What to wear
If you want your date to know that you don’t get out a lot, I recommend a CS50 shirt. If you want your date to know that you’re shallow, don a HCCG Patagonia. If you want your date to know that you’re in a final club, go all out with that Vineyard Vines vest and a baby blue polo. I’m kidding (only a little bit, though). Dress casually but not sloppily. Athletic shorts and a stained t-shirt are out of the picture, but a mildly nice button down and jeans or that sherpa jacket you haven’t broken out yet is a solid move. Maybe wear an accessory as a conversation starter or just to show that you put some effort into this and totally didn’t do Datamatch because your blockmates are worried about your love life. Deodorize (please) and brush your teeth. It’s not a job interview, but it is a form of coerced social interaction that should be approached in a mildly respectable fashion.
Where to go
Anywhere but Clover. It’s not even an option this year. This is just a suggestion regardless of whether or not you’re doing Datamatch. Next.
What to talk about
Start out by making a banal joke about how zany the questions on the survey were. It’s a layup and shows that you know how to read. Talk about your extracurriculars, hometown, where the bodies are hidden, favorite bands and movies, etc. Let your date talk, though; after all, it’s a “date.” Try to not think about the fact that the person is likely sitting across from you because free food was involved. Be calm and listen.
How to follow up if the date goes well
Ask for their phone number and say “you’d love to get a real meal sometime” and then chuckle, noting that you “mean it.” I don’t know what the relationship retention rate is for Datamatch, but I’m sure it’s not 0 percent. College is about putting yourself out there and shooting your shot. Maybe you did well on this date and can make something work in the future. There are friends and lovers and LinkedIn matches to be made, and this is your chance to do all three.
So, that’s just about it. Good luck. Meeting strangers is hard, but being alone with your thoughts is harder.