Thank you for writing. I can’t respond to everything in your email but let me offer a few thoughts:
First, regarding your difficulties with women: Please don’t be so hard on yourself. Your problem with interacting with women is not unusual, even if you think so. You didn’t have a positive role model of manhood from your father, so you didn’t learn how to relate to women in a respectful and loving way from him.
Social skills are learned. They are not in-born. You need a safe place to learn them and to get some practice. I have a number of suggestions:
First, get involved in some kind of activity that includes single women your age. When people focus on an activity (a charity, a sport, a building project), they get to know each other gradually over time. It takes the anxiety level down since the focus is on the activity, not on each other.
Watch chick flicks. Yes, watch movies and study them as carefully as you studied for exams. Although the romances are idealized, they will give you some idea of how to relate. It’s like learning a new language. Memorizing those dialogues our teachers made us learn provided a template for interaction.
Individual therapy with a female counselor may also help. Like the group. it provides a safe place to ask your questions and to get feedback.
Finally, consider joining an online forum here at PsychCentral. You can get good advice and support from the members.
Do not get involved with prostitutes as a sad substitution. Such encounters are not a model for normal relationships with women. They may give you an outlet for sexual frustration but they will damage your ability to relate to the women you want to be with.
Regarding your work issues: A couple of times you said you “used to be a nerd” as if being a nerd is a bad thing. It’s not if it is defined as being intensely interested in mechanics or sciences. If you were seeing me for therapy, I would want to explore with you why you gave that up since you did well in your exams and in obtaining your first job. I really think it would be useful for you to talk to a therapist about what happened that made you become so discouraged.
I wish you well.