[He's not sure if he should drink to any of that or not. God knows he hurt people back home, Jack included. Sometimes it was deliberate. And maybe hurting Spike wasn't the goal with restoring his soul but they knew what they were doing. They knew there would be consequences. He gives up on his coffee. There's too much moral ambiguity in his life for this game, particularly when it comes to relationships.]
So why are you so nervous about this thing with Chekov? It's not something you're doing to hurt anyone and you care about him, you've said it before. Why just assume this will be a bad thing or that it's destined to end badly?