DEAR HARRIETTE: My two best friends and I go out to dinner every Friday night. We started this tradition after I got a huge promotion at my job and treated everyone to dinner. This happened several months ago.
Both of my friends have their own jobs and make good money. The problem is that they still expect me to pay the bill every time we go out for our Friday dinners. I don't do it every time, but they always suggest. It makes for an awkward evening when they consistently suggest that I handle the bill. When I asked them why they always think that I should cover them, they said that it's because I have the highest-paying job. They also say that we pay for each other all the time, and it's not a big deal. It is a big deal because I've never asked them to pay for anything I do, and I always handle my own tab. I'm thinking I may want to stop the Friday dinner tradition altogether. What should I do? Why do you think they keep doing this? -- Split the Check
DEAR SPLIT THE CHECK: You set the standard when you started this tradition by treating everyone. You will have to change it, or else it will remain awkward. You can tell them that it feels uncomfortable now when you guys go out because you realize that the expectation is that you should pay. Remind them that you paid that first time because you were celebrating and wanted to treat them all. Now that it’s just your time together, you do not want to be obligated to pay for everyone. You believe it should be shared. Tell them you don’t want this to be awkward for anybody, which is why you want to talk it out now.