Dear Polly,

First of all, let me assure you, I feel like a huge asshole just for asking this, but I’ve been chewing on this question on and off for more than a year without any real resolution, so I thought I’d turn to you. Here’s the deal: I’m wondering whether I’m abusing feminist ideology in order to justify a natural shyness around women and, if so, whether you could find me a new narrative that would help me feel less bad about acknowledging and acting on attractions.

I’ve always been seriously shy about any aspect of dating, sex, hooking up, whatever. It’s not that I have trouble interacting with women — indeed, my female friends greatly outnumber my male friends. I have no problem making friends with women and, in general, I feel I am generally more comfortable in mostly female environments (this probably came from being thirteen and being constantly made fun of by the other boys in my class, as well as growing up with two older sisters). While I’d hesitate to call myself a feminist, mainly due to my concerns about being appropriative, I would say that I have an enduring interest in gender politics that I do my best to express through my actions.

This interest began to manifest after unrequited crush no. 4,523, around my mid-twenties (I’m in early thirties now) when I began to wonder whether the reason I was so unhappy about my lack of meaningful romantic relationships was because of my attitudes towards women. It has, I believe, helped a lot internally: by working to change a lot of my problematic behaviors and mindsets, I’m not nearly as hung up about sex and relationships as I used to be, and overall I do feel like I approach thoughts about women in a much more healthy way than I used to, helping me get out from being the seething ball of bitterness and anxiety that I was when I was younger.

Despite this, however, dating still fills me with dread, and even though I no longer look at my lack of a love life as some sort of scathing indictment of who I am as a human being, I’ll admit that I’m still kind of lonely and would like a relationship, or at the very least to get laid more than once or twice a year. However, I seem to not want to do anything about it because I can’t help but think that everything that could be done to do so upholds some unhealthy societal norm.

So, for example, when my friends comment that a cute woman has been flirting heavily with me all night, and tell me to go for it, I say that there’s no way to tell what she’s really thinking and that the last thing any woman needs is to feel like she can’t communicate the way she wants to without some entitled creep getting entirely the wrong idea, and that some people are just naturally flirty and we shouldn’t assume that that’s some sort of indicator for desire, and that if she REALLY liked me that way she would have made it much more clear, and I don’t want to assume that any display of friendliness is automatically some attempt to get something going, because that’s a real problem in the way men and women interact nowadays. And then I bring up that she has a boyfriend, and I should respect her choice and it’s creepy to hit on someone in a relationship as if I know more about what she wants than she does. And my friends go, maybe she wants a new guy, to which I say, “If that were the case then she can say it and make things clear and unambiguous because I’m not going to try and override a decision she made about her own life.” This, incidentally, is the point where one of my friends says, “You’re letting your feminism get in the way of your game,” which makes me think but, at the same time, I think it would be safer to err on the side of not doing anything to avoid contributing to a toxic environment.

Or, talking to my one sister about a very attractive woman at one of my group activities, she said why not ask her out, and I said that she probably didn’t join the group to meet guys and I shouldn’t create an atmosphere where she has to worry about being hit on constantly. Besides, I just *know* she doesn’t think of me that way (I mean I don’t really know for certain, but I generally make the assumption that women aren’t interested in me that way, so why bother with someone I think isn’t interested?). So I don’t want to make her uncomfortable or anything. Or when my sister’s husband asked whether I ever talk to attractive people I see on the subway, and I respond that that’s the LAST place anyone wants to talk to a stranger and that women are harassed all the time by people who can’t take a hint and I don’t want to be one of them because nine times out of ten everyone on a subway, men and women, just want to be left the fuck alone.

Or, last week, I was hanging out with two friends of mine, both female, and one of them began giving me some sort of vibe that involved sitting MUCH closer than necessary, initiating much more physical contact than she had ever before, and also briefly and purposefully stroking my fingers under the blanket. When the other friend left for a bit to walk her dogs, she looked up at me and said she couldn’t concentrate on the movie, and I kind of just froze and said that I thought we should watch (stupid, stupid, stupid) and she harumphed and moved across the couch and bundled up her blanket and crossed her arms and acted weird to me the rest of the night. But I’ve known her for two years and she never had given me any indication that she was interested in the past, and neither of us were at all sober and I don’t want to be predatory and take advantage of someone, and she shouldn’t have to be concerned that I would try, she should be able to have fun and get fucked up with guy without having to worry that he’ll try to fuck her. And how do I know that what I perceived as flirty behavior isn’t just all in my head and she didn’t mean anything by it? Because that happens, not just to me but to people everywhere. But her reaction made me think I fucked up somehow, and I ALSO don’t want her to think I was necessarily rejecting her because she’s WAY cute and awesome and smart and principled and if I’d known I was good to go I totally would have gone for it, but I felt the situation was too ambiguous and now I’m worried I made her feel unattractive in that moment, which I know from experience is a terrible thing to feel.

