Picking Up The Check In 2018: Who Should Pay?

Photo by rawpixel on Unsplash


There’s just no simple answer to the question “Who should pick up the check?” First of all, “the guy should pay” doesn’t really help when two women or two men are on a date together. As high earning Millennials, we are re-writing the playbook on almost every outdated tradition and this one is no different. Besides, what about all of you ladies bringing home way more bacon than your man? Is it still on him to foot the bill for a splurge at The French Laundry or Per Se?


The old, and very tired, tradition of the man picking up the check at the end of a date is so 20th century. We’re ready for a more nuanced, thoughtful response to this very real, and very sensitive question.


A few things to consider:


Who initiated the date?

A good 21st century rule of thumb can be letting the person who initiated the date pick up the check. This takes gender out of the equation, and can also help with how to trade off treating each other.


Who makes more money?

If there is an imbalance in finances in your relationship, it might be a good arrangement to let the person with more cash to spare pick up the check (particularly if Michelin stars are involved) and save pizza runs and movie tickets for the less affluent dater. It can be great to have a conversation about what kind of dates you each can afford, and you pick up the check for the types of activities that won’t break your bank. That way you both get to feel like you’re treating each other.


Your personal money history with your date.

Do you and your date have a history of them picking up the check? Might be a great opportunity for you to flip the script. Or it could just be business as usual.


Well, should we just split it?

Maybe, but maybe not. If one of you has planned the date it can be tricky to expect the other person to split the bill of an evening you orchestrated. This can be particularly messy early in a relationship. Splitting the check can be great, but make sure it isn’t undermining the romance of the moment or ignoring the financial reality of the person you’re out with.  If you’ve suggested somewhere pricey, don’t always expect your date can throw down the same way you can.

Talking money on a date can actually be a great idea, no really.

And if your date is treating you to a romantic night out, don’t ruin the moment in the name of ‘fairness.’



How do I get my date to pick up the check if I usually do?

Ask them to. We know, talking about money can be tricky, but if you’re dating someone it can be really important to have some tough money conversations. If someday you might be discussing joint checking accounts, down payments, or even college funds for your kids, “Do you mind picking up the check this evening?” can be a great place to start having those basic money conversations.


Let’s talk about the fake wallet reach.

You may be familiar with this move. You know your date is probably going to pick up the check, but you don’t want them to think you’re cheap, or unwilling to pitch in, so you reach for your wallet, but you both know your date is going to intercept you before you get there.


We propose saying goodbye to the fake wallet reach. Real wallet reaches: totally fine. But only reach for your card if you’re willing to put it down.



Am I a bad feminist if I want my date to pick up the check?

Nope! Wanting someone else to treat you isn’t an ethical or moral issue. You want them to value the time they spend with you. And that’s what picking up the check can be, a valuation of time spent. That being said, if you’re relying on your date to always pay the bill, it might be good to check in with them that they’re comfortable doing this so it doesn’t become a source or resentment down the line.


Talking money on a date can actually be a great idea, no really.


Our best advice is to take this as an opportunity to learn to talk about money with the people you date. This doesn’t mean you need to compare salaries on your first date, but it does mean that you take responsibility for showing the people in your life that being responsible with money is one of your priorities. You’re taking your finances seriously, you’re a H.E.N.R.Y.™. That financial maturity doesn’t stop when you swipe.


SHOWHIDE Comments (3)
  1. Guys only appreciate what they have to earn and invest in. If you pay on the first date, most likely he will be gone after the 3rd one, right after you offer yourself up to him in order to be “so 21st century”. Have some sense of self- worth and self-respect ladies and spend that first date money to treat yourself.

Leave a Reply

Your email address will not be published.

The F Word