Help, I want to date but having trouble taking the leap

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Hello, I would like to date but I'm having trouble getting started. I'm a male & 42 years old. I've been on 5 dates ( 3 "first" dates & 2 "second" dates). I've had one date set up for me & I went out with her on 1 "second" date. I had 2 "first" dates through online dating & had 1 "second" date from those 2 "first" dates. It's hard for me to just go up to a woman & start up a conversation ( I have trouble starting conversations with males, too). I'm afraid to start relationships (romantic or friendly) because whenever any of my relationships starts getting deep, the relationship usually ends (I only have 1 person that I'm really close with) with the other person either going away or we just fade away from each other. Also, there was this girl I knew in high school, she was in my English class (I knew her for only 1 class / 1 semester), I never seen her outside of that class. We hit it off instantly, I have never felt as comfortable around another person. I have never forgotten her, I think I fell in love her, but back then I wasn't interested in dating. But, I've always hoped that she would come back into life some day, so that stopped me from dating.

What I would like help with is 3 things.

1: I would like to learn how to get close to people without worrying if the relationship will end.

2: I would like to know how to tell if a woman is interested in me by just looking at her, so I can know before I go talk to her.

3: What is a good all around conversation starter for a man interested in a woman for dating.

Thanx & I hope somebody can help me.

How about looking her up on facebook?

I got some anxiety pills from the doctor. I will see if this will help me. Usually when I try to approach a woman I'm hyper ventilating and sweat runs down my back like a waterfall. I'm grasping for words and my face turns red. I get so overwhelmed that I can't think on my feet when she obviously realises my position and/or intention.

I checked she's not on Facebook.