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.
*
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.
Sleep-deprived and under-caffeinated, grad student Tony falls asleep in a conveniently empty classroom and wakes up in the middle of Bruce’s Physics 101 course. After seeing a groggy Tony fumble a simple question, actual-student Bucky offers to tutor him. In a moment of “oh no; he’s cute” panic, Tony takes him up on it. Now, in addition to his already complicated life, Tony has to figure out the answer to the incredibly messy question: “How do you look like you’re failing the class, when you literally wrote the book?”
In which officially Bucky and Iron Man are dating, unofficially Bucky knows Tony is Iron Man, officially no one else knows Tony is Iron Man, and unofficially Tony and Bucky are trolls.
Or, Steve and Natasha learn never to assume they know what's going on in Tony and Bucky's relationship.
“What,” Tony says softly but with a great depth of feeling, “the actual fuck just happened?”
“I believe, Sir,” JARVIS pipes up from the phone in his pocket, an unnecessary amount of what sounds like glee in his voice, “that you’ve once again managed to maintain your closely guarded secret identity. Truly your subterfuge skills know no bounds."
“You’re an asshole J,” Tony mutters back as he reaches up to rub at his temple. He either has a headache coming on or a blood clot. At this point he’s honestly not sure which he’d prefer.
"I did learn from the best, Sir,” JARVIS tells him sunnily.
"I’m sure if there is anything to find, I’ll find it. I found you, didn’t I?” “I’d say Iron Man’s the one who really found me, but you’re the man behind the machine, right?” The way that was phrased, it almost sounded like James knew—no, that was impossible. If the rest of his teammates, who had all known both Iron Man and Tony for ages, couldn’t figure it out, how could James have figured it out so quickly? Tony was just being paranoid.
--
In which Tony's managed to keep the fact that he's Iron Man a secret from his teammates and the rest of the world for years. With that kind of track record, fooling Bucky should be easy. But Bucky isn't the Winter Soldier for nothing.