Brad, you make a better judge of your own decisions or instincts than any one of us from AD could ever be.
Personally I would be turned off if a man tells me that he thinks I wont like him because he is too ugly or whatnot, I dont find these men with low self esteem attractive because I am not interested in falling for their bait. She wanted you to fall for her bait and reassure her that she is a beautiful woman etc - - you sensed that and walked away so dont ever doubt your instincts - clearly you are a sensitive young man if you felt bad for her but it is not your job to make every young single woman or even married woman feel beautiful and desired. That is a tough job to tackle onto.
If you cant do bars or what you mentioned above, then continue with this venue - dont give up - you dont always catch a 20 lb. salmon on first try do you? Keep fishing on, man and you will be glad that you did not settle!