"Uhm, shoes, I guess?" Shrugging, he stays just about close enough that it's obvious he won't suddenly bail out, and far enough away that it'd be difficult to grab his hand. "If that's alright."

In a way getting shoes first means getting the possibly easiest part out of the way. He can't see Jade letting him wear anything too casual anywhere on his body, but with shoes that's not so bad. Start with something that isn't so bad, get used to whatever Jade's going to throw at him.

Somehow survive this trip without starting a fight.