4x01 - Blair spends her summer getting “lost in a daydream” in front of her favorite painting.
4x22 - Dan “paints” Blair in his book.

( + some geekery about this parallel )

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Vanessa: I think we should just throw down and see what happens. If we go up in flames …
Dan: at least we know we burned trying. 
Vanessa: I’m scared. *Dan kisses Vanessa*

Chuck: In our life we can’t have everything. Anne won’t be the only person who might think you’re weak for forgiving me. 
Blair: And you won’t build a business based on being New York’s bad boy bachelor. 
Chuck: I understand the consequences. Are we willing to pay them? 
Blair: Serena, what are you doing? 
Chuck: I say we go up in flames together?

Dan: Vanessa, I know we’ve been friends since we were little, and we both like pierogies, and my dad really misses you, but just to be clear, so there’s no misunderstanding down the road, we are not friends anymore.

Blair: I thought, after everything you went through—Prague, Eva, Russell—that maybe you’d changed. Who was I kidding?
Chuck: Don’t say that. 
Blair: You have years before you’re capable of a real relationship. If you ever will be. I’m sorry Chuck.

Dan: Care for a dance?
Blair: I guess.

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302 - The Freshmen
419 - Petty in Pink

Pacey: Wanna know something, Miss Josephine Potter? I think the world may just surprise you yet. I mean, you fall in love, it doesn’t work out and you think that it’ll never happen again. But it does. Believe me, it does. In the strangest of places.

Dawson’s Creak - S3E13

Dan: Blair, your prince is out there waiting for you. Might not be me or Chuck, but he’s out there.

Gossip Girl - S4E18

1x18 DAN: This is so weird, I don't normally do plots against people.

4x20 DAN: It sounds like you learned your first lesson in being an Upper East Sider. It's time for your second lesson: face your enemies.

The student has become the master. Sort of. Like, if you squint and ignore the fact Charlie is actually another Georgina. Hey, there're two more seasons! Probably.

Credit: whiteotter spotted this parallel.

The dress Blair wears the first time she kisses Dan (4x17) is one of the dresses we see in the Paris shopping porn montage while Blair and Serena are shopping for her date with Prince Louis (4x01).

Rochellena from FanForum noticed this parallel:

In 4.01 they do a montage of a bunch of Paris stores, one of the few times they actually focus on a dress for 2 seconds instead of just one is when they are showing the dress that Blair later wears in the first kiss scene. I thought it was kind of interesting with all the speculation about parallels and hints from the first episode.

3x19 vs. 4x19

Blair has a cunning plan. It involves kissing. Dan is not impressed. It doesn't go as planned.

3x18: "You deserve to be with someone who makes you happy."
4x18: "Your prince is out there waiting for you."

And Chuck and Serena are in the frame over Dan's shoulder in both scenes. MAKE OF IT WHAT YOU WILL.