Ask Lynn-The Paying-For-Dates Dilemma

He’s interested in an older woman who out-earns him…shouldn’t she pony up the cash when they go out?

By Lynn Harris

ear Lynn,
I am considering a relationship with an older woman, but... The “but” is that she expects me to pay for almost everything since I am the man. However, I think she should pay for dates since she makes twice my income. We have similar expenses and live in the
Don’t break up over money before you’ve really even started dating.
same area, although my expenses are actually greater since I have two kids in college while hers are finished with graduate school. I make just over $100,000 annually and am actually better educated than she is, but her income is at least double mine since she is a surgeon. I am 49, and she is 58.

In essence, I am curious about who is paying for dates these days in the younger man-older woman scenario. I can accept whoever has more money paying if there is a substantial difference in income, regardless of the age of either member in the relationship. Should I just stop paying for dates and see if she dumps me? Please help.
-A man named Kim

Dear Kim,
Hold on a minute: Don’t break up over money before you’ve really even started dating! Look, there’s no “Official Who Pays Scenario” for today’s younger man/older woman matrix — and some people would argue that, with your age approaching 50, the May-December stereotype doesn’t quite fit. Also, there is no simple word-problem-style answer to the question you’ve formulated. (“If my salary is X and hers is 2X, and our age difference is nine years, for what fraction of this surf-and-turf am I responsible?”)

All of that said, what I think makes sense in any mixed-salary relationship is this: To come up with a plan that may not involve complex higher math, but that feels equitable — not necessarily equal, but equitable — to both partners. This means that you don’t whip out your calculators and legal pads and figure out an algorithm based on salaries, years in your field, number of dependents and overall net worth, but you do have a conversation — a preliminary, casual one — about your respective financial comfort zones. And out of that conversation, try to make gentle “rules” that fall somewhere in the middle ground. For example: Whoever does the
Sounds like a bit of unnecessary fuss to me.
inviting and picks the restaurant pays. This means you can spirit her away to a great night at your favorite awesome hole-in-the-wall barbeque and Texas swing joint, while she can dress you up for the Four Fancy Seasons if she’s in the mood. (And you won’t get stuck resenting her doing the latter and then expecting you to drop the plastic.)

But — while you should definitely talk and think about this — I’d caution you not to over-communicate or over-think about it at this early date. I know I teased you earlier about the “word problem” you posed, but seriously, what does the nine year age difference or your being better educated really have to do with anything? Sounds like a bit of unnecessary fuss to me. I agree that you shouldn’t “have” to pay for everything because you’re the man, but I also don’t want this money business to become a bigger issue between you than it needs to be yet. And the fact that you are ready to call the whole thing off worries me that the dollar issue is looming way too large.

Find ways to enjoy and continue getting to know each other — maybe even some free ones! — and then you’ll see if this is someone with whom you’re ready to take on the heavier issues. In other words, have fun now; do the math later.

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website — you can visit BG's blog to discuss this letter! A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your own dating questions for Ask Lynn via Your question may be answered in a future column.
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