Dating becomes infinitely more enjoyable the moment you stop seeking her approval.
Let go of the need for validation or comfort from these women. Times (modern women) have changed, it is no longer 1950, finding a virgin is tantamount to finding bigfoot riding a unicorn. See them for what they are now, experiences, not "she's the one."
Nine times out of ten, the woman sitting across from you won't be yours, it'll just be your turn. Realize that there is nothing wrong with knowing this. So relax, work towards raising and owning your value, and enjoy the ride without losing yourself in it. Life is too short Gentlemen, onwards, we are Men of Action.