How I Fell In Love With A Sugar Mama

She made more money than me, and I loved her anyways.

Last updated on Jul 06, 2023

rich attractive girlfriend pulling down sunglasses Stas Ponomarencko / Shutterstock

When I was working as an English professor, my fiancée ran a medium-sized company and made 15 times as much money per year as I did — before her bonus. Like many men, I'm proud and competitive. I had already accepted that I wasn't going to earn more in my life than my father.

Now I blanched when I wanted to take my darling to dinner: would we go to the kind of place she's used to, which I couldn't come close to affording, or would she be willing to slum it with me again?


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Ultimately, she and I came to a very amicable agreement on spending: we'd alternate who paid for what, and, yes, she'd take me to fancy places and I'd take her for pizza. To her credit, she never complained about picking up bills or paying part of my way if we went on a nice vacation.

We were only together for two years, though, and I wonder if — over time — the differences in our lifestyles would have gotten to her... or to me. I like to think they wouldn't have, even though the chivalrous part of me would always wince when she took out her wallet. 


My guy friends didn't seem too worried about chivalry; they just asked if I was intimidated that she made so much bank.

On this front, I'm happy to say no. Actually, I was proud of her — really proud. When I would travel with her on business and she'd be on the phone yelling at her (mostly male) team at 3 a.m., I'd take a few of the very lush Ritz-Carlton pillows and go sleep in the tub, smiling at how formidable she was. 

I think that a good relationship is one where both the man and the woman can teach each other things, where they alternate leadership, have mutual respect and are each truly impressed by what the other one says and does.

Insecure guys are, of course, famous for wanting to date women who don't challenge them — whether they're younger, meeker, less intelligent, or make less money. But where's the fun — and the long-term excitement — in that?


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The trick, I think, for a successful woman trying to date a "less successful" guy (read: he makes less money or has less education) is not to make him feel that way. My ex always praised both me and my career, saying, "What's money compared to the books you read and the thoughts you get to have?"

She also didn't bring her management strategy home from the office. Both genders can learn from that: the same skills that make you very effective at your job or in school might actually be damaging when used in a love relationship. At-home leadership is typically much more about humility, compromise, and cooperation — not always the strong suits of type-A people. 

As for guys, we need to abandon the myth that we should be making more than women (or our fathers).


We should be impressed by the success women achieve, not intimidated.

Granted, it used to be hard for me to meet my ex's male business colleagues and have to admit that I was a literature professor at a small university but, really, that was just my own insecurity speaking. I wish I'd been thinking, "I'm the guy that your powerful female co-worker has chosen to be with, so you can only imagine what I've done to win her over." The very fact that you're the one she's with validates you, and you should just bask in the implicit praise. 

I will confess one more weakness: when I was planning to ask her to marry me, I lay awake at night imagining the wealthy guys she interacted with all day looking at her engagement ring, and wondered what they would think if I gave her one that I could actually afford.

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So I took advantage of my free time and did a ton of research, designed the ring myself, spent months looking for the perfect (huge) stone, and finally spent half a year's salary on the thing.

Yes, I was being insecure and competitive; no, it shouldn't have mattered that much; and, yes, that was a ton of money for me to spend. But I have to say that it proved worth it when, at one of her work events, her CEO saw the ring and said to me, "Quite stunning. Did you get it at Bulgari?"

As men, we can't always be who we'd like to be; we just have to do the best we can.

Here are 4 tips for dating a man who makes less money:

1. Find something about him that makes you proud, and tell him about it—often

2. Leave your office persona in the office

You don't manage him, and if you act like you do, you'll make it harder on both of you


3. Be sensitive to the fact that he makes less money

What may seem like a reasonable price to pay for dinner could be a huge splurge for him

4. Address the inequality directly, and figure out a solution that you're both comfortable with

Maybe you pay for the fancy dinners and he pays for takeout. Or perhaps he pays for everything in public and you pay for the things you do in private.

If you're still getting to know him, accept that until you're comfortable addressing the inequality directly, you might have to eat at mid-range or inexpensive restaurants and generally live a less expensive lifestyle for a while


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John Keith is a freelance writer and former contributor to YourTango who writes about love, romance, and how to find it.