Pfft, don't worry about that. You could always go with the Marlene Dietrich look. [Giving her a onceover, with an oh-so-arch raise of the eyebrow.] That you could pull off, too.

[He reclaims the fedora and sets it in his own lap, fiddling with the hatband.] Well, you're right that this is still pretty classy compared to some of our other dates. I know our first go at being all fancy-fancy ended badly, but if you want to try again -- I'd be up for that.

Just don't expect me to buy a new outfit every time, okay? I have a lot of mouths to feed, and they're all teenagers in that "bottomless pit" stage.