leighton won, they obviously made a mistake.
So here's what I'm thinking...Chuck and Blair are broken up, but she finds out she's pregnant with his baby...not Jack's. And maybe the proposal part is Chuck popping the question because of the pregnancy, but I highly doubt they'd get engaged...maybe just end up talking about it and acknowledging that it will happen in the future. But if Blair gets pregnant, my guess is that she looses the baby.
I agree with gossip girl bitch, the video clip they're showing is most likely a dream sequence. But I'm also thinking it's possible that Chuck knows that Blair is planning on sleeping with Jack and is okay with it. Maybe Blair freaks out at the last second and tries to stop him, but Jack does have a history of attacking women. And it's not like Josh Schwartz and Stephanie Savage are against recycling some of the plot (the whole Jenny rebellion thing).
Regardless, I'm pretty sure that whatever happens in this episode will be what breaks Chuck and Blair up.
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