I can totally understand that need for wanting to know, "where is this going?"
What I used to do, in the days before I got married, to take the pressure off, was to make dating a game, or a learning exercise.
I just set for myself the goal of having an enjoyable date. My focus was all about enjoying the company of another person, and to find out what was most interesting about them. At the most, the biggest decision I had to make was wheteher or not I wanted another date with them, or another chance to get to know them. It helps so much to reframe things for oneself, and to take a different position, which offers a new perspective. Let go of expectations about "making it work," is he "relationship material," blablabla. So what if he isn't? You can still enjoy the pleasure of someone's company and companionship, and have someone to do fun things with.
I dislike the idea of a date being an interview process to see if someone "qualifies" for more emotional investment. If you can relax a bit and not think too far ahead, you can have a really good time dating. Then, if something substantial develops, it happens of its own accord. It just takes some self-awareness to catch yourself when you start worrying about "where is this going," to nip it in the bud and let go of that train of thought.
Hot chick in the city.
Oh, oh, can't you see? Love is the drug for me.