I Make More Money Than Most Men—Here’s Why It Makes Dating Harder

Since my mid-20s, I’ve prided myself on being successful in my career and making good money—really good money (I’m talking well over six figures). Although I’ve worked my butt off and found great success in my career, my love life is a different story entirely. In fact, earning more money than most of the men that I’ve dated has complicated my relationships and made it difficult to find lasting love.

I never know when to disclose my income. Whenever I start dating someone new, the question of when I tell them how much I make plagues my mind. Obviously, the fact that I earn decent money isn’t exactly a secret. If he’s not completely dense, he knows that I do okay when he sees my car, my house, or my designer bag. But the question remains, when, if ever, do I specifically say that I make more money than him?

Guys Say They’re Okay with It But They’re Usually Not. Maybe at first they don’t mind the fact that I drive a nicer car or buy them more expensive gifts than they can buy me, but eventually, they can’t handle it. Initially, my ex swore that he was okay with my income and even lovingly called me his sugar mama. Fast-forward five years and it was a big part of us breaking up. If only I could tell the honest guys from the liars right from the start…

I constantly wonder whether he’s taking advantage of me. This is probably the biggest challenge I face with dating. I never know if the guys I date actually like me for me or because of the fringe benefits. Admittedly, I tend to be overly generous with whoever I’m dating—it makes me happy to see my guy happy—but it also makes me wonder whether he’s dating me for me or because I paid off his student loans and let him live with me for free.

How Generous Is Too Generous? Like I said, I like to spoil my boyfriends. I put my ex-boyfriend through school, let him live rent-free, took him on vacations, bought him a car…the list goes on. I did it because I loved him and I could afford to, and how’d he thank me? By emotionally abusing me for years and cheating on me. In retrospect, I was probably too generous but finding that balance between generosity and excessiveness is harder than it seems.

He Assumes I’ll Pay. My ex was a total jerk, but luckily, my current guy is a doll who loves me for me. However, after a year of dating, we’ve fallen into a questionable pattern—the assumption that I’m always paying. Whether it’s a nice dinner or a vacation, there’s no longer a discussion about how we will pay for it. And although I can afford to, I don’t always want to. However, like teaching an old dog new tricks, squashing this assumption is tough.

I Feel Guilty When he Pays. Most of the time, I pay for everything but once in a while, my boyfriend will surprise me by whipping out his wallet. I’m always grateful when he does but I also always end up feeling guilty knowing that he can’t really afford it, at least not like I can. This usually results in me doing something completely over the top to thank him for paying, which is not only ridiculous but probably more expensive than just paying in the first place! Stupid guilt.

We have major lifestyle differences. I may have money but I’m not a snob. That said, I do enjoy certain luxuries—I have a housekeeper, eat at nice restaurants, visit the salon regularly, drink nice wine, etc. Sadly, lots of men my age still live like they’re in college. One guy I dated refused to eat anywhere with cloth napkins, claiming they were too “bougie.” That relationship didn’t last. Men who make less money tend to be uncomfortable with my lifestyle, making me wonder, do I have to de-luxuriate my life for a guy?

I feel pressured to Maintain my Income. As if I didn’t feel enough pressure from within to maintain my income, after dating someone for a while, I also feel pressure from them. They get accustomed to the money and start to depend on it. Recently, I mentioned switching out of sales to my boyfriend. His advice? Open up your own sales office! Um, no—I want to enjoy life more and work less, thank you very much. His response just solidified his expectation for me to continue making the big bucks.

A lot of guys are REALLY insecure. No matter how big his manhood is, making less money tends to bring out a man’s insecurities. Over time, my ex claimed that my large income emasculated him. His solution? Use sex to prove his manliness. Every day, he’d throw me down and instigate rough sex. It was exhausting and it really made me examine gender roles. Traditionally, men were the breadwinners. But it’s 2017, not 1950! Roles have changed and the male mindset needs to as well.

I Want to Celebrate My Success! I didn’t inherit my money, I wasn’t given a trust fund and I didn’t win the lottery. I worked my tail off through my twenties while my friends were getting drunk and finding themselves. I earned my success and should be able to celebrate it without feeling guilty about making more money than a man. Instead, I find myself stroking the male ego and quieting insecurities. As a strong, independent, successful woman, that SUCKS. All I want is to be with someone who can genuinely celebrate my success with me. Maybe it’s time to find a man who makes more money than I do…

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