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Dear Heidi: Can I ask for payment via Venmo without discussing it first?

Money conversations can be awkward, but a friendly discussion about how a bill should be divided is smart and appropriate.

We love our friendships. They get us through hard times, help us to celebrate the good times, and support us through both. But one of the most awkward moments in a friendship revolves around money. In a dining out situation, for instance, who pays?

A good friendship involves equity — you both give and take equally. One person isn't doing all the heavy lifting, while the other person takes. We count on our friends, and they count on us. It makes sense to keep everything on an equal footing, so why is it so awkward when it comes to money?

Have you ever noticed a table of friends trying to split the bill at a restaurant? It's hard to watch when it's strangers, let alone your friends. Someone invariably gets out their phone to use the calculator and reduces shares to the penny. Who can stand that?!

Proper etiquette reminds us that a discussion of money is vulgar — but this refers to questions such as, "How much money do you make," or "How much money is in your retirement account?" However, a friendly discussion about how the bill should be divided is smart and appropriate.

The best way to avoid moments of pure payment drudgery is to pre-plan. Decide how you will handle the bill in advance. Sometimes, it's easier for one person to pay for everything, and everyone pays them back. Establish this up-front. These days, it's easy to use Apple Pay, Pay Pal, or Venmo. It's not awkward; everyone expects to see a payment request.

Don't pay and assume that your friends will split the tab with you if you haven't pre-arranged and everyone is in agreement. It is impolite to think your friends will pay if they didn't have a heads-up before your purchase. Please do not send a payment request out of the blue; it will not be received well and could hurt your friendship.

You will avoid all sorts of missteps, misconceptions, and misunderstandings if you set some clear expectations before you hit pay. If you're in doubt about the plan, speak-up. Make things crystal clear, and get on with your treasured friendship.


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