Blair sat up in bed, staring at him in disbelief. One perfectly-plucked eyebrow was arched. "That's your worst fear? Seriously?"

"Hey," Dan chided. "You said no judgment."

"Please. I'm Blair Waldorf. You're Dan Humphrey. Judging is what we do."

"I don't see how my fear of you running back to Chuck is any worse than your fear I am going to randomly have sex with Serena at a hotel bar."

"It's not the scenario itself, so much as the way you described it. You're such a writer. So much dramatic flair. I stand you up, run to the roof of the Empire where Chuck treats me like crap again, then I follow him to a casino in Monaco. I am pretty sure I am banned from the principality of Monaco."

"Yeah, well, I am pretty sure real people don't have divorce parties, so it would very difficult for me and Serena to reenact the Nate-and-Serena Shepherd-wedding debacle. "

"And it's so realistic that I would bet my fortune on a hand of blackjack? First, why on earth would Jack and Chuck be trying to gamble their way back into Bass Industries? Second, why would betting all my money on a hand of blackjack, which is a game of chance, count as betting on Chuck? It doesn't even make sense."

"Okay. Point taken. But your scenario was just as ridiculous. I am not interested in Serena. I haven't been for a long time. I wouldn't have sex with her just because I gave you an ultimatum and you stood me up. It's not Chuck-and-Jenny part two. Serena already told me she was in love with me. Several times. And I mostly ignored her. Much like you have ignored me every time I have said it to you. Except then you concocted this weird worst-case scenario game. Also, I love how your worst-case scenario is more about Serena than me, with her leaving again and getting all drugged up and mauled. Come on, she's grown up and matured. And so have we."

"I think it was a brilliant exercise. Now we realize we are both ridiculously insecure people with overactive imaginations. We can proceed accordingly. Handle with care. Avoid divorce parties and exes and dramatic scenes on the roof of the Empire. Cause here's the bottom line, Humphrey. You're my best friend. You bring out the best version of me. And I could love you someday. If you cut your hair. Which you're going to have to do during August in Italy."

"We'll see. Now get up. We need to get dressed or we're going to miss our flight."