DEAR HARRIETTE: I have a close group of six friends. “Jane” has always been tight on money, and we've often covered her expenses without much fuss, since the other five chip in. Whether it's going to movies, restaurants or clubs, it's been fine. However, things changed when she started bringing her boyfriend along; now he freeloads off of us, too. We split bills equally, but he always manages to get a free ride.
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After a few outings, I gently suggested to Jane that if her boyfriend continues joining us, they should start contributing, too, as covering for two people is a strain. Her response was unexpected; she asked if we'd keep paying for her if he pitches in. With the way she responded, it dawned on me that their action has always been intentional, and my group felt quite frustrated about it. How should I approach this situation? -- Freeloader Friends
DEAR FREELOADER FRIENDS: It’s time for a heart-to-heart conversation with Jane. While it was nice that you and the rest of your friends covered for her, the fact that you never talked about it has backfired on you. She has assumed that this should be her reality with you and that her boyfriend should inherit this privilege. One or more of you needs to talk to her to explain that she should be able to take care of herself. There is no reason for you to have to pay her way -- or her boyfriend’s. Yes, it may be awkward to address this, but you must. Tell her that her free ride is over. If she decides to stop hanging out with you, sadly you will learn that she was using you the whole time. No matter what, it is time for those days to end.