Can You Ever Assume That Someone Else Will Pay? (With Fingers Crossed )

Mike Dang: Logan, I’m on my way to a wedding right now! I think there is a rehearsal dinner tonight. Probably fancy? Not sure? Also, I’m bringing a wallet full of cash. Rehearsal dinners are usually paid for by the parents of the bride or groom, but I don’t want to be the one without cash if that’s not the case here. ASSUME NOTHING, basically.

Logan Sachon: OH, HM. I would never consider that. When parents are involved, I always assume everything is covered. But that’s obviously a pretty classist assumption. I do still offer to pay for my share or the tip or something, fully expecting the answer to be no. Like, FULLY. But not at a wedding. You never pay at a wedding!

MD: Yeah, I’ve never heard of anyone going to a rehearsal dinner and then having to pay for him or herself, but I like being prepared anyway. I’m also trying to think of a situation where I was out with someone else’s parents and they didn’t pay for me, but I can’t. It’s part of the parents handbook, probably. “Consider paying for your child’s playmate when out to dinner.” — Dr. Spock

LS: But yes, I think it’s a good idea to always be prepared to pay for your own meal. Like, duh! I think it can be tricky though if someone invites you somewhere you know you can’t afford. A friend was in town recently and invited me out to dinner—she had the place picked. There was no chance she wasn’t going to pay. Okay there was a small chance. But I was 99 percent sure she was going to pay, though it still felt really kind of dicey.

MD: Whenever I get invited anywhere, I’m always prepared to pay, so if it’s something I honestly don’t think I can afford to do, I’ll just say so. “Oh, I’d love to come, but I really can’t afford to do that right now.” The response is usually, “Oh, don’t be silly, we’re treating you,” but I never want the person to assume I expect him or her to pay.

LS: Yeah, I thought that if I said that I couldn’t afford it, that then she’d feel like she had to offer to pay for me? And I didn’t want her generosity to feel strong-armed. Plus, you know: TALKING ABOUT MONEY. To be clear, though, I COULD have paid, technically. I just would have had some monetary troubles later in the week. Like: Rent.

MD: Haha. WHAT? Logan, if you cannot make rent after spending money, you cannot say you could have paid! You cannot pay for things if it prevents you from later paying your basic needs.

LS: SIGH. What about for business meals? Like, if a BUSINESS PERSON asks you out for a BUSINESS MEETING, they are obviously going to pay right? Is that an assumption? It seems like it would be silly to tell a BUSINESS PERSON, Oh I’d love to meet you for this business lunch, but it’s not in my budget? Like, it seems like it would come across as GREEN and NAIVE.

MD: So let me tell you about my business dinner with a business person from earlier this week. This business person invited me to meet her for dinner at a fancy restaurant. How fancy? Well, Mayor Bloomberg was also eating there that night, and he has billions of dollars (and a team of security personnel who had to stand around and wait for him to finish dinner).

I didn’t order a drink, and I tried to be sensible when ordering, and reached for my wallet after dinner was over, and she was like, “No, no, stop. You are not paying for this dinner. Honestly, I am not paying for this dinner. The company is paying for this dinner.” I forget that real business people have company credit cards they can use sometimes.

LS: Ah and then you must have wished you got the steak, and app, and ten cocktails! I used to work in a job where I had a lot of meals out with people who expensed them, and it was great fun. But it was also generally explicit and expected that it was going to be an expensive meal and that no one would be paying for it themselves. Did you wish that she had said something beforehand? Or that you had asked?

MD: No, I actually feel nervous drinking around people who aren’t my friends. And also, when I get nervous, I lose my appetite, so it all sort of works out!

LS: Okay, but what if you really couldn’t have afforded to eat anything in that restaurant. Would you have not accepted the invitation? Or said, I’d love to but can we go someone cheaper? Is there a way to ask before you order if your dinner companion is paying that isn’t totally uncouth?

MD: This is a good question. And I first want to thank all those people who understand that this is question people have and sidestep it by tacking on three beautiful words on to their invite: “Dinner’s on me!” That’s what I like to say when I’m planning on treating someone, “Dinner’s on me, so feel free to order whatever you want!” But let’s go back to the business dinner I had for an example.

When I got that invite, I immediately looked up the restaurant and scanned menu prices before accepting. I decided it was somewhere I could go and come out alive. I would probably have suggested another place if it was astronomically high. I do think asking at the dinner table is a little uncouth. I mean, would you go on a first date and ask your person if you have to pay for dinner?

LS: No, of course not. But in “business” there are rules. And expense accounts! Like, there is no way that person wasn’t going to expense your dinner!

MD: I will admit that going into it, I did feel that it was going to be paid for, and that was, in fact, the case. But, I guess it’s the same with this rehearsal dinner, I just feel like I want to be prepared for any scenario.

LS: RIDDLE ME THIS!? Could this be an EMERGENCY CREDIT CARD SCENARIO? A dinner where you are almost completely positive someone else will pay, but the card is there … just in case?

MD: Hmm. Sure? Logan, I have all your credit cards though.

LS: I’m asking on behalf of other people.

MD: Are you trying to trick me to giving one back to you!?

LS: Ha, no tricks here. But actually I feel like I’m at the point where I want to get them back from you and just cut them up myself. Self-reliance, etc.

MD: Yeah, I think that’s great. I just have to go to Mordor to retrieve them, because that’s where I hid them. I know we’ve been talking a lot about other people buying dinner, but one of the first times I really felt like an adult was when I flew home to visit my parents, and we all decided to go out to dinner, and when the bill came, I grabbed it and paid for it. I think there comes a point in your life where the roles reverse a little bit.

LS: Yeah. I can’t wait until I’m at that place.

MD: Soon, Logan, soon. And when that happens how do you think your parents will react?

LS: I don’t know about “soon,” but …. yeah. Um, I don’t even know. It might come to blows.

MD: Good blows!

LS: Fighting over the check is an honored-Sachon family tradition. My dad and his dad did it. My older brother and my dad do it. My little brother and I do it … though we’re both broke so it’s more like, “You pay, no, you pay!”

MD: Haha.

LS: But one day, I’ll beat up everyone and pay for dinner. It’ll be great.