Generally Bucky doesn’t really do dates. But first dates yield no real pressure and it’s been a long time since he’s had a good night out.
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On principal Tony doesn’t do dates because they’re mostly a waste of his time and efforts. Since taking Peter in two years ago his life as been a bit of a mess trying to figure out how to raise a teenager who has lost so many people that are close to him and, on top of all that, is trans. That coupled with his regular work schedule hadn't left him a lot of time for a relationship.
Tony doesn’t want what everyone else seems to want, and can’t make himself like what everyone else seems to love. So he keeps his mouth shut and his smile bright.
It doesn’t occur to him that maybe his normal is not to be.
The vigilante Iron Man is in the habit of showing up at a fight and disappearing again when it's done, whether the Avengers want his help or not. Steve has had more than enough of it, which is why, when Bucky finally manages to get him with a tracker before he flies off, Steve isn't going to let little things like a broken leg, an overprotective boyfriend, and a mysterious satellite deadzone get in the way of tracking him down.
Their - okay, fine, Steve's - truck breaking down on them might be a bit more of an obstacle, but at least the mechanic they've found, a guy called Tony, is nice enough to put them up - or should that be put up with them? - for a few nights while he works on repairing it.