So, things like that. Not helping matters is that the times when I have thought I was good to go, it turns out I had miscalculated, which made me feel awkward and probably made her feel that way too, and so I’m just crappy at trusting my instincts when they’re telling me “say you want to kiss her!” because I’ve been wrong so often in the past and it’s felt terrible and I don’t want to feel that way.

And so I’m wondering whether all those fancy explanations that I wrap up with deep political meaning are just excuses to justify me not pursuing the relationships I want, like the problems I’ve always had with sex and dating just went to grad school and came back with an MA in women’s studies and philosophy but, at heart, is still the exact same problem. It’s the same fear — that there’s something fundamentally unlovable about me and if I ever express a desire for someone in any way, they won’t like me anymore because how could I even SUGGEST such a thing — except dressed in big words and given some sort of political justification. Like, it’s not that I’m shy and need to learn to take some risks, it’s that I’m not going to impose myself on someone who just wants to be left alone and live her life and have male friends who don’t try to hit on her, because I refuse to be That Guy. They’re different mindsets, but it’s the same result: I don’t bring up the topic of possibly dating people I’m attracted to and decide it’s not that bad having a new friend, because, obviously, awesome people don’t stop being awesome just because they’re not sleeping with me, and I want to have awesome people in my life.

One thing I’ve been thinking about is that my mindset could be making this assumption of sexlessness on the part of women, as if they don’t also have bodies that get horny as well, but I’m not sure if that’s really reflective of my thoughts because I acknowledge that women also want to have sex, I just have a very difficult time thinking they want sex with me. And then I’ve been thinking that it’s unfair to expect women to take on all of the risk in romantic interaction by wanting them to make the first move and not responding to anything unless they make their desire abundantly clear, because as a man who was raised with the expectation that I’m the one supposed to do all the asking, that fucking sucks and why do I want to burden women with having to do that. But, on the other hand, it sounds like WAY too convenient an excuse and could just be my mind trying to rationalize the predatory hunter/prey model that has caused so many problems in the first place! We must always police ourselves for bad thoughts, I believe, for the oppressor within can be far more tenacious than the oppressor without, and I wonder whether this is just the inner enemy speaking.

So you can see I’ve been having a rough time and possibly missing opportunities to find what I want in other people. It’s only recently, though, that I’ve started wondering whether I’m hurting other people by doing this, people who may have actually wanted me but I refused to respond because I didn’t think things were clear enough and I didn’t want to risk making them feel shitty, which in turn could be making them feel shitty (admittedly, it’s the final example that got me wondering this).

Am I overthinking all this? How do you both pursue the relationships you want while still staying true to ideals of gender equality? How can you be more comfortable expressing what you want while not going overboard and becoming an entitled creep? And, finally, should I have kissed that girl in the last example?

Sincerely,

Just a Dude

Dear Just a Dude,

Dude. There’s this movie, “Legends of the Fall,” that’s ostensibly about three brothers, all in love with the same woman (Julia Ormond). But really, the movie is a soft porn bodice-ripper for ladies who saw Brad Pitt in that one small role in “Thelma and Louise” and decided that he was tasty man candy. If that sounds hard to believe, go watch “Thelma and Louise” (Again. You’re a male feminist, so I know you’ve fucking seen it.) and you’ll understand why Pitt had a certain undiscovered-fuck-toy appeal back then. He had this weird country-cousin allure that made him exactly the sort of squeaky plaything you wanted to ferret away to a secret corner of the house and chew to tiny little bits.

I saw “Legends of the Fall” in a crowded theater on opening night because my Irish boyfriend loved to see cheesy American blockbusters on opening night in America, among Americans. We both knew the movie would probably be stupid, and it WAS stupid, but that incited more rowdy audience back-talking, which was the real point.

Anyway, there was this one scene where scruffy cowboy Brad Pitt asks his little brother, Elliott from “E.T.,” (Henry Thomas!) whether or not he’s fucked his brand new, smoking-hot fiancee, Julia Ormond. Elliott says something like, “I am not… That is not… When the time comes, after we are legally married, we will… m-m-make love.”

Brad Pitt replies, in a low growl, “I suggest you fuck her.”

So that’s pretty much the sum total of my advice to you. I suggest you fuck her.

