Dear Dategirl,

I’m a 40-year-old, attractive, successful woman and have been divorced for six years. I’ve had several serious relationships since my divorce, and I notice a pattern I have been perpetuating: I keep dating (and was married to) men with no money or ambition, and I end up being their sugar mama.

I own a house and a nice car and have worked really hard for what I have. Although I’m a nurturing soul, which I suppose is what attracts these guys to me in the first place, I have finally had enough of the taking, when all I do is give both emotionally and financially.

The men I date are attractive and charming, and somehow I talk myself into the fact that that is enough and even though they have no money, that is OK. I am not hung up about needing to be with someone who is rich; I just don’t like feeling taken advantage of.

I’ve talked to friends about this, and they think I’m overreacting. My current boyfriend is cute, smart, and funny, but has a crappy job and no plans for the future. He lives in an apartment and owns very little. He treats me really well and is sweet and complimentary, but I can’t help but feel that of course he’s into me, because I pay for most of our meals and entertainment, and when we go out I drive (because his car is too much of a mess for me to drive in, apparently).

My question is, should I try to change my attitude and just be thankful to have a nice guy in my life, and make plans after dinner, so I won’t have to open my wallet every time we meet up? Or should I just go with my discomfort and try to find the elusive, successful, nice guy, who wants a partnership with an equally successful gal?

Sugar Mama

As someone who lives in a rented apartment, owns very little unless you count books, and has a retirement account so tiny I’d best die young, I’m trying hard not to be insulted. And I don’t even own a car, so I’d be taking you on dates via bus. Harrumph!

Anyway, stuffing my indignation back into the closet and putting on my advice cap….

My answer: People treat you how you let them. Quit reaching for the check all the time. In a relationship, both parties should give as much as they’re capable of. If he makes less money, then he takes you to less schmancy restaurants, and you suck it up and eat falafel instead of filet mignon because he’s trying. And if you insist on linen tablecloths and fusion cuisine, well, then, pull out the platinum card because that meal’s on you.

If ambition and success are so important to you (and believe me, nothing wrong with that at all), I wonder how you keep ending up with the exact opposite of that. Do you think maybe you pick these financially deficient men because you enjoy the sense of power being the alpha wallet provides? Or maybe you secretly think that money is the only thing you have to offer. Have you ever given either of those scenarios a good, hard think?

Again, let me stress that I’m not putting you down for this, just wondering how much you’ve thought about it. Personally, I had a hard enough time locating kind, smart, cute, and funny without worrying about what was in the wallet. It’s only sheer happenstance that I wound up with someone who makes more money than me—though he’s not rich by any stretch.

One very realistic and admirable thing about you is that you’re not asking me how you can transform a slacker into a captain of industry. You just need to figure out if a fat bank account is more important than a cute smile, a sharp wit, and a kind word when you need one. Because there’s usually a trade-off.

And let me leave you with this—rich, successful men have been dating hot, broke chicks for aeons. Why do none of these guys ever write me?

Judy McGuire is the author of How Not to Date. Dating dilemmas? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.