I'm an old man, maybe that's why all the dating stuff seems so weird.
My idea of "dating" was (am married now) to spend as much time together as possible, because if you were in the running for partner then: (1) I preferred being with you to being alone or others, (2) I wanted to learn as much about you as I could to decide if this would work, and (3) it was time to get past the awkward phase so we could start having sex (something that was at a premium because I've always been a "one woman guy" so it only happened with one person at a time who was expected to return the favor.)
I think I'm glad I'm not single. Does it really have to be this hard?