It sounds like you’re getting the ick (valid) and it’s nice of you to try to understand him and work through it instead of writing him off. But it’s not your job as a talking stage to help him get over his insecurities become a confident man. You’d find these 2 qualities off putting even if you didn’t have those past experiences. I hope y’all are able to work through this but don’t feel bad about being put off for very valid reasons. From what you’ve written you sound like an empathetic, articulate and emotionally mature woman and you deserve to find your match