No, destroy his confidence and instill new insecurities, THEN break it off. Might as well get something out of it.

Same thing happened to me. Know that you deserve more

Maybe but not always the case. A sweet guy who is insecure builds up no self control over temptations. U take away the crippling insecurity and u end up with a guy who without being prepared for it will get female attention without knowing any self control. I used to be and still at times am very insecure but at times I am comfortable I sometimes get presented with very tempting offers to just say the least. For me the fact that I know I get a great deal of my happiness from my wife and kid keeps me from temptations like that, without that I might havebeen tempted back then. By now I can easier resist temptations anyway. But to say he was always like that? U can never know if he was or just not trained to resist temptation.