If there was one thing that Tony Stark did right every time, it was his skill for throwing some of the best parties that New York had ever seen, and this night was no exception. He had made a small fortune on the sale of the tower, and had donated every cent towards the building of a free-service hospital for a very deserving neighborhood not too far away. If he was going to celebrate the accomplishment and the realization of another of his projects, then the entire city was going to be up late tonight celebrating it with him. The building was emptied for the move to the compound upstate, so he took full advantage of the extra space, stocking bars full on several floors, with lounges and dance floors open on each of them. He had invited everyone he knew, and quite a few people that he had never even met, just to be sure that the building was retired from the Avengers' service with a bang.

"I'm surprised that the police haven't stopped by yet," Rhodey nudged his friend with a gentle elbow to his ribs. "You've outdone yourself this time, Tone."

"What? I can't hear you?" Tony yelled, despite there being no more than a foot between them.

"I think you just made my point!"

Tony gave him a thumbs-up and a wide grin, hoping that whatever it was that Rhodey had said was answered with the generic gesture. He looked around the room to spot each of his teammates, only to find himself disappointed at the bored and annoyed looking Steve, sitting with an equally unamused Bucky at his side at the bar with long-since finished drinks in their hands. When the two men stood and appeared to be making to leave, Tony excused himself from his friend and hurried to intercept them.

"Hey! Nuh-uh! Sit your asses back down!" he warned as he approached. "You're not leaving yet! We're just getting started!"

"Tony, we've been here for three hours," Steve argued with a long sigh, "it's started and finished." He set his empty glass on the bar top, first wiping away the condensation on its bottom because he did have good manners, after all, giving Bucky a nod to leave when he stopped and gave Tony his full attention once more. "Hey, you look kinda pale. You okay?"

"I'm goo...I'm good..." Tony stammered, wobbling on his feet. "Not for you...to w-worry your pretty head about..."

"Told ya he thinks you're pretty," Bucky laughed, but it was quieted immediately when he saw Stark's eyes roll back just slightly and he began to fall. "Whoa, shit!" he called out, barely getting a hand on Tony before his head could bounce on the hard wood floor. "What the hell?"

Tony continued to mutter something unintelligible under his breath, despite his wavering consciousness, his eyes closed and his body limp. Steve assessed the man quickly, counting his breaths and giving him a firm shake to try to wake him, only to laugh at his own attempt and the futility of what he was trying to do. "Yep, he's had one too many. Come on, let's get him up to his room."

Even from the other side of the vast room, you had caught a glimpse of what had happened, your attention drawn when you saw Tony's head disappear from sight as he fell to the floor. Pushing through the throngs of people, you forced your way across the group as quickly as you could, trying to get to the trio before Steve had a chance to get Tony away from the crowd. "Steve, wait!" you called out over the deafening music, thankful for his enhanced hearing.

"Hey, (Y/N)," he greeted, Stark in his arms, "haven't seen you all night. Let me just bring him up to his room and I'll be right back."

"Actually, about that," you smirked, "wasn't there something you said not long ago about never being able to prank this guy? Now might be your chance."

Steve looked to Bucky, who was clearly intrigued as he nodded along with your realization and idea; it was true that Tony had done his share of pranks against the duo over the years together in this building, and perhaps it was a fitting way to say goodbye to it. Maybe it was perfect karmic intervention that it would be Steve who had been there when he passed out, and to just ignore the clear signs would be a disservice to fate.

"What did you have in mind, doll?"

~~~

The next morning, a blaring alarm and the burning beams of sunlight through his curtains left Tony growling and pained after his night of debauchery, but the early morning meeting that he was stupid enough to set up couldn't be missed. The curses continued when he swung his heavily fatigued legs over the side of the bed and his feet landed uncertainly on the floor. He berated his pants for going on inside out, and he chastised his socks for not matching. Tony didn't usually suffer from a hangover, so the sensation of his head being crushed until his eyes popped out was entirely new to him. Rather than allowing himself to drive, given his need to keep his eyes tightly shut and the likelihood that it would impede his skill, he had FRIDAY guide him to work at Stark Industries.

As if by a divine miracle, when Tony dropped into his chair in the main conference room, the lights were already dimmed and the presentation had just begun. Pepper was an angel, he deduced quickly, hearing his own words being said back to him rather than having to say them himself. He likely wouldn't make much sense right now anyway. Leaning back into the chair with a quiet moan, he removed his sunglasses and tried to find his concentration.

But just as his glasses landed on the table top, her voice stopped.

"Something wrong, Miss Potts?" one of the other nameless suits in the room asked.

"Tony?" she asked hesitantly. Her eyes were squinted, trying to see him through the darkness of the room.

"Hmm?"

"Are you..." she paused, her focus still tight as she took a few steps around the table. Her eyes never left him as she moved, and Tony never looked away, even as his fear grew with each step. "Are you...wearing makeup?"

"No!" he scoffed immediately. "Why in the hell...would I...wear..." he too stopped, his foggy mind screaming at him to quiet his embarrassment. "Wait, how did I get up to my room last night?" he asked, more to himself. "The last thing I remember...(Y/N) and Steve...and Barnes..."

"I think that might be your answer, Tony," Pepper laughed, though it stifled quickly when she remembered her surroundings. "Go ahead and clean that off. We can hold until you get back."

"Okay, yeah...thanks," he answered, but his mind was still trying to put the fragmented pieces of the last evening together. Tony decided that it wasn't much of a point in trying when he felt this terrible, and when he may have actually still been a bit drunk, now that he stopped to consider it. "Hey, Pep, tell me one thing."

"What's that?"

"How do I look?"