I come from a culture where men pay. To a ridiculous point - in 2008, when I went back home with my then H and two daughters, I was in a restaurant and I ordered our meal and the waitress was confused to death when she returned at the end of the meal because she did not know whom to give the bill to - to him? but he did not order; to me? but I am a woman. So I have never paid for a date. A couple of years ago a picked up a copy of Dating for Dummies at my local B&N and read that women are supposed to pick up the tab every once and a while. How do you know when the right "while" is and how do you do it gracefully? Does income distribution figure in the equation (I would most likely date people who make much more money than I do)? I thought that as a solution I can invite a man over for 1) a meal (I can cook restaurant quality meals) 2) wine and cheese 3) tea with sweets. I can easily pull off any of that, expending money, time, and labor=being nice, and I would enjoy doing that. There are two problems. First, I am messy. I have a messy apartment full of unpacked boxes, with three cats, with carpeting that has not been cleaned in this millenium - I can only invite select easygoing people and not OCD clean freaks over. Second, I am afraid that unike a restaurant date an invitation to my apartment would be regarded as an invitation for sex and what if I am not yet ready for that? So my solution has limitations. With the right easygoing person who is not looking for a Martha Stewart in the bedroom and whom I am ready to be intimate with, it is a good solution. But not otherwise. For the rest of the situations, I need some hard and fast rule. Offer to pay on every Nth date? How insistently?