Dear Dr. Deb,

I’m newly divorced and coming to terms with single life again. I’m determined not to be a sad sack, so I make sure that I spend time going out with my friends. Some of those friends, understandably, are couples.

There’s a particular couple that I like, and we’ve kept a standing date for going out to eat. It’s been a good for me in many ways, except one: paying for the bill.

This couple routinely insists on splitting the bill 50/50 – even if there’s two of them and only one of me. At our most recent dinner they ordered two expensive meals (lobster dinners) and had four glasses of wine between them, while I had just one.

Frankly, I feel “punished” for being single. I’ve taken for granted how easier certain things can be when done as a pair. The whole situation made me feel powerless to speak up. I didn’t know how to say how I felt without sounding petty or cheap.

I feel duped, helpless, and even more angry at my ex who has left me in this situation.

Dr. Deb, what is the etiquette of splitting a dinner bill in a group with singles and couples? Until I figure this out, I might just stay home and eat leftovers.

Yours,
Punished Singleton

Dear Punished Singleton,

Ah yes, the eternal struggle of splitting the check when out with more than one friend. I feel your pain.

I’ve gone out to dinner with friends, ordered an inexpensive item on the menu, and everything’s great until the bill comes, and someone says, “Let’s just split it equally – it’s easier.”

Out come the wallets and credit cards.

Those who ordered steak or extra glasses of wine happily agree to an even split. The rest of us eye each other warily. And it can feel incredibly rude to pipe up and say, “Uh, but, um, I only had a salad and no wine.”

Although I don’t consider myself an expert on bill-splitting etiquette, dividing the bill 50/50 – unless everyone has agreed to it before ordering – is bad math. It’s especially heinous when a couple would be so inconsiderate when going out as a trio with a single friend.

But don’t worry, you’re not doomed to subsidizing your friends’ lobster dinners.

Although there really are no set rules, here’s the best thing you can do when going out with oblivious couple friends:

Speak up first. As soon as the server hands out the menus, let him know right away that you want a separate check. You don’t need to ask your friends if it’s okay. It’s not rude. You’ll be doing them a favor by making the “first move.”

As a newly single woman focused on empowering herself, get comfortable talking about money and all the things about it we were conditioned to avoid.

Advocating for yourself and needs feels awkward, but as a mature adult, good, clear communication isn’t optional. You’re not “punished” for being single. You’re punishing yourself by waiting for someone else to come and rescue you from this situation. There’s no point even thinking about your ex. He won’t be coming. No one’s coming to help you, but yourself.

Whether you’re single or in a relationship, no one truly understands what’s best for you but you. Be your own strongest ally.

Now go book that next dinner and start living your best life.

Sincerely yours,
Dr. Deb