In all fairness, Shego, Kirk had had very little to drink in the year and a half that he'd been a starship captain. Only ever on shore leave and even then, he didn't let himself get totally smashed. In case of emergencies where he'd be needed. So while he was probably still a lot better at drinking than her, he wouldn't really be able to tank it.

He probably wouldn't even try to draw on her face either.

Kirk smirked somewhat at that and nodded as he got up to go get his set of glasses and some whiskey. Because that was all he had. "What do you want to drink to?"