Vacation. It's great that you're in town, and helping Sam and Dean and staying close when not saving the world. But, I'm in Europe. Who knows what happens next. Have you ever thought about doing something yourself? Like your own vacation.
But, maybe it's about going with the flow. Letting it happen. And, if it doesn't happen, then nobody is hurt. Because you were... seeing it. Like if you fit.
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( Are there other angels he's friends with? )
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I never really thought about it. Things have actually been rather quiet here. The Winchesters are quite busy.
[Getting laid, obviously.]
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( He may not be a virgin, thanks Salvatore school, but his first thoughts are never about getting laid. Good that Dean didn't rub off on him, right? )
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Yes, they were taken care of. At least the ones that intended to attack the school.
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( Why are they so busy? )
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[Yes, that's a nice sanitized "Dad" way of putting things.]
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( This is still Jack, so even sanitizing it like that doesn't quite land either. )
Should I come back home?
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[The brothers are fine for now.]
They're ... pursuing romantic interests.
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( Has he missed Sam and Eileen reconnecting? And, who would Dean be pursuing? He's never seen Dean pursue anyone. )
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[He makes a face because he's not sure how to phrase these things.]
Dean is spending time with Doctor Gilbert, and Sam with a hunter we've been working with.
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( Romantically interested in one another. Right, Dad! )
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I haven't asked, but I would assume so.
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( He hopes. He imagines! )
They should be. And I really like Dr. Gilbert.
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[And more importantly, Dean seems to as well.]
They're ... seeing how things go. Whatever that means.
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( He parses it for clues. )
But, maybe it's about going with the flow. Letting it happen. And, if it doesn't happen, then nobody is hurt. Because you were... seeing it. Like if you fit.
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[He is not well versed enough in these things to know if it's actually effective in practice.]
I just know that they're spending a lot of time together.
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( That seems efficient but not romantic. )
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No, separately. In their individual couples.
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( He gets it! )
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[He hasn't seen them ... actually on a date. It's a very small town. Whatever, it's fine, Jack doesn't need to think too hard about any of that.]
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( LMAO is this the time, Jack? But, his friends are definitely still behind him just -- doing other things. )
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[A pause.]
Shouldn't you be spending time with your friends?
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( That was an easy out, right, Cas? Maybe ignore Dean's text message making fun of Cas' dating habits and why Jack is asking about them. )