[Gracie2006]

This sounds like a "Dear Abby" post. How about, "Dear YT?" Maybe we need a forum for such things? Anyway, I have been dating this man that I met online. He is really sweet. We have a lot in common and seem to be a good match for one another. He got laid off last February. He is putting forth full effort to find work. He has indicated to me that he has financial resources to see him through another 6 months or so.

Here's the issue. Whenever we go out, he insists on paying my way. We don't always do things that cost money, but when we do, he insists on taking care of the bill. I have offered to help out, go Dutch, buy lunch etc. and he won't have anything to do with that. Tomorrow, he is taking me on a cruise and I'm sure we will go out to eat, and then there is parking, etc. Last weekend we went to the local Tulip festival. He paid my way for all of the admissions fees, the tractor trolley, lunch, he even bought me tulips and candy. He drove so gas was on him. It was such a romantic and fun day. It's just that in my mind, this money issue keeps getting in the way.

I understand he thinks if he asks me out, he should pay. I'm sure it's a macho, guy thing. He never expects anything in return. I want him to know I am willing to help out with paying for things when we go out. I also don't want to be a nag about it. I don't want the finances to get in the way of the really good thing that we have going. I think of the $50 here, $100 there in terms of groceries and gas, and of course rent. I've told him I feel guilty with him paying when I'm the one working.

So what do I do:

1. Shut up and let him pay? Just have him over for dinner every so often.
2. Continue to make occasional offers to help out with the tab?
3. Be more insistent about paying my way?

Thanks for your help!