“I need to be casual but not too casual. Dressy but not too dressy. I need him to think I just threw on the first thing I found and that I'm not taking this too seriously or overthinking it or even that I was thinking about it at all. Because I'm not. I'm totally not thinking about him, and I don't want him to think I was thinking about him, but I don't want him to think that I'm not thinking about him, because clearly he thought about me enough to ask me out and it would be mean not to be thinking about him at all, so I need just the right amount of thinking, and I'm not sure if that means boots and a skirt or skinny jeans and ballet flats. Help!”