It's not so much a win that he's after, not over her, anyway. The whole idea of having an anniversary in the first place is still weird and novel, and honestly doesn't feel quite real. These things happen to other people, but not Jim Kirk. Except, apparently, when it does. He's still trying to wrap his head around that a bit.

He smiles and flashes her a thumbs up before she disappears into the rows upon rows of shapewear, and turns his attention towards actually finding something that'll look good on him. There's a lot of comedic options available, but he ignores them all, narrowing his search to the more serious choices. Something in black, to match the rest of the ensemble... hmm. Yeah, this one'll do. Not his usual kinda thing, but it's not really for him, now is it?

There's a dumb smile threatening to break out on his face as he collects his chosen purchases and heads for the dressing rooms to make sure it all fits right. The thigh-highs and whatnot are easy, but the corset... that's new territory. So many laces to snug up. "Am I doing this right?" Seems like she'd definitely know if he's wearing it stupidly wrong.