Ask Polly: Men Are Too Intimidated to Date Me!

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Dear Polly,

I’ve recently had a man, who I’ve known a long time and had a series of false starts with, whisper my greatest fear: He won’t date me because he’s too intimidated by me.

Literally. “I really, really want to date you, but I’m too intimidated.”

He’s a shitheel, and I’m better off without him, but this one sentence keep echoing because it matches the story that not only have I been telling myself for years, but that my family, and friends, and the culture at large tells us: intelligent, capable women who talk about how they feel and what they want scare the crap out of men.

I want to say that this is of course only some men. Weak men. Insecure men. But there’s a tiny whine in my brain that goes … “No. It’s all men.”

My go-to Anxiety Time move is to make the personal Political, the micro Macro. So it’s not just This Dude, it’s The President, it’s Men Today or Men Always.

It doesn’t help when my brothers, my father, married women I know, single women, all just sort of shrug and go, “It’s distasteful, but true.”

Which feels shitty! I love the men in my life, including when they say, “You’re great, but you’re going to need a special kind of man.” or “You have to admit: You’re a homeowner, you’ve got a good career in a glamorous business, and you know who you are. Most men don’t know what to do with that.”

I don’t want to resent men for owning up to their own feelings of insecurity — after all, they’re hurt by this cesspool of misogyny, too.


I resent men for owning up to their feelings of insecurity!

That seems like a pretty dark corner to be in. My instincts say I should have empathy, but my volcano brain says: Why on earth should I have to hand-hold another grown adult through acceptance of my awesomeness? I just want to be an awesome, messy, wonderful, horrible person alongside someone else doing their version of being awesome, messy, wonderful, and horrible?

Maybe that includes being intimidated? But that’s so fucked!



Dear Resentful,

Resentfully believing that men are too intimidated to date you is 100 percent of your problem. It puts a script in a guy’s hand before you’ve even seen him clearly, the same way that you claim that merely being attractive, successful, and clear about your desires makes it impossible for men to see you. It’s downright dehumanizing to a man you don’t know for you to enter the interaction assuming that he’s so fucking weak that he can’t handle a beautiful, confident woman who knows her own mind and heart. As long as your contact with men is clouded by this assumption, you’ll be subconsciously blocking them from getting to know you as a real live human being. You’ll think that you’re smoothly presenting your best self or whatever the hell, but underneath that smooth exterior there will be a conflicted, roiling, angry sea of premature assumptions about who you are (great, rejected) and who he is (afraid, weak, rejecting) and how it will all play out (crash and burn).

Having empathy for a man you assume is shivering in your presence is not the answer. You’re still sure that he’s afraid of you, the poor fuck. You still think you know everything about him before he’s opened his mouth. And so everything he does will fall neatly in line with your script. You seem suspicious. This makes him nervous. He fumbles with his words. You think, “Fuck, it’s happening again.” He thinks, “She seems pretty great, but why is she already pissed at me?”

And no wonder you’re angry. You’re so sure that everything amazing about you turns men off. You’ve worked so hard to get here, to be a success, to look decent, to own your own place, but romantically, you feel like you’re being handed a giant shit sandwich for your efforts.

I’ve always hated this story about how smart, successful, direct women are scary to men. To me, this is one of our culture’s deeply inaccurate gendered stories, like “Men always want to fuck random women and basically need to be tricked into marrying someone, but they’ll never really be satisfied sexually by one person.” I mean, what could be more poisonous for a guy than to walk around assuming that a totally normal thing that a lot of people do — pair up! — doesn’t suit his essential nature and will only make him miserable? It’s pretty fucking hard to be happy when your culture informs you at every turn that your happiness is an impossibility. “You’re not like her,” it whispers in your brain. “You want to fuck everything you see.” Um, newsflash: Some small part of all animal brains wants to fuck everything it sees and eat everything it sees and sleep half the day. That doesn’t mean we’re incapable of being satisfied spending our life in pairs, tuning into each other emotionally, living together, cooperating, and, yes, ACTIVELY SEEKING TO SATISFY EACH OTHER.

Besides, I don’t buy it. I don’t believe that men are such abject losers that they can’t bear to be in the company of great women. Most of the men I know would leap out of their skin with joy at meeting a woman who’s hot and smart and has an established career and asks for what she wants directly. I don’t believe that the men I know well are an exception to the rule. But I do think that most people walk around parroting the same idiotic cultural assumptions because the alternative — observing the world closely and coming to your own conclusions — requires way too much work. Fuck, most people don’t want to decide between the chili cheese fries and the patty melt, let alone pay attention and come up with a unique thesis about the humans around them in the absence of a cultural cheat sheet.

