I haven't read all the replys (sorry)

My thoughts .. Money does not make a person attractive.

You mentioned going out and typically not seeing that person again.. that could be a number of things not all your fault or her's.
Get involved with charity work.. You can build great relationships with people whether it be a great friend or more.
You mentioned your smile... maybe put some money into that aspect of your appearance and its also a good health point.

And it is true when you stop looking for that special someone you will indeed bump,ram,trip over them,

Good Luck , I hope you find what you are looking for