What is it about you dating alone that triggers? Is he worried you will get hurt? He will not be known? What about him coming for the first meet up so the other person knows he exists? Could keep talking there.
If he really does not want to date, what does him dating and being there solve for him? What is is his need? Could it be solved another way? Could he circle?
Counseling wise I do not know if this could help with its links...
If part of the problem lays in communication style, maybe talking with sheets helps make it less aggressive/defensive. Then you can just mark where you leave off. You do not have to do it all in one go. And it is only a sheet if paper. You could ask if he is willing to read it together and talk.