Shy and lonely. Please help.

I was trying to write a great big bio to give background to my problem but it wouldn't fit on my profile

In summary, I have occasionally crossdressed all my life (am now 40), usually at times of stress or when I've felt lonely. About a year ago, as I approached 40 it finally hit me that I'm a 40 year old virgin whose shy and lonely. I tried a dating site, exchanged one or two emails with prospective dates and then put a photo on the site. Never heard from anyone again. I know I'm not attractive, but didn't realise (or was in denial) that it was that bad. I'm short, overweight (not obese, just carrying a few extra pounds) and socially inexperienced. Never had a date and have few friends.

The cross dressing has become a daily, permanent state. I suspect that the feelings of loneliness are being expressed in the cross dressing. I think I'm craving female company but lack the confidence or knowledge to know what to do about it. I've always been attracted to women but guess I don't really know what my sexuality is, having never even kissed, dated or even held a hand. I'm not too worried if I turn out to be gay or a transsexual (or whatever the correct term is) as long as I know and can find happiness in myself as I don't think I really know who I am.

Can anyone suggest anything that would help me overcome shyness and a chronic lack of confidence in social situations, or a way in which I can find out who I really am?

Hi, Astenon. I found the internet dating to be kind of cold. You end up posting a pic and answering questions about your height and weight and things that seem pretty superficial. All i can say is have you ever met a drop dead gorgeous person but they are mean as can be abd start looking ugly? And my favorite high school boyfriend was covered in acne, but he was so smart and everybody loved him. He always stopped to give people walking to or from school a ride. Also most people when they found out out i lived with my 21 year old sister thought it was cool and asked if she bought me alcohol. Jeff said he was close to his older sister too and never asked stupid questions . I propably, seriously would have married him, but he died in a plane crash with his parents. So the moral of the story is your inner beauty shows on the outside when people get to know you, and you don't want a shallow person that is only interested in the surface anyway. Also, thanks for reminding me there are decent guys out there. Ps. As far as the cross dressing and sexual orientation, whoever you are, what makes you happy is ok and it may take time to figure that out.

I think you need a therapist whom you would task with something very specific, ie social skills training.

Overweight is a very common conditions nowadays. In both men and women.

Being short when you are a man does put you at a disadvantage, agreed. Short women can. Be called petite and fragile and delicate, but our language lacks words to admire short guys with. Very unfair.

Thanks so much for your kind words. We nice guys do exist. I just hope I don't magically turn into an *** if I do meet someone.

I think I need to find an interest or something that's going to get me out there, but have trouble thinking what that could be. My interests tend to be nerdy (computer and role-playing games) and there's not many women that have the same interests. In the interest of at least getting out of the house, I've found a local RPG group. All I need to do next month is try to pluck up the courage to actually go!

Some people spend their lives in pubs - I just find them intimidating. Still, nothing ventured, nothing gained as they say.

I am a woman and went out on a date with a very short guy a little over a year ago. He was the same height as me (5'4") and it didn't make a difference to me because I liked him anyway and thought he was nice looking. However, he never contacted me again.

Maybe it is because you thought that he was nice looking. Thought to yourself. Maybe had you told him, the outcome would have been different. I am not saying you did anything wrong and I would have done exactly the same thing in your shoes. I am just saying - perhaps he needed a little boost to his self-esteem to keep going.