About a year ago, I too dated a 37 yr old guy who only had one gf. I don't even think she was really his gf because now he tells everyone that I'm his ex, even though we only went out on 5 dates before I told him things were not working out. I too didn't have the patience to teach him how to be on dates, let alone in a relationship.
There were so many things wrong right from the start. He is awkward, has little social skills and is very clueless.
But his real problem was his personality: he lacks charm. He has so many issues and also lacks self confidence. Plus he is sooo cheap and very set in his ways! When I found that he only had one relationship before that lasted only a few weeks, everything made sense!
Everyone was on my case about not giving him a chance, but I really did. Now I have to add to my ever growing lists of must-haves in my future husband 'prior relationship experience'