip Girl.
Blair: You took the fall for us?
Serena: It seemed like the right thing to do at the time.

Georgina (Michelle Trachtenberg): What am I going to do? Under my stewardship Gossip Girl is but a shell of her former self. Like AOL or Courtney Love. The only way to remedy this is with a scandal to end all scandals.
Phillip (Nick Cornish): You have a scandal. Dan Humphrey’s the one who sent you that video of Chuck and Blair at Blair’s wedding. And with that to hold over his head you could get Dan to do almost anything.
Georgina: Philip, it’s cute when you pay attention. But if I’m going to load up Dan like a hirsute hand grenade I need everyone to be there when he detonates.

Gossip Girl: Guess what, boys and girls. Looks like school’s back in session. The question is, have you learned your lessons? I hope not. ‘Cause I’m in the mood to see someone fail.

Charlie (Kaylee DeFer): I can’t believe Blair went through with her marriage to Louis. I really thought she was going to end up with Chuck.
Rufus: Yeah, between us I think she may have wanted to. Let’s just say, while love is a very complicated thing, so are pre-nups.

Blair: Step one is accomplished. The thaw has begun.
Dorota: A beautiful Polish spring.

Blair: There’s no way I can bring a royal minder to my ex’s apartment. Looks like you’ll just have to wear a school uniform and play Cupid in my place.
Dorota: Oh no. This is very bad plan.

Gossip Girl: Looks like Gossip Girl just got her first Valentine’s Day gift.

Blair: Why don’t you come with me and my new royal minder to the Cardiac Ball tonight. We can bond over our mutual broken hearts while looking at people with actual broken hearts.

Dan: Blair’s trying to set me up with Serena, which reminded me I didn’t exactly have a great time in high school. So I’m not eager to relive it.
Nate: Before you say no, think about this. There’s gonna be grown women here dressed like school girls.
Dan: I know, I’m sorry. I can’t make it. If it makes you feel any better I will totally sign your yearbook.
Nate: No, it doesn’t.

Blair: I knew there was still something between you. Now, go ask her to Nate’s party. Guitar Hero in one suite, a sushi bar in the other. Girl gets beaned with a Nairtini or someone uses a secret key to sneak into the pool. Just like old times.

Georgina: It says here if Blair defaults on the marriage in any way, the Waldorf family will owe the royals so much money they’ll be bankrupt.
Phillip: And this helps us how?
Georgina: We’re going to show the world what Blair really thinks of her vows. And we’ll use Dan to do it.

Gossip Girl: Look out, B. You may be trying to play Cupid, but all the arrows are pointed right at you.

Blair: Are you gonna make your move or what?

Lola (Ella Rae Peck): Ivy! Ivy! It’s Charlie Rhodes. From Florida. We took that acting class together.
Charlie: Ah… yeah. Charlotte.
Lola: Hi.
Charlie: It’s good to see you. What are you doing here?
Lola: I was about to ask you that same question.

Dan: Georgina. You’re Gossip Girl?
Georgina: What? No. That’s the most ridiculous thing I’ve ever heard.

Blair: I sent Serena to look for you. Am I just setting her up for disappointment?
Dan: Do you really want us to get back together?
Blair: I just want you to be happy. Tell me what would make you happy, Dan.

Gossip Girl: Sorry, S. Looks like your seven minutes in Heaven just turned into seven seconds from Hell.

Georgina: I have something I’d like you to see. {she shows him the kiss photo}. And in your bedroom no less. Has she no decency? Anyway, Happy Valentine’s Day.

Dan: That kiss, it wasn’t like last year. You kissed me back. I felt it.
Blair: It doesn’t matter what you think you felt. Because Serena’s my best friend and I would never do anything to hurt her. I’m sorry if I gave you the wrong impression. Have a Happy Valentine’s Day.

Gossip Girl: I know I promised you all I’d expose a giant secret today and I didn’t deliver. But isn’t that what Valentine’s Day is all about? Hopes dashed, feelings hurt, relationships severed? It’s a day filled with crushing disappointments. Where it’s easy to take advantage of the vulnerable and lonely. While some continue to pine over those great unrequited loves, others can’t help but feel like they somehow got totally screwed.

Charlie: How is she doing? Is she okay?
Nurse: I’m worried there isn’t much time left.

Gossip Girl: And while it’d be nice to believe that most Valentine’s Days end well, we all know they are far more likely to end in heartbreak. XOXO —Gossip Girl.