TGIFormspring?!? It’s time to answer a reader’s question:

What's your recommendation when it comes to paying for dates? I get the first, the second, but if you are into a guy, is there a point when you should offer to pay (or at least pay for half) so that you don't seem like a gold digger?

Answer: This is a great question! It might be easier to solve the Riddle of the Sphinx than figure out who should pay for a date, though. In a discussion a few weeks ago with friends at Lincoln, several women were adamant that a guy should pay all of the time, unless the female was taking the guy out to celebrate a special occasion. They reasoned that the guy wants to feel useful and show that he's a good provider. One man in the group adamantly disagreed, viewing this as a feminist issue. In his opinion, the cost of dates should be split 50/50 to ensure an equal power dynamic.

I posed variations of your question on Formspring, and the general consensus was that whoever asks the other person out on a date should pay. A few women chimed in that they hope that the man pays for the first date as a sign of his genuine interest, but then the person who does the asking should pay. A male friend commented offline that he feels like there are women who expect the guy to always pay for dates, and that it’s nice to have the woman pay for an evening once in a while.

For most of my dating life, I’ve been the type of woman to offer to pay, but yet I judge a guy a bit if he allows me to pay for half of the bill. (I think some of that has to do with the fact that I don’t drink so if the bill is split, then I end up paying more than my share. But, I don’t want to squabble on a first date over $5 or $10, and I had viewed this as a feminist issue.)

I’ve changed that mode recently, though. I've realized that when I’ve truly cared about a guy, I’ve always invested more in the relationship in every sense of the word. I’m not interested in repeating that pattern again. Initially, I’d like to be courted a bit, and then if I make it to a fourth or fifth date with a new man, I’ll take him out somewhere nice. I’m not offering to pay my way, but rather just saying thank you in person and later by text. (For those who are wondering, these guys asked me out so it does follow the notion of “Whoever asks should pay.”) I feel more comfortable in this mode than I felt offering to go dutch.

Since your question assumed that the guy will pay for the first two dates, I think you can ask him out or arrange a fun evening for the two of you in your first month of dating and then pay for that date. It's worth noting that a woman who expects a man who asks her out to pay for the date isn’t a gold digger. Most guys will be able to sense if a woman is trying to take advantage of him because of his money, as those traits will often exhibit themselves in other arenas beyond who pays for dinner at the end of the night.

If you have the expectation that the guy will be paying for the first few dates (and that’s not necessarily the wrong expectation to have, depending on who does the asking), there will be some level of comfort between you two after several dates. It’s possible to ask at that point how he feels about the “Who should pay on a date” issue. Likewise, you’ll know more about his general financial situation and whether it makes sense for you to contribute more when you’re together. (If he’s in graduate school and you have a steady job, you might be more inclined to contribute more than if you’re making significantly less than he is. If he makes significantly more than you do, then my male friend's idea of taking him out now and then should be especially well-received.)

Based on Facebook comments, people are very passionate about this issue.

So, folks, how do you deal (or how have you dealt when you were dating) with the issue of “Who pays?” What suggestions would you give this reader?