Splitting the bill has always been a landscape fraught with social landmines, and new cost-sharing apps only help so much. Here are some suggestions for navigating common cost-sharing situations with grace.

Let’s face it: splitting the bill has always been a landscape fraught with social landmines. For example, just yesterday I read one woman’s story about how she once arrived late to a group dinner. Her friends had already consumed four bottles of wine and enjoyed their appetizers and entrees. The woman then ordered a small appetizer, one glass of wine, and had one bite of dessert – but when it came time to pay the bill, the group insisted on splitting it equally. The woman ended up paying $90…and was still annoyed with her friends eight years later.

Today, money transfer apps like Venmo, Paypal, Google Wallet, or Chase QuickPay make it much easier to split shared expenses like dinner, concert tickets, or rent precisely and efficiently. In theory, the awkwardness of not having the right amount of cash on the spot to cover one’s share is a thing of the past. But that doesn’t eliminate the etiquette pitfalls entirely. Don’t want to commit a bill-splitting faux pas that will have your friends still P.O’d at you eight years from now? Here are some suggestions for navigating common cost-sharing situations with grace.

  • Casual situations.

    • Be up front with your companions about what you are willing or plan to spend. Budgets do vary among friends, but this fact of life doesn’t have to be an impediment to group socializing. If you are matter-of-fact and unselfconscious when you state your budget, the others will likely respond similarly. Splitting the bill equally is an option as long as the smallest budget at the table is respected by all – but let’s be honest. In every group of friends, there is usually at least one big spender who is determined to splurge. In this case, having everyone pay for their own meal is the simplest, most stress-free arrangement.

Remember, it is not rude to pay only for what you had, but if this is what you plan to do, it’s polite to establish your intention up front. Setting clear expectations at the beginning of the meal is how you avoid awkwardness and friction later.

  • Splurge tactfully. Are you the person in the group who likes to spend more freely than the rest? Awesome – but you don’t want to inadvertently make the others feel small or awkward in the process. One way to splurge with grace and sensitivity: offer to treat the entire table something specific, like wine or dessert. The rest of the group can still split the rest of the bill equally, and your extra contribution will simply feel like a generous bonus.
  • Pay up on the spot. Come bill-splitting time, assign the task of divvying up the bill to the most qualified person, and then immediately act on his or her calculations. This means that if one of your companions puts the entire bill on his or her credit card, you should pay your designated share immediately by Venmo. Sure, your friend can always send you a Venmo request later, with a cute dinner emoji even, to remind you to pay up. But if you make it a habit to always pay immediately, you will never have to worry about forgetting – and accidentally becoming the Deadbeat Dinner Friend.
  • Tasting vs sharing. If you share something at dinner, expect to split the cost. “Sharing” in this case means anything more than a bite or two. So if you end up enjoying, say, half of the crème brulee your friend ordered, insist on paying for half. Bonus: if you live by this rule, you’ll avoid ingesting phantom calories (i.e. calories that “don’t count because I didn’t order it.”) Holding yourself financially accountable for whatever you eat is the responsible thing to do – your bank account and your waistline will thank you.
  • Professional situations.

    • In general, if you are selling, you (or rather your company) should pay for dinner and other costs related to the meeting. The client is effectively your guest in this situation – this is not the time to go Dutch.
    • Exception: Some clients are not allowed to let their vendors pay. If so, they will pick up the bill or allow you to pay your share. If you are the client in this case, find a way to make the situation known before it’s time to pay up.
  • Romantic situations

    • In the 21st century, whoever invites someone on a date should expect to pay.
    • However, if you accept a date, you should always be prepared to pay your half. Then, give your date the opportunity to either graciously accept or refuse your offer to pay.
    • Does splitting expenses via Venmo or other apps kill romance by being too transactional? It depends. Splitting costs too precisely, as Venmo allows you to do, can sometimes feel more businesslike than romantic. For this reason, taking turns paying for dates can be a more “romantic” solution for couples. But, as always, communication is key. Many Venmo users find that using fun emojis (of, say, an adult beverage, or a sports game) can warm up an otherwise mechanical money transfer by referencing the shared experience. “Surprise-Venmo” your sweetie with a spa day or movie night and you’re unlikely to receive complaints about lacking romance. Ultimately, it’s all about context.

The bottom line:

  1. Whatever the context – casual, professional, or romantic – always be willing and ready to pay for yourself. (It’s what grownups do!)
  2. Know which person you are, and own it. Some of us are easygoing about how we split expenses – and some of us, let’s face it, are downright OCD about tracking our expenses and payments down to the nickel. If the latter is you, embrace who you are and work with it. Be straightforward and non-defensive with your friends and significant others, and you’ll probably find that they roll quite easily with your preferences. It’s about setting clear expectations up front.
  3. Whatever the occasion, know how much you are willing to spend. This is especially important when your budget is tight. Making money decisions before any social pressure comes to bear will allow you to assert your boundaries firmly and with grace.

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