I have been twice divorced too and I understand the stigma attached to it.I’m 45 and back on the dating scene again after 10 years of marriage ended.Both sexes have reservations about trust,especially this day and time.
I’m not here to give you advice just to empathize with you.If was cornered and had to give some I guess I’d say to ask him how to gain his trust.It may be different for each man.