There's something I've noticed w/ the guy I'm dating that I've never been quite sure how to react to. I'll label it as either defensiveness or anger (though neither of those is quite right). It's always re: money... or women... or relationships/marriage... or people who "want something." It's as though he's afraid of being used. For (what I assume is the) context, he's been divorced twice. [His first wife has borderline personality disorder & his second wife cheated.]
While I do want something (i. e. a mutually loving, mutually supportive relationship), I have no intention of hurting/using anyone.
Most Helpful Guy
The truth is that men get used a lot. Women who have not romantic interest in you will often accept a date and a free meal/movie knowing all along that it won't go anywhere.
Once loving wives, can make money grabs when the divorce happens.
It can make some men very defensive when they think they might be used.
On the other hand, a man's value is directly tied to his ability to protect/provide.
I would make a big effort to suggest dates that are either very cheap or free. Dinner and his/your place and Netflix can be a better time than a movie and a nice restaurant, but won't make him feel used. If you want him to drop his guard, you need to show him that you are not interested in his money.1