You seem a little vain. I can understand the insecurity because everyone judges everyone. Either outwardly or inwardly. I wouldn't have a problem dating a woman in your situation. But I am not much into vanity. That being said too, I am not like most people. Sure, I love a hot chick, but that doesn't make or break it for me. I live in reality and realize we all have flaws. The key to finding happiness and someone who you like is looking past the flaws to what makes them good and appealing. Part of this equation is you letting go of some of your hangups. Kudos to you for being honest with the guy at the bar. But, really are you going to meet anything other than a sex partner at the bar? Not very likely. Channel and utilize your confidence and that will be very attractive as well. Confidence is a hug attractor for both sexes. If I meet a woman who lacks confidence, I see her as an easy target so to speak and easy to bed. But no way could maintain a relationship with someone who needs constant reinforcement/support. That gets old and I have been there.
I am not saying lower your standards, but realize that some ( a lot ) of people are vain and therefore that reduces the amount of people who can see past it. Another option and to make life easier in the sense of filtering through the douchebags is embrace it and quit wearing the wig. Again, this requires confidence. Any guy who approaches you obviously wont care.
Now, me being a guy and a pervert.... Does this affect your other area as well?