The new girl had no date for prom, so I'm going to have the old hobo step in.
I don't care for this idea. Why would you set her up with a hobo?
She is very upset now and that made my day.
That is going to make her prom really awkward. You should do things that make it better not worse for her.
Why? I get off on this.
Think about how you would feel if someone set you up with an old person. Do you really want to make people feel embarrassed like that?