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Who should pick up the tab?

After 10 years of being single, I have started dating a gentlemen who is financially secure and definitely making more money than me. I need advice on how to handle paying the tab when we go out. I feel uncomfortable letting him pay for everything. However, if I insist on paying my half, or even paying for the whole bill, I will have to limit the activities that we do together. How do I politely decline functions that I feel I cannot afford, without appearing uninterested in being with him? Should I discuss this with him? If so, how do I do that without making it appear as if I want him to pay for it? --labottor

Here's some advice that's free. Yes, level with the gentleman about your money concerns, but first make sure you understand their origins. Does your discomfort stem from worry that if he pays on the one level you'll be required to "pay" on another? Or are you uncomfortable with being cast in the traditional woman's role? Or do you simply like to feel that everything is equitable?

Once you examine where you're at on this issue, initiate an honest, non-threatening cash-oriented talk. Have some possible solutions in mind: You let him treat you to expensive functions while he lets you treat him to home-cooked dinners, movie dates, etc. Plus, you can buy him little treats on occasion: a CD you know he'd like, his favorite author's new book (out in paperback), etc.

While neither of you want to feel that the monetary balance must be tit for tat, you should be able to compromise on a fluid, comfortable way to handle the "who pays, when and for what?" hurdle -- one that all couples have to get over at some time or another.

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