The holes analogy is good! You made me think: Maybe...as you said, this guy so badly needed to feel 'good enough' --'accomplished' or 'successful'. A twisted version of success for him was to make a woman engage with him even tho the woman knows he's married/in a committed relationship. As though...he was able to convince her to have an affair with him and that's probably (I think?) hard to do, so he feels of high value if he can do that? Or he feels 'successful' because he can make multiple women fall for him at the same time. One is never enough! ;)

The problem with giving someone a chance: After giving this guy a chance, then it turns out he kind of wasn't worth the benefit of doubt I gave him, is that...we stop being willing to give future people a chance. If a guy came along now and said, "look, I once cheated on my wife, but that was due to XYZ and I wouldn't do that again," I'm now stuck thinking "Well that last guy said he would never, ever do it again but..." so...we lose our willingness to give future people that same chance.

But we keep learning, and sharing thoughts about our experiences is also how we learn...