Going Broke in the Dating World

(NOTE: Jim's blog is now devoted to answering relationship questions submitted by readers. Please send any questions you may have to jim@attorneyatlove.com).

DEAR JIM: I'm 46 years old and have been divorced a little over a year. I'm paying $950 a month in child support, and I'm still paying half the mortgage on the house my ex-wife and kids live in, plus the rent on my own apartment. I'm fortunate to have a decent job, but I have very little discretionary income at this point. I've met a few women through an online dating site, but every date I've gone on has been expensive and has lead to nothing. I hate to look cheap, but I can't afford to drop a hundred dollars or more on a first date with someone I may never see again. Is it OK to go Dutch on a date, or would it be the kiss of death to suggest it? ("Ron" in Connecticut)

DEAR RON: Before I answer your question, let me suggest an alternative. You don't have to spend a hundred dollars on a first date, regardless of who pays. In fact, even aside from the money involved, it's crazy to go to dinner at a nice restaurant with someone you barely know. If the chemistry isn't there, you'll both realize it before you've finished your first drink, and for the next hour or two you'll be making uncomfortable small talk while at the same time running up a substantial bill.

First dates should be in places that are inexpensive and where there is no automatic expectation of a lengthy time commitment. A coffee shop is an ideal venue for first dates; you'd have to buy a lot of lattes and pastries to drop $20 or $25, and you can make a graceful exit after thirty minutes if things aren't going well. On the other hand, if things are going well, you can usually linger as long as you'd like, or just leave together and take a nice stroll.

Another reason not to spend big bucks on first dates is that the woman may feel you're trying to buy her. This is one of those issues that cause a great deal of mutual misunderstanding and mutual resentment. The man feels that the woman is happy to let him lavish his money on her, and the woman feels that the guy is acting like he owns her. It's a common problem in the dating world.

Getting back to your question about going Dutch, I personally don't like the idea, unless the woman insists on it (there's nothing to be gained in arguing with a woman). If you're keeping your costs to a minimum and not obviously hinting at a "quid pro quo", you're more likely to come across as a man of sophistication if you pick up the tab. I may be old-fashioned in this regard, but I think that, when it comes to women, a little treat is never a bad idea. But keep the treats little, especially on first dates. You don't want to miss a child support payment because of too many fancy restaurant meals.

Good luck, Ron, and let me know how your next date goes.