Going to give a bit of my history, where I have been, where I am, and where I plan on going.

I am over 40 years old. I never have been good with women. If not for women approaching and being the man so to speak, I would still be a virgin. No lie.

I was a virgin until I was 18 or 19. A coworker that was staying with my roommates and I told me at work one day she liked me and I could come sleep in her bed if I wanted. It was about two months before we had sex. That did not last long and she was gone.

When I was 21 my best friends sister became interested. I had the poor girl so confused, when she offered to come to my house and wake me up I told her I would leave the door unlocked. She later said she did not come over because she did not know if I was serious. She finally got me in bed one night, I must say I made her work hard to accomplish that goal. Not sure what I was thinking. Wound up getting married to her, lasted about 15 years. Left her four or five years ago.

Since that time have been with one other woman. A prostitute, we met on the street, and what a surprise, she was direct with me. I did not pay, I realized she wanted me enough I could control that situation. If I can have sex with a prostitute for free, I should be able to get other women...

Had a good female friend from the time I left my wife. If you cannot tell I was deep in the friend zone with her from the above, you may need more help than I do.

So what was my deal, why has it been like this for me? I did not want to be rejected. I now know how stupid that has been. I finally decided to man up, and face it head on. Knowing I was going to cost myself a friendship, and be rejected both, went for it. Got shot down, and while I do miss the friendship, the rejection I did not feel a thing. Over 40 years, and I have missed out so much due to a fear that did not cause any feeling at all.

Many may look at being stuck in the friend zone for years as a horrible place to be. I felt like that myself the entire time. However that is what it took for me to decide I had to do something. Here is this girl, that would do anything for me, except have sex. She took me to all different kinds of places, some very expensive. Took me out to eat all the time. Gave me money just so I would have some. I call needing something, I had it. I call wanting help with something, she was there. What she decided over the years she wanted in a man fit me perfectly. Right now, she is out there looking for a guy just like me, just not me, litterally. We would argue and she was fine, and she once cried thinking she would never see me again. All of that, and the one thing that was unacceptable to her was me asking her out.

I should not had blown the friendship in retrospect. However I knew my fear of rejection was killing me. I was at the point I decided being rejected by her would be far worse than being rejected by anyone else. I felt nothing negative when it happened. I was happy and relieved to be honest. It felt great, at least I had tried. That felt wayyyyy better than doing nothing.

I have other issues I need to deal with, but I am going to get through them. I have always been shy when first meeting people. Once people get to know me the majority think I am great, fun, smart etc. Now to get sexy and attractive into that mix.

Guys, if I can do and get through this, anyone can. I am shy, short, no teeth (drugs got them a long time ago), no job, old, no car, broke, and live with my brother right now. I will be starting a job in a few weeks, so that will take care of the no job, living arrangements, car, and hopefully sooner rather than later the no teeth.

Yes, I have nothing going for me in all of those areas, I am diving in anyway. People still think I am a great guy without those things. What can she say, no? Fine, she is going to have to say no.

My next biggest hurdle is breaking my shyness. I know I still look good. I have various women tell me I look good, and I keep on going. I have had several ask if they could go with me, when I was walking down the street, and young girls decide to start following me around when they approach and start talking to me. Several in nightclubs have made the guys in thier friend zone by my drinks. I had one girl I knew a while back offer to fly me accross the country to hook up with her, she was very clear that is why she wanted me to come, and I screwed around and blew that off as well. Yes, I have been a idiot many times when I had to do nothing to get some except to take it. I have good eye contact and body language. I do not open my mouth or push boundries when I should be, or know the boundries go much farther than I go. It is not a matter of thinking bad about myself or whatever, just not taking oppertunities when they present themselves to me. One specifically I need to ask about.

My sister in laws mother (same age as me), I could go to her house right now, and do what I wanted with her I am sure. Several issues. She is not normally my type, however the hornier you get, the less choosier you get. She is my sister in laws mother, not too sure I want to open that can of worms up. She is fine with casual sex, I would not want it getting out we had been or was sleeping together and almost positive my sister in law would be told, if not everyone. It is me not wanting it to get out, my sister in law has asked me about getting with her mother several times and tried to encourage me to do so when I first met her, and my brother could care less, so it is me not anyone else that would have a problem with it. Her mother has issues I would not tolerate being in a relationship with so that is out of the question. I have no doubt casual sex would not be a issue with her. She could not stand it when she had come over, and my wife (not yet divorced, this year I will be) came with my son to spend some time at my house. Her constant remarks about me being her boyfriend in front of both of our families, and in front of her boyfriends when she has one, does get on my nerves at times. WHen she knows I am interested in someone else she playfully but seriously lets me know she is jealous. So should I go ahead and have some fun with her, making it clear that is all it would be? She is single right now.

My next obstacle is my shyness. Approaching itself would not be a problem, opening my mouth and saying something is. This issue is not specific to women or young girls. I have the problem with any stranger, male or female. A few months ago I did the mission of asking the time. I have not done any work towards progressing other than that one time. That day I was a idiot as well. About the only people I did not ask the time was the women I had good eye contact with, and seemed they would not had minded me approaching them. Good job, avoid the ones that looked like they would be interested lol.

Once I know someone a little bit, the shyness goes away, although I am still quite. I am up for suggestions on how to deal with this aspect. Right now I think going out and getting peoples attention, getting them to stop, and talking for at least a few minutes would help. I still wont know what to say, I figure saying something and making a fool out of myself would be better than nothing to get some practice.

Help me get to talking to random strangers. I am open to anything right now, I am at the point something is better than nothing, if for only experience to learn from my mistakes.