Oh my god, I love this!
You're fun and creative, your boyfriend is a game player, and I can't WAIT to see the outcomes of this.
I think the ballet flat options you've posted up there are pretty good if you're going for pink and girly. The heels... well, that all depends on what kind of heel you wear most often. To me, a heel like that is pretty unwalkable, but then again, I wear heels so rarely that my muscles just don't do it.
I'd look for heels that are similar to what you'd typically wear walking around. And maybe pick a style with a cloth upper or a soft leather that'll stretch easily around his feet, which are probably wider than women's shoe design is meant for.
And please please do report back when the outcome of the bet is decided.
What does the winner get? Or perhaps it's something you'd rather not say in a public forum.
