get of caps lock?

Hire a sitter and go. Have a fine time. Since it's a school night, be home in time to get the sitter home at a reasonable hour, if s/he has to go to school tomorrow.

I can imagine it will be very awkward but i would pick a social senrio where conversation is already supplied.

Example: An art exhibition, you have the art to talk about etc.

I'll be your friend :)