What if my date shows up wearing something embarrassing?
You want to see what your date, and this goes for the guy and girl, you want to find out what they're wearing before hand. Maybe more for the girl. If you think this is a guy that maybe needs a little bit of help in the styling department, help him out. He might need it, but he might not know how to ask. You might want to poke him a month before or two weeks before and say, "Did you set up a hair appointment, are you going to get your hair fixed? Do you have your suit or tuxedo? What's going on there? Just take a look and help him out if you think he needs help.