WWYD: Tipping on a Discounted Meal, Being Assertive

Today in “WWYD,” one of our favorite topics: tipping. And learning to be assertive.

I’m curious about how to tip when something has been removed from your bill. I went out to breakfast with a friend and my food came out the way wrong. Without saying anything to me about it, the server kindly removed it from the bill. I left the tip for our table, and left him 40 percent, which seemed reasonable as I was leaving it, but when I calculated it more precisely at home, I realized that I only tipped two dollars more than what his tip would have been if my food were on the bill. So now I’m concerned that I low-balled him.

Do you have any guidelines for what I should do in the future? I want to be generous to someone who has been generous to me, but if I’m being honest, I guess I also don’t want to pay back the entire cost of the bad food in the form of the tip. Or would that be the best thing to do? — M.

Perhaps our readers who have worked in the service industry can help me out on this one, but it seems to me that if you really want to be generous to your server, the thing to do is, well, tip generously. Generally, when you get comped items, I think it’s a good idea to tip as if your bill wasn’t comped at all, which is what you did. Continue to dine at that restaurant. Be kind to the servers, and tip generously for the great service. That’s the best thing thing to do.

Just over a year ago, I was awarded a scholarship for students in my area of study from a community foundation in my area. The scholarship fund is supposed to give me $500 per semester for the remaining years of study. I received the award no problem during the Fall semester of ’11 and Winter of ’12. Then I took the Fall semester of ’12 off. Now I’m back in school, and there’s been no indication that I’m getting the $500 this semester.

The last time I spoke to anybody at the foundation, it was early August of last year and I was still planning to be in school that fall (and graduate in December). Since they were waiting on my enrollment certification to send me the money (I have to be in school full-time to be eligible), I figured they just didn’t send it that semester, since they never got my enrollment certification, because I didn’t enroll. I sent them my enrollment certification for this semester, once I went back to school, and assumed that would set things in motion for me receiving the award again.

But the money hasn’t come, and I’m feeling super guilty because I have been really bad at communicating with these people — I never told them I was taking the semester off — and I want the money because I’m a poor college student and I could really use it (and, you know, I was awarded this scholarship and everything). But I really don’t want to write to them and ask because the whole thing is going to be me saying, basically, “Um hey, remember me? You gave me a thousand bucks and then I kind of disappeared and didn’t send a letter to the trustees updating them on how my education was going even though I promised I would do that? Well, I’m back in school now and I would really love it if you would keep giving me money, ha ha!” I’m going to be graduating in May — finally — and I won’t have to deal with this again after this year.

Do I avoid the humiliation and never ask for the money and remain quietly resentful of them and myself? Or do I risk it and write them a nice letter and explain what was going on and see if they got my enrollment certification for this semester? The answer is SO OBVIOUS when I write out the question like that, but I am just really bad at asking for things I want, especially when I feel like it’s my fault somehow that I don’t have the thing I want. Also, how do I write this letter? — N.

So even though the answer to N.’s question is obvious and she basically answers it for herself, I wanted to post her question in full to show how helpful it can be to write out a problem you’re having and examine it on the page. Yes, clearly N. needs to get in touch with the foundation and get this all sorted out. And the easiest way to go about doing that is to pick up the phone and track down a person who can help her get this matter cleared up: “Hi, I’m a scholarship recipient and haven’t received my funding for the current semester. Can you connect me to someone who can help me?” Once you’re connected, explain the conundrum, just as you described above.

It’s hard to be assertive if you’re the shy, non-confrontational sort of person — the sort of person who over-apologizes for things. I know because I also tend to lean in this direction. But I’ve also learned that if you don’t assert yourself and ask for things, you lose out. I saved myself a lot of money by asking for more financial aid when I was in college. I asked for and negotiated a smaller broker’s fee for the apartment I currently live in and saved myself $1,000. And as Rebecca says in her Craigslist piece today, you’d be surprised by how much you can save simply by asking for a discount.

I’d skip the letter and pick up the phone. You’ll get this resolved much more quickly.

Email me your WWYD experiences to me with “WWYD” in the subject line. See previous installments.

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