Yeah, that definitely sounds like some serious overkill. Questions should stimulate conversation, not be the entirety of the conversation. Constantly asking someone if they’re uncomfortable or if something is wrong is not a good idea either.

The last person I met up with asked SO many personal questions, about how I was feeling, was I uncomfortable, did I think I did something wrong, what it was I was looking for, how much space I wanted, etc. etc. etc. that I was VERY uncomfortable and felt like I was out with a shrink rather than potential lover. That…

I had the rule of twos for a first date: Two people, two hours, two in the afternoon, two bucks. Avoiding a group date situation gives you the opportunity to get to know the other person better. As you note, a short date takes the pressure off both people. An early afternoon date on the weekend also takes the pressure…