If you guys have a great time, you're both left wanting more." —Greg G." /"Please don't assume we're going to the nicest restaurant in the city because I won't take you there. Opt for something that gives you both an easy out, like lunch or a drink.
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Dainty foods (read: salads) seem to have a low correlation to fun and enjoyment.
First few dates, make the food good, simple and completely forgettable so you can focus on each other." —Max S.
Invite your guy and his crew to hang in a big group.
That way you can get a feel for what he's normally like around his buddies and it'll let you both relax a bit more.
If we end up grabbing drinks later and a woman insists on paying, I really like that a lot.