I don't subscribe to the "don't worry about it" mantra.
His inexperience will make itself apparent to any HB. He can't deny this and telling him that it doesn't matter is very arrogant. Any decent, good looking and experienced girl will be able to tell.
With that said:
Why haven't you had any experience to date? Are you Mormon? No offense, it would just explain a lot.
Regardless, your first step is to realize that you are abnormal in your lack of experience. Most guys and girls by your age have had plenty of experience. Don't play these stupid mind tricks. Don't try to temporarily psych yourself into believing something you really don't. It won't work. You'll fall back into your routine neuro-patterns after your first rejection. And trust me, you will be rejected. As a side-note, denying that you fear rejection but alluding to your fear of a woman feeling awkward about your inexperience is practically, and for all intents and purposes, the exact same thing. Don't try to fool anyone here, especially yourself.
Furthermore, confidence is built on a foundation of success, not failure. As of right now, you have neither. The catch-22 is, you can't gain confidence without risking rejection, but rejection will only cause you to feel even more uneasy about your short-commings and thus thrust you further into a cycle of self-loathing bitterness.
So what do you do? You take those risks. And in that risk-taking process you will find yourself. You will have won some, and lost some. But you must get back up and fight again. This is war gentlemen. Your feelings, your self-worth, your pride, and your life is only yours. No one outside of your close friends and family gives a s#!t about you. Knowing this, and feeling the strength in overcoming challenging situations induces powerful feelings of accomplishment. This is confidence. Embrace it!
Seduction is not a matter of trying to figure women out, but of figuring yourself out. Right now, you are in a squalor of denial, and even though you probably won't admit it; self-hate. You must remove yourself from this pit of depression and elevate your standing; both socially and psychologically.
Make the most out of your life. Don't deny your basic primal urges. Don't fool yourself, seize the day. Find your passion and dedicate your life to it.
Women can be an amazing compliment to your life, but can also be the bane of all that is precious and worthy of your effort IF you don't realize that ultimately it is YOUR happiness that matters.
Hope that helps.