The fact that everyone you know is telling you the same goddamn thing says more about this tendency than it does about the way the world works. These people are the ones who are afraid to give an original answer, like, say, “You’re really fucking bossy sometimes,” or “You come straight out of the gate acting like a guy owes you something.” They’re seeing something about you that’s probably off-putting at the outset, but since they don’t want to get into the specifics of that with you, they just use the closest proximal one-size-fits-all dipshitty cultural cliché and package their real feelings inside of that, leaving them and you blameless.

You’re going to assume here that I mean you’re an overbearing woman just because you’re successful. You’ll assume that I’m adding you up and coming up with a negative stereotype of you. Au contraire! What I’m saying is that you are PREEMPTIVELY CONFLICTED about men because you hate this message you’ve heard all your life and you also hate feeling vulnerable. You have kicked ass and taken names for years and now you’re supposed to ACT LIKE YOU’RE LESS THAN YOU ARE just to get a man. But in reaction to that, you’re entering into situations feeling conflicted and pissy and making assumptions that a guy is less than he is. Being conflicted under the circumstances is perfectly fine and understandable, mind you. But your friends and family sense this conflict and instead of understanding the layers of it and reminding you of who you really are and telling you, “Don’t worry, someone will see you and love you like crazy,” they think, “She is pretty bossy” and “She is kind of a steamroller” and then they grab for that old trope “MEN HATE AMAZING INTIMIDATING SUCCESSFUL WOMEN. IT’S TRUE! IT’S NOT YOUR FAULT!”

Generally speaking, if you ask a gendered question, you’ll get a gendered answer. Everybody loves to repeat the same old gendered tropes to each other. And as long as you’re going against the grain, gender-wise, the whole world is going to believe that you’re doing it wrong. All of the gendered bullshit they carry around with them that controls their behavior gets in the way of being able to formulate an objective answer. It’s like asking a hungry lion if he likes your new manicure. Yes he likes it, he’ll say, because it smells like meat.

Here’s the truth that even people who are prone to repeating stupid cultural clichés know in their hearts: At one level, yes, people are controlled by the deeply stupid messages they carry around about who they are, based on who the culture has told them that they are. They see a tall, good-looking, successful woman and they say, “SCARY because me man and man scared of great woman!”

But at another, deeper level: People see each other clearly. They see each other’s true desires and fears. They know when someone is afraid, and when someone is conflicted, and when someone is pretending. They know when someone is suspicious or annoyed or sure that nothing will ever work out. They know when someone is willing to fuck but wants more. They know when someone is willing to date but really just wants to fuck. And they know when someone is too anxious to see them at all.

You are the one who is afraid. You’re afraid of being seen clearly. You want everyone to see that you are beautiful and successful and amazing. Even though you say that you are awesome, messy, wonderful, and horrible, you can’t quite live out in the open with your awesome messy wonderful horribleness yet, or you wouldn’t be asking other people what men really want. If you were okay with being scared and weak sometimes, you would know that it doesn’t matter what all men or most men want. You would know that you can invent the whole world with a man who gets it, and it won’t fucking matter what anyone else thinks about how scared or weak or messy or horrible or intimidating you are. Neither of you will give a fuck how the whole world thinks you should be simply because you’re a woman. If you weren’t so afraid, you wouldn’t walk around telling this story about how all rejection must boil down to men being afraid of you. You would be open to showing up without jumping to quick conclusions.

People who are afraid of their feelings like to tell very clear, sad, predictable stories to explain everything that’s happened and everything that’s going to happen. People who are afraid of their feelings are everywhere. Fear them. But don’t fear men. Don’t fear rejection. Don’t fear your own messiness and your own awesomeness. Every single trait you carry around is not a predictor of whether or not you’ll find love. You don’t need to read a census report to understand what happens next. You need to accept the fact that you don’t know what happens next.

You don’t know. You are afraid.

If you really want to be seen clearly, show up without retreating to the safety of your assumptions. Show up and listen. Show up and admit, “I am amazing and I am also horrible.” Show up and say, “I have done everything I set out to do, but this love thing scares the living hell out of me.” Show up and say, “I’m afraid of what comes next.”

You already know that you don’t want a man who is clearly intimidated by you. That’s good to know. You don’t want that feeling of someone being afraid of you, when you’re not scary at all. That feeling of scaring people is the saddest, loneliest thing for you, because you’ve felt it all your life. But in order to stop feeling that way, you have to be okay with not being scary at all. Are you okay with not scaring people? Can you just be another person in the room, like everyone else, not necessarily all that impressive, a little bit conflicted, a little bit worried about being rejected again? Or would you rather stay scary and safe, and retreat safely to the same old story about What Always Happens Next?

Either way, here is the truth: You don’t know what happens next. As scary as that is, it’s also beautiful and electrifying and exactly how it should be. Savor it.


Order the new Ask Polly book, How to Be a Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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Ask Polly: Men Are Too Intimidated to Date Me!