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Never Ask Your Friend These Money Questions (and What to Say Instead)

No, you cannot send Venmo requests to your dinner guests.
Never Ask Your Friend These Money Questions (and What to Say Instead)
Credit: Monkey Business Images - Shutterstock

Let’s get one thing straight: If you invite your friends over as guests at your dinner party, it’s bonkers to follow up with a Venmo request after the fact. Yet beyond this should-be-obvious etiquette, money habits between friends are often tricky territory to navigate. (In fact, I argue there are many ways you need to stop being a dick on Venmo.) The right way to send a split a bill might seem obvious to you, but is different for your friend across the table.

Money can be awkward to talk about, but it’s best to get on top of any issues with your friends now. After all, these issues won’t go away, and unaddressed violations will, over time, only lead to resentment and tension. Here are some of the most common money expectations that you should and shouldn’t have with your friends.

Don’t give unsolicited advice

Even if you think your friend is bad with money, you should avoid doling out advice without them asking you directly. Consider whether you might be making unwarranted comments that aren’t strictly “advice,” but are unwelcome insinuations nonetheless. Examples include:

  • Why don’t you ask your parents for that money?

  • Why don’t you shop at that other store?

  • Why don’t you invest in crypto?

  • Why aren’t you using [x type of bank account]?

  • Why don’t you pay off your student loans before interest restarts?

In general, avoid asking your friend why they don’t do a certain financial thing, especially if you don’t know all the details of their finances. Unless your friend is in serious financial trouble or asks for your opinion directly, it’s likely best to keep your mouth shut.

Do open a larger conversation about money

In order to talk about money while avoiding the examples above, your tone is important. After all, I’m in support of talking about how much money you make. Transparency is important so that we can all learn from each other’s money mistakes and make sure we gain the best financial footing possible.

If you’re blurting out your salary unprompted, you might come across as bragging, or at the very least make others uncomfortable. Instead, test the waters to try to start a larger conversation around money. For instance, you might say, “I have a personal question, since I’m unsure if my pay is fair. Are you dealing with the same issue? If you’re willing, would you share how much you make?” The key here is to respect people’s boundaries if they’re clearly unwilling to have this conversation. Hopefully, though, you’ll be opening the door to sharing realistic expectations and actionable tips in this economy.

Don’t assume the “richer” friend pays

Whenever you make an assumption about who pays without any clear communication, there are no winners. If you earn less than your friend, it’s rude and burdensome to assume that they automatically pick up the bill. If you earn more than your friend, it’s might be insulting and overbearing to assume you pay for them.

And sure, it’s tacky when the friend who earns more money insists on nickle-and-diming friends who earn less. At the same time, if you’re the friend who earns less than your rich friend, you can’t assume that they’ll spot you indefinitely. All of this depends on your relationship with the person, so it’s best to communicate your stance here as clearly as you can.

Do give your friends a heads-up

Whether you owe someone money or need them to pay you back, do your best to verbally confirm when, how, and the amount of money that needs to be sent. As a guiding rule, sooner is better than later for everyone involved. If you can settle up in the moment, that’s going to be preferable to the uncertainty and forgetfulness that grows as time passes.

We can’t always pay our debts right away. If you need to wait till your next paycheck to pay someone, just let them know—if they’re your friend, they’ll understand.

The bottom line: Respect boundaries

Like small countries, every friend group has slightly different money customs. You can avoid the resentment and discomfort that comes with different expectations toward money, so long as you start a larger conversation about what exactly those different expectations are. And while I’m all for increased transparency between friends, don’t push it. Odds are your friendship is more important than the twenty bucks they may or may not owe you.