Me (36/F) I own a condo and have had a full time office job at the same company for 14 years. I have my shit together and take good care of myself. Him (29/M) no job (got fired 1 month into our relationship), stays on a ranch with crazy people to do work for a free place to live. He has side jobs that he's always out trying to make money with so I don't get to see him much but I am trying not to let hypergamy make my decision on if I should be with someone. He's a felon 3 years clean and sober and almost off probation but has definetly burnt all his bridges except for the ranchers. This is my 1st time dating someone with no $, I mean no $. He never asks for any and he never lets me pay for anything. He's the 1st man I've been with that leads me and is dominant in the bedroom. It's like I finally know what I want from a man because of how Alpha he is naturally. The only problem is his insecurities from past relationships. He projects them onto me. If I am out with my friends (maybe every other weekend and not to the clubs, it's art shows, festivals etc) then to him I am on a date or sleeping with someone. I have never cheated on anyone, it's not my thing. I pride myself on honesty, integrity and loyalty. 14 years in Kung Fu has made me very disciplined with honor in my character. It really hurts my feelings when he says these things. Do I confront him on his insecurities? When he says this shit I do tell him how I feel but I mean should I really sit him down and talk about this flaw in his character? I really like him and don't want to make him feel small. I know he's had horrific relationships in the past and to tell him he has to just trust me after 2 months is unrealistic but trust is almost a deal breaker for me.