However, I do have a trick up my sleeve: an outfit change at work. The great thing about having my own office now [link] is that I no longer have to awkwardly change in the ladies' room. I've been looking for an excuse to break out my $8 Target sale dress and this'll 1) make it kind of a surprise for Dan since I won't be wearing it in the morning and 2) let me wear more comfortable, functional clothes all day before changing right before leaving.
It's not a pink and red cutesy Valentine's Day outfit, but it's a little more subtle, a little more adult and sexy. And it will inherently include a back-up saner version of shoes from the day outfit in case this unplanned evening ends up including any walking. It's not worth the torture of trying to walk in heels.