No, I’ll get it: An awkward girl’s guide to paying the bill

Photo: Dreamstime Images

You know that  pregnant moment when the bill comes to the table. I hate that moment. I get anxious. If I want to pay, I do frantic calculations in my head to ensure I can afford it. If the other person insists on paying, my stomach is equally flip-floppy because, without fail, I feel like a freeloader.

Who picks up the cheque is much more complicated than who grabs it first. It has a lot more to do with everyone’s relationship to everyone else around the table.

1) Parents and Parental Figures: This past weekend, my family gathered for brunch in honour of Father’s Day, which also happened to be my mom’s birthday. My parents typically foot the bill, no matter the occasion. “I guess you’re not going to let me pay,” my dad said. He couldn’t let the event pass without acknowledging that he felt he should pony up. My sisters and I have grown-up jobs and lives. It’s a protective guesture and I appreciate it. But they’re retiring soon, and our incomes will far exceed theirs. Besides, nobody ever wants to stumble across their parents as fans of this Facebook page.

2) Friends: I’ve had my own difficulties with this one. I’d say it’s generally safe to split the bill, unless there’s a discussion beforehand: “Hey, I know you’ve had a crummy week since you lost your job, your car got stolen, your house burned down and your partner threatened to leave you. Maybe I could take you out for dinner to cheer you up a bit?”

3) Work: Usually the company pays, but don’t assume. You’ll be embarrassed if the bill comes, and your wallet is back at the office. There is one caveat. Always, always, always say thank you to the person who signed the Visa bill (hint: the boss), and to the person who made the arrangements (hint: her or his admin assistant). I’ve heard from more than one managerial type in my social circle that  it doesn’t bode well for staff members who are ungracious about eating on the company dime.

4) Love/Dating: This, of course, is the ultimate dilema. It used to be so simple. Boy meets girl. Boy asks girl out on date. Boy pays. So much has changed. Women have increased economic power, and some men certainly resent the idea that they’re expected to pay or expect something in return if they do. (Not you of course, you’re a good guy.)

The Rules – that special old-timely book written in 1995 about how to land a man or a millionaire or something – said a women should never pay, never phone and never think for herself. (These rules apply indefinitely, btw, so they’re still good today.) But I have no definitive answer on this one.

A friend once told me whoever did the asking (also against The Rules) does the paying. It’s a good guideline (rules are for fools), but this debate remains a veritable landmine. Splitting the cheque sounds unsexy, and research suggests it’s the sign of an unfruitful date. I say avoid the issue altogether by going for a walk in the park. A dinner out is a fabricated scenario anyway that just encourages you to be the least real version of yourself. Save dinner dates for when you’re madly in love or married, or – ideally – both.

One final word of caution: beware the person (be it friend, foe, lover or leaver) who always insists on paying. It’s not necessarily an act of generosity. As Miss Manners states in this Chicago Tribune article:

There are hidden costs to relationships when one person will never consent to be treated. The surface issue of who pays covers a powerful subtext having to do with status, control, independence and connectedness.

And you thought it was just dinner.


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