Money Manners: When Your Best Friend Earns More…And Always Picks Up The Check

When you earn less than a close friend, it can be awkward to decline invites to pricey meals and vacations. But should you feel bad if the friend routinely insists on paying your way? And how do you politely decline in the event you simply don’t want to go?

shocked colleagueA reader asks, “I have a friend who makes a lot more money than me. She’s single, so she often treats me to dinner out, and even vacations. I can’t afford to go to the places she wants to go, and I love her, but I also sort of feel like a charity case or worse, a paid friend. Should I keep agreeing to go on these trips and out to these dinners?”

Chances are, most of the people reading this article are thinking, “Wait…what’s the problem? You don’t like free vacations?” I didn’t see the problem at first either. But after some thought, I get it.

When someone’s paying for your airfare and lodging, the unspoken rule is that you should do whatever Miss Deep Pockets wants to do on that vacation. Beggars can’t be choosers, after all.

Same goes for dinner. You can’t exactly pick a restaurant if you’re not paying for the meal. And because you clearly have good manners, you feel guilty ordering the special instead of the cheapest item on the menu.

I often mention the statistic that almost half of all college graduates are underemployed. The upside is that the other half are working and a few of them are even making a decent living. Sometimes, friends find themselves stuck in vastly different income brackets. And that usually spells one thing – AWKWARD.

It seems like it’s only awkward for you, however. I’m assuming that if your friend keeps offering to pay your way, she truly enjoys your company and doesn’t hold it against you that you can’t float the bill.

Jorie Scholnik, an etiquette expert who specializes in the millennial market, says, “Friends usually split checks and vacations today. You should make your expectations clear from the beginning so your friends don’t get put in a situation where the activity isn’t in their budget. If a meal or an activity is lavish and there is no negotiation, the person suggesting it should be the one to pay.”

But if the arrangement makes you feel bad, plan ahead so it stops happening. Jorie says, “If you don’t always want to be treated, suggest an activity that is in your price range and offer to foot the bill.”

In other words, suggest the place for your next night out or vacation, and make sure you can afford it.

I bet what she really wants is to spend time with you, wherever you choose to go. But before you turn down any trips to Paris, write me back. I might try to talk you out of it.

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About Patty Lamberti

Patty Lamberti is a freelance writer and Professional-in-Residence at Loyola University Chicago, where she teaches journalism and oversees the graduate program in digital media storytelling. If she doesn't know something about money, you can trust she'll track down the right people to find out. You can learn more about her at And if you have any story ideas, or questions about money etiquette that you'd like her or an expert to answer, email her at