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.