I think this is more about confidence and how you feel about yourself than it is about how you look. Stick with dating girls in your age range and focus more on building up your self-image and some more confidence when it comes to dating. Start to approach girls just for practice. Ask a friend to be a “wingman” and approach two girls together. The truth is that when we feel self-conscious about something, it can keep us from putting ourselves out there. Other people may not even notice the THING we are self-conscious about, but they do notice that we seem self-conscious and uncomfortable, so they stay away.