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

Let’s get one thing clear: if you invite your friends as guests to a dinner party, it’s crazy to follow up with a Venmo request . However, beyond this should be obvious etiquette, money habits between friends are often tricky territory to navigate. (In fact, I’m arguing that there are plenty of ways to stop being an asshole on Venmo .) The correct way to split the bill may seem obvious to you, but it will be different for your friend across the table.

Money can be embarrassing to talk about, but it’s best to work out any issues with friends right now. After all, these problems will not go away, and unresolved violations over time will only lead to resentment and tension. Here are some of the most common money expectations 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 giving advice unless he asks you directly. Think you might be making unsubstantiated comments that are not strictly “advice” but are unwelcome insinuations nonetheless. Examples include:

  • Why don’t you ask your parents for money?
  • Why don’t you shop at that other store?
  • Why don’t you invest in cryptocurrency?
  • Why don’t you use [x bank account type]?
  • Why don’t you pay off student loans before interest resumes?

In general, don’t ask a friend why they don’t do this or that financial business, especially if you don’t know all the details of their finances. Unless your friend is in serious financial trouble and is asking for your opinion directly, it’s probably best to keep your mouth shut.

Open up a wider conversation about money

To talk about money while avoiding the examples above, your tone is important. After all, I’m all for talking about how much money you earn . Transparency is important so that we can all learn from each other’s money mistakes and make sure we’re getting the best possible financial footing.

If you blurt out your salary without being prompted, it may seem like bragging rights or at least make others uncomfortable. Instead, test the waters to try and start a broader conversation about money. For example, you could say, “I have a personal question because I’m not sure my pay is fair. Are you dealing with the same issue? If you are ready, could you share how much you earn?” The key here is to respect people’s boundaries if they clearly don’t want the conversation. We hope, however, that you will open the door to sharing realistic expectations and practical advice in this economy.

Don’t think it’s the “richer” friend who pays

Whenever you make a guess about who pays without any clear communication, there are no winners. If you earn less than your friend, it is rude and burdensome to assume that he automatically pays the bill. If you earn more than your friend, it may seem offensive and overbearing to suggest that you are paying for him.

And, of course, it’s tasteless when a friend who makes more money insists that his friends make less. At the same time, if you’re a friend who earns less than your rich friend, you can’t expect them to notice you endlessly. It all depends on your relationship with this person, so it’s best to state your position here as clearly as possible.

Warn your friends

If you owe money to someone or need them to pay you back, do your best to verbally confirm when, how, and how much money to send. As a general rule, sooner rather than later is better for everyone involved. If you can pay off at the moment, it will be preferable to the uncertainty and forgetfulness that grows over time.

We can’t always pay off our debts right away. If you have to wait until the next paycheck to pay someone, just let them know – if they are your friends, they will understand.

Key Point: Respect Boundaries

As in small countries, each group of friends has slightly different money customs. You can avoid the resentment and discomfort that comes with having different expectations about money if you start a broader conversation about exactly what those different expectations are. And although I am for greater transparency between friends, do not insist. Chances are your friendship is more important than the twenty bucks they may or may not owe you.


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