First Painful Conversation...(I chickened out and had it over email!!)

So this guy I have been dating has been a little cheep on dates. I was out with him and my friend, and he threw down a few bucks shy of what he owed. My friend exploded in characteristic drama, and he felt embarrased and called me to apologize for being cheep. It gave me the opportunity to clarify expectations. I didnt want to call him to tell him what I was thinking, and I didn't want to wait until it was too late!! So I wrote an email:


About money--I appreciate you calling me and saying sorry. I think in dating money gets confusing, because guys used to have to pay all the time, and girls usually don't make it clear one way or the other what the expectation is.

I want things to be equal because I want to be in an equal relationship. But I don't want to go dutch! Its too sterile. It reminds me of the following scenario: instead of two friends buying each other a present, each person just buys themselves a present! Its not very special to buy yourself a present. Its much more fun to give one, and get a cool one from your friend. But it takes trust--because maybe your friend will forget about you!

I think what we should do is take turns taking each other out. The conversation could go like this:

"Hey, I want to take you to dinner"
"thanks! That would be great."

Then we can switch.

Or we could do this conversation
"I want to pay for this"
"no you payed last time, its my turn"
"no"
"yes"
"no"
"Ok you can get it, but I want the next one!"

It seems trust building--you know that you can be generous, and you know that the other person won't take advantage of it, because they are generous too.

At the same time, we both don't make a lot of money, and I am supposed to be saving because I am about to be living off student loans for a couple years while I finish my master's degree. So I am all about cheap/free fun.

But if we do go out, lets do it generously :)

Jaim