The Real Reason I Don’t Date Men With Money

Are they hiding something?

Of course, I want to date a man who has enough money to take care of himself (and this of course includes any responsibilities or obligations he might have to his children and family, property, or career). Of course, I want to date a man who can pay his own way, pay for both of us at least half of the time or whenever he feels called to open his wallet. And of course, I want to date a man who indulges in the kinds of things that I like to splurge on, like vacations, thoughtful gifts, tickets to shows, and weekend trips away. But money or not, it has to be worth my time. 

Women spend twice as much time as men, on average, on childcare and household work, having 13 percent less free time than men, according to a 2022 survey. Another survey from the following year says that two-thirds of women over 40 spend less than five hours a week on their own hobbies and self-care. I wouldn’t be surprised if that figure has gone up, given how we are all morphing into Wonder Women, doing the work of men, plus, plus. 

Now that I am an empty nester with my own business, I’m fiercely protective of the free time that I have. I finally have a lifestyle that allows me to do what I want when I’m not working, and I happily say “no thanks” to anything that doesn’t appeal to me. If I want to stay home in my nightgown and get in bed at 8:30, rewatching The Sopranos with my dog all winter long, that’s my choice. If I want to stay up until 2 a.m., reorganizing my pots and pans, playing drums, or pulling Tarot cards, so be it.

This is in fact the winter agenda I’m very much committed to, so going on dates is taking a backseat to self-care at the moment. If I do go out with someone? Well, dazzle me with something other than cash; showing me you’re some kind of big shot will not motivate me to take off my fuzzy socks.

I do know plenty of women my age—also single and living alone—who are looking towards their next chapter and feeling like they don’t have enough money to make it to retirement without a partner of means. That’s probably me too. I more than get by, but it sure would be easier if I had someone with a hefty bank account to help out. But as much as I’ve attempted to talk myself into it as I age, I know that, for me, a big wallet will never make up for a big thrill in bed.

Sure, over the last couple years, I’ve dated men who were well off, generous with money, and didn’t make it into their entire MO. But I’m talking about the men who make their financial cushion a selling point. I’m talking about the guys who make sure you know what kind of car they drive even before you go on a first date, who tell you about their family tradition of St. Barts at Christmas, or who seem to always have at least a few hundreds in their wallet. Perhaps it’s me, but eight times out of 10, these guys are waving their finances in your face because they think it legitimizes their desirability. I’m here to say: Nope. It does not. 

Last month, I met a real estate guy in the Hudson Valley where I live. He’s a mover and shaker. I like that. He loves what he does. I like that, too. He has impeccable manners and wouldn’t let me pay for a thing. But it wasn’t long before I got the message loud and clear: He was boring as hell.

He was intent on talking about all the deals he was making and even though he did ask me some questions about myself, they were mostly focused on how my own business was going. He also had a maddening habit of referring to me as “Young Lady,” even though I told him pretty damn quickly that I found it weird as hell (he was only a few years older than me). But he kept “Young Lady-ing” away as he waved off my attempt to buy us dinner on our second (and what I knew would be our last) date. Then I did something that I’ve never done in my life…I ghosted him. 

This guy was handsome, he lived a fairly adventurous life, and I can think of a dozen subjects that he dangled in front of me which might have piqued my interest, had he wanted to go into any of them. He did not. It seemed his in-your-face money thing was perhaps an attempt to cover up something else (you knew this was coming, right?)…like a non-working penis.

You probably have girlfriends who will find my POV utterly horrifying, because for them, a guy who wants to pick up the check all the time and only wants sex on the rare occasion is a big plus. Plenty of women have moved into their menopause years with quelled sex drives, so a less frequent fuck is appealing. I’m not that woman. 

This past year, I went on dates with several Masters of the Universe, all pumped to whip out their wallets. I never got past a chaste kiss good night from Mr. Real Estate. But there was one or two other men who advanced to the semi-finals, while I tried to figure out if I was truly interested or if the fact that they looked good “on paper” was keeping me in the conversation. Plenty of women I know (you know them too) were saying, “He seems like a great guy and so generous! Isn’t it nice to have someone want to take care of things?”

And while yes, that is nice. And while yes, I’ve taken care of things for far too long on my own, it still doesn’t mask the reality that a bank account doesn’t turn me on in bed, doesn’t make my heart race, doesn’t keep me warm at night. 

One of the Masters from this past summer was a truly lovely man, and besides showing me his Platinum card, he showed me considerable sweetness. He was a champion hand-holder and back-rubber. He talked to me about the kinds of vacations we could take together in a way that showed me he put some real thought into what we’d both enjoy. 

But as we spent more time together—and I told myself to give this a chance—something felt inorganic. I was trying to talk myself into a long-term romance with him but the flow was off. Once we went to bed together, I knew right away that my intuition was correct. He had Erectile Dysfunction (which is workable if you bring your partner into the mix and agree to take a pill or similar) and he didn’t want to talk about it. He just kept saying, “But we have so much to enjoy together and so much in common! Give us a chance!” 

We did have a lot in common and we were having a good time; it was clear he had plenty of money for us to continue doing whatever we wanted. But I wanted something else and no amount of cash was going to bring that into the mix. 

Let me be really clear. Do I think that all men with money are sexless or using their cash to overcome what is lacking in other areas of their life? Of course, no. But offering the alluring sweetheart deal of a “comfortable” life is something that men often dangle in front of women our age, and to this I say, this sweetheart isn’t buying it. 

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