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If there’s one question that hasn’t been resolved amongst my friends in the many years that we’ve discussed the dynamics of dating, it’s this one: when should you offer to start contributing financially during the courting phase?

A couple of my friends believe that a woman should not chip in until she’s been dating someone for at least two months or are officially a couple. I, on the other hand, believe that a woman should offer to pay for part of the date (not fake offer, but really offer) by the third date. That’s what I believe. But what have I done in the past? I’ve offered even on the first date. If he gets dinner, I offer to buy a round of drinks. (More on that later).

The topic recently came up when my cousin mentioned that the guy she’s been seeing for a few months told her that it would be nice if she offered to pay for things from time to time, since she never offered. She didn’t take offense but didn’t realize it was an issue. Since she’s new to the post-college dating world, she said she didn’t know certain rules.

Considering that all my friends have different perspectives on this topic, I definitely would say there are no rules, although non-oblivious folks have clear opinions on the matter. Those two friends I mentioned previously, who believed in not paying during the initial dating phase, believe that they’re setting a certain standard of how they’d like to be treated. They see themselves as prizes to be won; women to be supremely courted. If they make it too easy for these men, then he would undermine their value. I get where they’re coming from. But I can’t feel it.

What if I knew by the second date that this was probably not going anywhere, but I agree to go out on a couple of more dates just to be sure? At that point, can I really justify not chipping in? My sense of empathy wouldn’t allow it. If he’s not going to win in the end (either via sex or a relationship) then I’d prefer he not invest in me so much.

On a more general level, what about just establishing a level of reciprocity. I’m not saying women should pay for every other date but just chip in here and there. If you go to dinner on the third date, you can offer to get the movie tickets. On a humane level, it just shows consideration. Judging from the experiences of all my friends, there’s no right or wrong way about it. Of course most men would tell you that they would appreciate the reciprocity, but from my observations, when a guy really is into a girl, he doesn’t seem to care at all that he’s picking up the tab so much.

What is your philosophy on this dating conundrum? When do you offer to chip in and what’s been your experience with these type of situations?

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