I've been dating a guy for a couple of months now. He is a really good guy. He works, is honest, and truly just wants to get his life together for himself and his 2 children. I know he struggles with money-not because he doesn't work, he does-but because he is a good father and is working to save for a better place to bring his children to in hopes of sharing custody 50/50 in the future while paying to live right now. Sooo...I really want to bless him with a little cash. I have checked my motives and I do not want to do it to try to buy his love or make him think any higher of me. I really just want to bless him. He deserves a break...a blessing that will help him to where he is trying to go. Is it ok for me to send him some cash in the mail? Should I do it anonymously? face to face? Or would the whole thing be an insult to his manhood?
Update: The question itself has a typo! It is simply "is it ok for a woman to give a man money?"
It is a difficult accepting help from a woman or a man if one is self-sufficient. You are doing nothing wrong, in fact it is admirable you care enough to want to do somehing that nice. He may have pride issues with accepting the gift, if he doesn't then something is amiss, and it has nothing to do with you being a woman. There are times in life when a little unsolicited help is great but we should always want to make our own way. Do what you feel just watch his reaction. Don't ever be scared to be nice. We need more of that in this world.
The thing would insult his manhood if he is actually a good guy, but at the same time I think you're being disillusioned as to think he is such a great guy. Granted I don't know him but everybody earns their own situation, and he seems in a BAD spot right now. Do you really want to be dragged down into this?
Giving and taking money is always a really hard decision to make.
First off all: what exactly do you mean by "give him money so he can take a break"? Of how much money are we talking here - what intend would you like the money to be used for? Given those answers you may find others ways to help him than rather giving him the money directly - like spending a weekend with his children someplace else on your bill. If he accepts that, he might be open to other things, too.
Though all this surely depends on how far your relationship has developed...
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