Experts weigh in on sticky scenarios in which friendship and finances seem to be on a fast track for collision

A group of women in the neighborhood meet for coffee twice a month. Inevitably, one friend asks me to pay for her, promising she’ll pay me back.

She never does.

Yaffa Palti, rebbetzin in Florida:

I’m a big believer in open communication, so ideally this is something that can be spoken about frankly. Maybe something deeper will be uncovered through openly communicating, and the whole scenario can look different. If that can’t work, here’s my go-to: Blame the husband! I feel like there’s a clause somewhere in the kesubah: whenever you need to set a boundary, just blame the husband. “I’m so sorry, I wish I could lay out the money for you, but my husband said we can’t budget in anything extra this month.” End of scene.

Michal Trenk, Director of Students, Tomer Devorah Seminary:

The way I see it, in any interpersonal situation, you essentially have one of two choices: change or acceptance. The reason for your discomfort here is that you haven’t yet committed to either one of those. You’re finding yourself in the same situation repeatedly, yet you aren’t attempting to change it, nor choosing to accept it. That can be a very valid source of frustration.

Let’s explore your options for a change. Ask yourself: is there a way you can communicate with your friend about this in a way that would be efficient and comfortable? (Tip: A little humor goes a long way!) Can you bring to her attention, maybe before the outing, that this time, she should come prepared to pay?

If communication seems to be futile or too uncomfortable for you (which is understandable), you may decide to choose acceptance. Perhaps it’s ultimately worth it for you to let go of the extra five dollars she may never pay you back for the sake of a more enjoyable, tension-free outing with a friend whom you enjoy spending time with. It’s very possible that once you make the choice to accept this pattern in your friend, the five dollars will start seeming negligible in the big picture.

While each of these two options, change or acceptance, may come with its challenges (“I don’t like confrontation,” “I can’t afford to pay for her every time!” “She’ll never get it,” “It’s not about the money, it’s about the boundaries!” “She’ll just think I’m petty if I bring it up”...all valid points!), at the end of the day, weigh which path you prefer to take, and commit to it. You’ll be freeing yourself and your friend from this pattern and setting yourself up for a much more relaxed, stress-free outing.

Work on changing it, or work on accepting it, but choose to make a choice.