Requesting Reimbursement: When you’re consistently footing the bill

by epi on April 23, 2012

Q: My friends and I are all professionals who typically go out to dinner and/or drinks two-to-three times per week, and enjoy various activities on the weekends – both in our home town and away. In a group setting, the same few people are consistently buying rounds of drinks, coffee, or covering small expenses for the remainder of the group. We never see reciprocity from these other friends. While it seems petty to ask for $5 or $10 here and there, the aggregate cost of repeated freeloading is significant. What is the best way to approach our friends’ penny pinching ways?

A: There is no “best” way to suggest that your friends reciprocate. In the future, you might just consider ordering for yourself alone instead of offering to buy a round of drinks, coffee, or whatever. If another one of your friends also orders something, when served and assuming you are expected to pay at that time as opposed to running a tab, you would then only pay for your drink. Another alternative would be to say something along the lines of “John, I think it’s your turn to pick up the tab.” or “Sue, your share is $5.00.” or even “Steve, since I paid for the drinks, do you mind paying the tip?” It’s your choice.

{ 2 comments… read them below or add one }

Elizabeth May 19, 2012 at 12:40 pm

A friend recently cancelled a trip with me at the very last minute. I called her the day before we were leaving and she let me know then that she might cancel the next day due to work. I was a little stunned. I was also very busy working and let her know that I was going to take work with me. (Perhaps she could do the same?) The day of the trip she left a voicemail for me that she indeed was cancelling. She offered to pay her portion of the room. I was so busy with work and also so hurt and confused, that I didn’t call her back. She reached out to me regarding dinner and we are now getting together, a couple months after the trip.

I had signed up for the trip myself with the understanding from the organizer I could have a roommate. If she had told me a couple weeks in advance, I could maybe have found someone else to go with or could have cancelled. And yet I may have gone alone, but perhaps not. I would have certainly considered all options which I couldn’t at the last minute. Given the uncertainty of all of this, does she owe me 1/2 of room fee ($230.00) or some portion less?


Elizabeth May 19, 2012 at 1:20 pm

Elizabeth, it sounds like your friend put you in a real bind. I think what you should have done is: when she called the first time, take a minute to collect yourself and respond in a clear manner. It sounds as though you did not respond clearly (i.e. object to the possibility of her cancelling), and so she assumed it was ok. Your response could have been: “Deb, you know I’ve already paid for the trip, and I only signed up for this trip because I thought it would be fun with two people and because I wouldn’t have wanted to spend the full amount on my own. I’m not sure why you didn’t think about this sooner, but if you don’t go on the trip, you will still owe me your share of the room. It’s really not cool of you to cancel like this at the last minute, because had you done it sooner I could have found someone else to go, and now I can’t do that.”

At this point, she knows that you’re upset. You can still essentially say the above script, letting her know that she made a commitment and didn’t follow through, and that you expect her to make things right. Barring a true emergency, it’s never ok to cancel on someone last minute for a trip like this.


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