I’ve been seeing one particular woman two or three times a month for an adult relationship (intimate) for about six months.

A papa who makes the poster feel comfortable, I guess. You two meet pretty often. A monthly allowance equal to three pay-per-meeting dates, but in reality you only meet twice? Something might come up, though... I’m a little jealous. If I met someone that often, I’d probably get bored lol. The adult relationship must be really good. Personally, I’d rather meet three people once a month than one person three times a month, so I might not be able to fully understand how you feel.

From a woman’s perspective, it’s easy to see that a monthly arrangement has major advantages, since it provides a more stable allowance. Also, when she says, “Apparently, there are two other women who have monthly arrangements and see him for an adult relationship on a regular basis,” it conveys that she wants you to make your arrangement the same as theirs because the others are on monthly arrangements. From that perspective, you can see that a monthly arrangement offers significant benefits to women. So it’s understandable that she would want one. Now, what about it from the man’s perspective? You could agree to a monthly arrangement, pay the allowance, and then have her suddenly stop responding, leaving you out the amount you paid. Or perhaps you were meeting two or three times a month, but because your schedules didn’t line up, you only met once—yet you’d still pay the same allowance. Those are the disadvantages. I’m sure this goes without saying, but it’s up to the individual to weigh the other person’s benefits against their own disadvantages and decide what to do. If you follow someone else’s advice and things go wrong, no one else will take responsibility for it. With that in mind, here’s my opinion: If, based on your relationship so far, you already know that she’s someone you can trust, then the disadvantages are probably close to zero. And even if things do go wrong, your loss would only be one month’s allowance. At that point, it comes down to how much you like her. So if you like her, I think it would be a good idea to offer her a monthly arrangement, since she’d be happy about it too. Of course, this assumes that you’ve already determined through your relationship so far that she’s trustworthy.

Is a monthly arrangement more beneficial? I prefer pay-per-meeting because it’s hard for me to plan too far ahead. I’m the type who doesn’t like feeling tied down… (•ᴗ•; ) If you’ve never tried a monthly arrangement, it might be worth giving it a shot once to see what it’s like. You could ask her how often she’d like to meet each month and discuss the budget as well (*´︶`*)ﾉ

Even at my age, after having the best sex of my life and heading home feeling completely satisfied and fulfilled, I’m like a paper airplane gliding home. If it were me, and a woman I was seeing—whom I liked that much—asked for a monthly arrangement, I’d either end things or drastically reduce how often we met, perhaps only seeing her occasionally. If there were several things that made her feel especially drawn to you, I don’t think she would keep bringing up something so blunt every time—at least not before you brought it up yourself. For what it’s worth, there was a month when I didn’t think I’d be able to see the woman I was dating very often, so I asked whether I should pay her monthly. She got angry and said, “I’m not that money-minded.” If the woman is the one who brings it up first, I’d assume she’s more of a professional—someone looking for a transactional adult relationship rather than actual dating. Also, in a genuine relationship, both people naturally want to fulfill what the other person wants. So you could choose to anticipate what she wants and offer a monthly or advance payment yourself—or simply date someone you like enough to do that for.

I think you should first ask why she’s suggesting a monthly arrangement instead of pay-per-meeting. If you’re not particularly concerned about her intentions and can’t see any disadvantage for yourself, I don’t see why you shouldn’t agree to it. Whether switching to a monthly arrangement changes the nature of your relationship will depend on her, and no one can predict exactly how things will turn out. Ultimately, it’s a matter of taking a chance, so communicate with her and make your choice.