December 10, 2021

The Real Reason Men are Scared to Date Strong, Successful & Confident Women.


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My friend Robert once said to me, “Dee, you are too much woman for most men.”

I was immediately insulted. What does that even mean, I thought?

“It’s not a bad thing. You’re smart, sassy, confident, funny, successful, and independent. It can be a little intimidating for some men.”

That was six years ago, and I’m still single. As a mom raising two young kids, dating isn’t a big priority for me. The men who have come in and dated me for periods of time are the ones that have loved and embraced all of those qualities about me. But if I’m honest, I’ve heard the “you’re a little intimidating” sentiment from more men than I care to admit like an old, scratchy record, only the lyrics sound different.

“You seem like you have your sh*t together, so I got cold feet.”

“You don’t seem like you need anybody, and a man likes to feel needed.”

“You seem really busy, so I thought you didn’t have time for me.”

“I was intimidated by your job/confidence/whatever, so I was nervous to ask you out.”

I am busy. I do have my sh*t together, and I don’t need anyone, but that doesn’t mean I don’t want someone to share parts of my life with. Also, OMG, what happened to just going out and having a good time? We’re not proposing marriage here. If being a strong, independent, smart woman makes me intimidating, then for f*ck sake, man up boys!

I went out with a guy recently who had been divorced for a number of years and brought the topic up. The ongoing joke amongst single women is that the men we want to date who find themselves single after years of marriage or being in a relationship are available for about five minutes. Only to be snatched up by women half their age (and ours).

I asked him, “What made you want to date younger women when you were first single? What’s the big attraction besides the obvious?”

“Honestly, it was just an ego boost,” he replied. “There’s nothing that boosts our ego more than knowing we can get a woman 15 years younger than us, even if we aren’t really into her. And my confidence was in the crapper after my divorce.”

Another male friend of mine offered his insight into why men will date someone younger, less accomplished career-wise, and with a little less life experience than himself or another woman he may be interested in.

“I know for myself at one time, I didn’t know what I wanted. The last thing I wanted was to date a woman who really had her life together and a lot to offer when I felt I couldn’t offer her the same.”

Some men don’t want to compete with the woman they love. One man I talked to said it sounded horrible, and he was embarrassed to admit it, but, “I don’t want to feel my partner/girlfriend outshines me financially or career-wise. That’s a real boner killer right there. Honestly, I’ve had issues in the bedroom with women who were more successful than me.”

Some men I spoke with admitted that they see a woman who exudes confidence, success, and a strong sense of self and immediately feel she’s out of their league. They may want to ask us out, but they psyche themselves out before they get there.

One man shared that, in the past, when he’s met or dated a confident, successful, the-full-package kind of woman, he was scared sh*tless he would let her down. “I’d think to myself, ‘What if I lost my job or didn’t make enough money? What if I can’t give her 10 orgasms a night?’ The pressure I felt, honestly, was stupid. I never felt this way dating women who were younger and not as successful as me, so I just found myself dating those women instead of the ones I really wanted to be with.”


Guys, I’m here to tell you, you’re missing out.

And ladies, I’m here to tell you, you’re not.

If you’re a man who can relate to any of what I’m saying here, please know that we like you not because of your income, job title, or level of success. We see something deeper in you that unfortunately you may not see.

Ladies, you should want a partner who can meet you where you’re at. You should be on the lookout for someone who finds your success an inspiration, not a barometer to measure their own worth. If they don’t feel worthy of a woman like you, they’ll eventually sabotage the relationship because that’s what people do when they don’t feel worthy of something.

We can’t convince someone of their “enough-ness” nor can we do their inner work for them.

So, as a woman who has worked hard to develop a strong sense of self in the world, a healthy self-esteem, and pride in my work and personal successes in life, I’m okay waiting for a man who doesn’t find that in the least bit intimidating.

And I hope for those men out there intimidated by women like myself that you realize your own self-worth so you don’t miss out on being with a someone who might be a great partner for you.


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