Something I stumbled on: My worst date ever. A fairly bad date, but if that's his worst, I won't worry about him too much.
My best first date was a blind date. (Future) hubbie picks me up and takes me sledding at night in New Hampshire. 12 degrees (F). Had his toboggan tied to the roof of his old wreck of a Jeep, and a six-pack of beer on the back seat. You just had to like the guy. Tall, dark and handsome too, with plenty of interesting quirks.
I guess it was a test of my gumption, but, to his credit, the toboggan on the steep hill made me end up holding on tight to him - a total stranger (well, with the introduction by a close family friend). But it did feel pretty good.
Only the beer was wrong. For nightime sledding, brandy is the thing, but he was a poor student at HBS at the time.