How about this cap?
Are you planning on wearing it 24/7 for the rest of your life? It's got to come off at some point, especially if-- as you alluded -- you don't want to die a virgin.
You are right, that's why I don't feel any boost of confidence when wearing a cap, I know I'm hiding something ugly. But when I did shave last year I was thinking how isn't this a way of concealment also?
I can at times grow confidence and go and approach girls by not obsessing about my hairloss. But the confidence is always like a spike that goes down after a few rejections and my belief is that the rejections are due to my baldness and/or my faked confidence.
I live in Bangalore, a very urban part of India. There is no dearth of good looking guys with a head full of hair, I rarely see younger guys with extensive baldness as mine. Shaved heads are never seen. Only one guy did I see in a bar with a shaved head, and I'm not sure he is balding or not. He was extremely confident and dancing with his gf.
The thing is that perhaps (and its only just a perhaps) the rejections you're getting is because your approaching baldness is knocking a major hole in your self confidence. Its possible that the rejections are partially because of your low self-confidence, rather than because of your hair itself. Living in Bangalore, you can easily get away with having a shiny head

Its a very progressive and modern city since the IT and telemarketing businesses moved in, so going bald would just make you look like one of the hip and trendy guys, even if its a hipness and trendiness that you've created

You dont need to conform with the masses to make an impression. Sometimes, being an individual can make much more a positive statement. Plus, I really think you'd feel a real weight has been taken off your shoulders, once the worry has gone. By shaving your head, you're taking control of the situation, rather than baldness taking control of you. It shows people that you're confident within your own skin, and thats something that girls and guys all find appealing in one way or another. I think you should just go for it. If you really really hate it once you've done it, it'll grow back, but you might just find a whole new type of freedom and happiness once you've taken the plunge
Oh my yes! Shave it. You are going to look just great shaved. Shave it smooth and put a smile on. I think you will find that women are going to find you very attractive. Just relax and be yourself.
You're head will look much better shaved completely bald, and without the cap/hat. Be proud of your bald head!
Go for it - - -and you will realize that you should have done it a long time ago
Do yourself a favor get rid of the hat and the hair.
Your much to hard on yourself your a fine looking guy. But your lack of confidence is your problem,or maybe the type of women your trying to date.The shaving itself may not be your answer.The one thing I can say is never give up, not all women are looking for movie stars most are looking for someone they can talk to and have some fun with.
I would go for it. You won't regret it a bit.
[ But when I did shave last year I was thinking how isn't this a way of concealment also?
It's not concealment. Quite the opposite; you are proudly showing your bald dome to the world. Look at it this way: you wouldn't go around wearing a beard that only grew in on one half of your face. So why should go around with a partially hairy head?
Welcome

If you're not happy with your hair and it is making you anxious and self conscious, you SHOULD try something else. I was in exactly your position 3 weeks ago. I had been working up the courage internally to do it and finally went for the gusto. I immediately felt better about myself and the weight was lifted.
I don't feel shaving is a form of concealment. I think it's a flattering style which works with what you are given. When people ask me why I shaved my head, I don't conceal the reason, I tell them because of the receding and thinning. The response I get is always "I didn't think it was that extreme or noticeable". I think they are right. I was combing it to make it look as good as possible.
The thing is, I wasn't happy with it. So I did something about my happiness. And since I've made the change, I have never felt better about myself. I also love the look and love the feel.
Seriously - don't let this part of life get you down. You owe it to yourself to feel good about yourself. I think you will look great bald and you will probably think so too.
It's not concealment. Quite the opposite; you are proudly showing your bald dome to the world. Look at it this way: you wouldn't go around wearing a beard that only grew in on one half of your face. So why should go around with a partially hairy head? 
I love that analogy

I have guys telling me all the time they wish they could grow a beard like mine. And they are always showing me what sections won't grow on their face

..... so they shave their whole face.
You're absolutely right.... If you can't grow hair on your whole head, shaving the whole head becomes the logical option.
Hello! I'm the wife of Good to Be Bald and just wanted to add my input.... My guy had dreadlocks for the longest, then informed me he wanted to go bald and wanted me to do it for him! I wasn't pleased, but told him I'd give it 6 months for me to adapt - I just associated bald with sickness... It didnt' take me long to learn to love the bald man! Shave it and love it! This woman finds her bald man to be very sexy....
Let's be honest, you're almost there anyway. Shave it. You're going to look great with a shaved head. And you know what? The act of shaving your head itself is going to give you a boost of confidence. It will honestly feel like you are conquering baldness by embracing it. I'm 100% with what the others have said here.