Welcome back to Uncomfortable Conversations About Money, a new series where we will tackle topics or situations around money that make you uneasy. We'll outline the problem and try to get you some usable solutions.  

Today's topic: How to handle that uncomfortable conversation when you’ve gone out with friends and not ordered as much – but they want to split the bill evenly.  

What should you do when diners overindulge, then want to split bill?

The dilemma: Alan Kalinsky and his wife, Sandy, go out to eat a lot with friends in Los Angeles, where they live, and recently in Boca Raton, Florida, when they were on vacation.

Kalinsky, a retired Rabbi, jokes about it now, but there was one time, about 20 years ago when one of those outings was a lot less enjoyable.

Two couples, whom the Kalinskys didn't know well, ordered duck – the most expensive item on the kosher menu. 

When it came time to pay the bill, the duck couples suggested splitting the bill. 

“That meant I paid for their duck,” said Kalinsky, a USA TODAY reader who responded to our query about the subject. “We were much younger and struggling to pay our monthly bills, let alone eat at a fancy restaurant.”

The Kalinskys bit the bullet and paid for the meal, but it left a bad taste in their mouth. Years later, they now laugh about it, and even refer to the other couples, whom they occasionally still see, as Mr. and Mrs. Duck. 

“We just didn’t want to make waves that night, but it would’ve been the right thing,” Kalinsky said. 

Since then, the Kalinskys have learned to tackle that particular uncomfortable conversation early or even before dinner.

Their key piece of advice? Communicate with the people who have invited you and if you’re on a tight budget, don’t be afraid to say that, Alan Kalinsky said. Also, establish if one couple is up for treating the other.

Another reader responded to the check-splitting dilemma with a more egregious scenario.

She and another single friend went to dinner with a couple.

"We all ordered drinks and the couple ordered a ton of food for us all to share, plus the husband ordered his own entree – a steak," said the woman, who asked not to be identified.

She didn't like much of what was ordered, but figured she could find something to "pick at."

"We enjoyed the meal and drinks and when the check came, the husband said to the server 'you can split the bill three ways' – and he counted he and his wife as 'one person' plus each of us single women. They ate the bulk of the food (and his own entree) and drank more than each of us single ladies."

Her portion of the check? $258.

"That just didn't seem fair at all. But I kept my mouth shut and paid my portion... and I've been stewing over it ever since," she said. "Should I have said something? Now, I kind of wish I had, but they are good friends and I didn't want to rock the boat."

Tackle the uncomfortable conversation early to establish bill payment

The expert advice: “People do not like to have this uncomfortable conversation,” said Elaine Swann, a lifestyle and etiquette coach in Carlsbad, California, and founder of The Swann School of Protocol.

“But you have to,” she said. “My recommendation is to embrace the awkward. Find out who’s paying for what.” 

Do it early – preferably before you accept the invitation to go out to eat, said Swann. Take a look at the menu and see if it’s something in your budget and then ask if people will be splitting the tab or paying on their own, she said. 

Or address it as soon as you sit down for the meal. 

“Then if you know you’re paying your own way, then honey, have a way. Have the bottle of wine, have the appetizers, have the duck and whatever you want,” said Swann.  

“I like to say exchange momentary displeasure for long-term hassle,” she added. “Once you find that out, then you can really enjoy your dining experience.” 

Here are some more tips for that uncomfortable conversation

But what should you do if you didn’t have that conversation early on and now you’re in that awkward moment when others are expecting you to split the bill evenly? 

Swann recommends discreetly trying to talk to the person at the table who coordinated the dinner and explain that you prefer to pay separately. Or tell the server you want to pay separately. 

If others aren’t accepting of you paying separately, then you’ll probably have to keep the peace and grin and bear it – then make sure you find out next time before you accept an invitation with this group, what the bill-paying plan will be, said Swann. 

From an etiquette perspective, Swann said it is fine to ask people not to split the bill evenly, unless you’re in a higher-end dining experience, such as a private dining room or at a chef’s table. For a more exclusive experience, it is proper to split the bill evenly, she said. 

It used to be gauche to talk about money and budgets, but it is OK to bring it up when accepting an invite to eat out. It’s also OK to decline the invitation if you can’t afford it, she said. 

Want to be featured in our next Uncomfortable Conversation? 

Our next topic: These days, being a bridesmaid or groomsman in a wedding can get very expensive, especially if the ceremony and the prenuptial festivities are out of town, adding even more costs on top of the bridal party attire and other expenses. Can or should you turn down an invitation to stand beside your friend at the altar?

If you have been in this situation, how did you handle it? Did you take the hit on your wallet, or bow out? We'd like to hear from you.

Do you have an Uncomfortable Conversations about Money topic you'd like to suggest? Or would you be willing to be featured in a future story about your Uncomfortable Conversation? Email [email protected] with "Uncomfortable Conversations" in the subject line. 

Betty Lin-Fisher is a consumer reporter for USA TODAY. Reach her at [email protected] or follow her on X, Facebook, or Instagram @blinfisher. Sign up for our free The Daily Money newsletter, which will include consumer news on Fridays, here.