The Money Questions I Always Ask On The First Date

By | Friday, June 17, 2016


In my dense (and very, very stupid) dating past, I have never paid any mind to money. I have worked very regularly and very hard since the day I was of legal age to do so, and never found myself any more impressed by the money of any man than I was by my own financial situation. For that reason alone, money was never something on my radar when seeking a partner. It was never a topic of discussion, an issue, or really even a thought. This also is due largely in part to the fact that I’m very young, so most of the men I’ve dated hardly had a financial life to speak of. The ones who did, however, are the reason why this time around, I’m making money a part of the discussion.


I’ve only recently entered back into the dating world, and upon being asked more than once what my criteria are for finding a new significant other, I’ve responded with some variation of “ummm… he has to shower regularly.” Clearly, I haven’t exactly been spoiled by my boyfriends.

A guy I recently dated was – for lack of a better phrase – weird as fuck about money. He squirreled it away and wouldn’t dare spend it on buying us dinner, but boasted a sweet collection of superhero action figures, some of which he spent his ~very important~ income on, and some of which were purchased by me as gifts for him. (I will forever hate myself for that.) The boyfriend before that had no money, car, or job – so I played “what’s mine is yours, sweetie!” and wasted a huge chunk of gas money and other cash treating him to the life I thought he deserved. (Ah, young love!) During these relationships, my bank account was startlingly low, and I found myself constantly anxious about whether or not I could afford the small things I wanted or needed because I was spending too much trying to win the love of a shitty boyfriend.

This week, however, I looked at my checking account and was shocked to see that the number was double the number it usually hovers around. As I scrolled through the statement trying to see what exactly I had done to save that much money this month, I realized something absurd – the only thing that changed was my relationship status. In the months since my last relationship ended, I’ve saved an estimated $800 on shit that I was mindlessly spending it on in the name of romance. All of the dinners I treated him to because I knew if I didn’t, we wouldn’t eat. All of the Dunkin’ Donuts card swipes buying coffee in the morning when I stayed at his place because he didn’t have a coffeemaker. All of the “just because” gifts I grabbed for him here or there, knowing the gesture would never be returned. Apparently my life, minus all of those things, is a much wealthier one (financially and emotionally speaking).



This time around, it is absolutely essential that I do something differently. I refuse to try to make a worthy mate of a financial disaster again – my bank account simply can’t handle it, and quite frankly, neither can my heart. It isn’t exactly foreplay to message a handsome Tinder boy and ask him about what kind of financial situation he’s in, but damn if that isn’t exactly how I’m going about this. I’m determined not to get screwed over again.


And it isn’t about getting taken care of, or treated. I am very, very much a feminist, but I don’t think that picking up the check myself, or allowing my male date to, is an issue of feminism versus anti-feminism. To me, the decision to do something nice for a person I care about is a genderless one, and I firmly believe that those types of kind gestures should happen on both sides of a relationship, financial status permitting. When I’ve dated people who had a little less cash then I did, I never minded paying the check when we went out. When I’ve dated people who had money, but didn’t think I was special enough to spend any of it on, it just made me feel like shit.


There is this really corny Tumblr-y picture I see shared a lot on my Facebook timeline that says something about how if someone has a million dollars and gives you a hundred, it isn’t as meaningful as someone who gives you ten dollars when they only have ten. This is not my way of saying I expect the new men I date to give me all of their dollars. But I am saying that, rather than trying to figure out how much money they have, how much debt they’re in, or how much they’ll one day be worth, I am asking them about their financial habits. If they’re in debt, is it because they have a dumb habit of buying old sports cars, or is it because they took out loans for school? If they live with their parents, is it because they are financial nightmares, or are they being smart and staying there while working towards a savings goal? If we were out one night and I was thirsty, would they offer to buy me lemonade, or would their hide their money in an aggressively large savings account and act poor so I’ll buy them stuff?



The point is, I want the men in my life, from this point on, to talk with me about money. I want them to know my goals, my habits, and what I value spending money on (especially because one of those things will likely be them). And I want to know theirs! I want to know what kind of debt they have, what kind of future they are planning, and where they like to put their money. I want to know that we are, in some way, financially compatible. I want to know that I’m going to be treated like a person, maybe someday a girlfriend, and maybe someday even a wife, rather than like a sugar daddy. I will never mind paying for dinner, or buying a “just because” gift, as long as I always know that I’m not being taken advantage of and used for that money, as I definitely have been in the past.

This has only been a practice of mine for a short while, and I’ve gotten mixed responses from my dates. If anything, it is at least helping me weed out potential bums and abusers before the waitress even takes our drink order. Secretive about your financial situation? Pass. No attempt to offer to pay? Pass. Deeply in debt, but still happily jobless? Pass.

At the end of the day, I still have no hard-and-fast rules or specific criteria to go by as I continue my dating journey. But opening up the conversation about money early, being honest about what I’ve had, what I now have, and what I want, is one of the ways I plan to halt any financial abuse before it begins.


Mary is the summer Media Fellow at The Financial Diet. Send her your summer intern stories (your lessons, failures, triumphs and good advice) at

Image via Pixabay

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