OP
1) You think too much! Your higher level brain functions are overriding your lower level brain functions that responsible for successful physical actions. Stop thinking! You job is to get a date and see if the hormones kick in. Your very smart brain is killing the hormones on both sides of the table. The physical is low level autopilot stiff. Let it go! Let it do it's job!
2) You care way too much. I just came out of a relationship with a crazy BPD girl and now attractive normal woman seem so boring. I do some online dating right now. One very attractive girl is 10 years younger than me. I decided after the 1st date I wasn't going to see her again. Too many issues, not a citizen, could move back to Argentina any moment, has a 4-year-old daughter. But she keeps texting me and let's me know she wants to go out with me. So I date her. She's very attractive. Every date I act like it will be the last, which seems to make her more attracted to me. I have another woman 4 years younger than me that when I told her I was too busy, told me she hoped we would go out soon. She is georgous, but I don't care and that makes these woman more interested. Stop caring.
Get a date, if after 1 to 3 dates, nothing happens move on. You are wasting your valuable resources with this one.