The Dating Question That Perplexes Us All


I still remember the day my college roommate was set to go out with her now-serious boyfriend for the first time. They had plans to “hang out,” and Maggie wasn’t even sure if it was officially a date, much less if she would be expected to pay. Two years and a lot of dates later, Maggie (an adamant feminist) says she and Jared still don’t have a consistent rule for handling their going-out finances.

It starts as soon as someone makes that first exciting (and terrifying) move. You’ve been exchanging witty banter with that Bumble hottie for a solid week now, and it’s time to take your relationship past the barriers of cyberspace. But the excitement is sometimes quelled by a nagging question: Who’s going to pay, and will it be awkward when the check arrives?



Regardless of whether or not you want or expect a man to pay every time, there may inevitably be times that he doesn’t want to.



It used to be pretty typical for a man to pay for a first date and the subsequent courtship without question. But these days, all “rules” are out the window — you, as a woman, might make more money, you might have been the one to initiate the date, or you might have picked the place. Your date might not even be with a man at all. With all there is to consider, it’s borderline impossible to know what to expect when it comes to the financial aspects of the beginning stages of a relationship. To prepare yourself, it’s best to have a ready-made plan in place to avoid finding yourself in an awkward situation — or, even worse, a situation you aren’t financially prepared to handle.


Self-awareness is key.

I have a friend who feels disrespected when a man assumes he will be paying for a date. I have another friend who feels disrespected when a man doesn’t assume he will be paying. There are no right or wrong answers here, but there are things that will feel right or wrong to each individual person.  Additionally, your own intentions for the date can dictate how to handle each individual situation. If, say, you’re already anticipating there won’t be a follow-up, you may want to consider splitting the bill to make your intentions (or lack thereof) perfectly clear. Or if you want your partner to know how invested you are, you may want to go into the date with the intention of paying. Be open with yourself to decide what makes you most comfortable, and stick to it.


Know your own financial boundaries.

Regardless of whether or not you want or expect a man to pay every time, there may inevitably be times that he doesn’t want to. In that case, it’s obviously important to understand what you are personally comfortable spending. If you genuinely aren’t sure who will be paying for an outing, make sure it’s not taking place anywhere outside of your own price range. It’s best to never assume one way or another, so make sure you’re prepared to foot the bill if it comes to it (or if you want to!). Personally, I like to know a date’s location and price range before I even agree to it, if only for my own financial peace of mind. A quick Google search for a place’s menu can help you decide!



The person on the other side of the table is a human being just like you are.



Participate in open communication.

As awkward as it can often be, it’s important to just be honest with one another in regards to expectations. If feminism teaches us anything, it’s that you have the right to speak up for yourself in any and all situations. Another friend of mine, Danae, was recently asked on a first date, and her date suggested a very expensive restaurant. Danae then suggested a different option with a lower price range, and she was ultimately glad she did. This way, she was prepared to pay if need be, but she also didn’t feel guilty when her date ended up footing the bill. If the relationship is going somewhere, you’ll be glad you opened the door to open communication early on.


Above all, be gracious and enjoy.

Dates are supposed to be fun! Don’t let the stresses of potential financial awkwardness get in the way of the enjoyment of getting to know a new person. Overall, it’s simple: Know your own boundaries and limitations, be gracious either way, and have a nice time. The person on the other side of the table is a human being just like you are — and they might be one you end up really loving! Maggie and Jared told me that they can’t remember which of them paid more often in the beginning of their relationship, but they do remember that those dates laid the foundation for the happy and loving relationship they have now.

What’s your best advice for navigating the first-date financial situation? Do you reach for the check? Let us know in the comments!