The fact that you go from NOT wanting to hit on women with boyfriends and NOT wanting to hit on women on the subway (both reasonable) straight to NOT wanting to respond in any way to an obvious expression of sexual interest (by a woman who interests you!) really underscores how much you’ve overgeneralized this problem, confusing reasonable self-restraint with some overall philosophy of non-intervention.

Stop analyzing the psychosocial and political layers of every single interaction with every woman. Are you interested or not? If you are, say so. When a lady is fondling you on the couch, that typically indicates that she’s interested. If you’d rather say, “Can we pick this up when we’re not drunk?” that’s great. If you want to say, “Can I kiss you?” that’s also good. But freezing up and getting confused and then feeling bewildered by her silence and anger, but not saying a word about any of it, and THEN slicing and dicing the whole thing intellectually, passing it through every high-minded filter known to humankind? This is a squandering of precious youth, an offense against hormones and nature and humanity. PLUS, WHO HAS THE ENERGY FOR THIS SHIT? Open your mouth and speak. Say what you want. Politely stating your desires in the presence of an apparently interested human being is not a high crime against womankind. It just isn’t.

If the woman in question isn’t interested, she is free to tell you that. What’s the problem? Where is the insult or injury there? Give a woman ample opportunity to set you straight. Feel free to apologize for presuming. But don’t apologize for even CONSIDERING opening your mouth. Admitting that you have attractions and desires does not make you an oppressor. No.

I can see why your friends are encouraging you in such a wide range of situations, some of them not entirely comfortable. They just want you to stop thinking so much and do something, ANYTHING. Because you are not some stalking carnivore that needs to be shot. Stop worrying that it’s offensive or poisonous or wrong to think or say this or that. Yes, I do admire your EFFORTS to always police yourself for bad thoughts. I agree that people should try to honor their highest selves, rather than merely assuming that their behavior will naturally match some stanky half-assed selfishness displayed by the lowest common denominator of humankind. But I think that these valiant efforts of yours, and all the analysis you put into every single wasted moment of your squandered existence as a virile young human being, are clearly beginning to stand in the way of your happiness. Instead of thinking quite so much about every dimension of what a woman wants and thinks and feels, I would suggest spending a little time getting to know a woman, or a few women, who interest you. That means asserting yourself. Speaking up. Saying what you want. Telling someone how you feel.

After you start dating someone? Trust me, THERE IS PLENTY OF TIME TO SLICE AND DICE EVERYTHING YOU DO IN A RELATIONSHIP. You will have many, many opportunities to recalibrate and reconnoiter in order to ensure a totally egalitarian pairing. The entire power dynamic of a union is not established and then set in stone within the first few milliseconds of a given interaction. There are multiple times, over the course of a relationship, to reconsider your actions, give more generously, reassert your interest in your partner’s feelings, inquire after your partner’s comfort. All of these things are likely to go well for you, because you care. Healthy women will appreciate your ability to put them front and center, to listen, to sensitively take their feelings into account at every turn.

But in the beginning, it’s pretty black and white. There is desire, or interest, or a spark, or there’s nothing. How will you know if you don’t ask?

Do you need to analyze whether or not you seem predatory, or wonder if you’re creating the wrong atmosphere? I’m not saying there aren’t situations where these questions might be appropriate and even welcomed. On the subway, or in the company of a woman with a boyfriend: Good idea. But I’m just going to go out on a limb and guess, based in part on what everyone else is telling you, both with words and without words, that you are not in clear danger of behaving predatorily in an everyday situation with a woman who’s FONDLING YOU UNDER A BLANKET.

You are, however, in danger of hiding in your hidey hole forever, of ignoring bright, flashing “COME CLOSER!” signs, and of never ever kissing a pretty woman or dating a lady or doing anything, at all, ever. You are in danger of remaining paralyzed by your neurotic thoughts indefinitely.

And that’s a cop out. Your overactive, pro-feminist, hypercritical imagination is a cop out. You are more comfortable writing endless, winding sentences about why you shouldn’t act, why it wouldn’t be RIGHT or GOOD to act, why it’s NOBLE and DECENT and RIGHTEOUS not to act, than you are with action, and desire, and the feeling of feelings.

I have to admit, there are a few red flags in your letter. First, you describe your past in very vague terms. What are you talking about? It’s tough to tell. Second, the women in your letter are suspiciously faceless and interchangeable. You didn’t offer a concrete detail about any of them. You seem to find them appealing, but it’s never clear WHAT EXACTLY you like about any one of them. Does one woman excite you more than the others? When a faceless multitude of women add up to a problem? That’s a little suspect. Let’s not just skin the damn cat, here. Let’s unearth your true desires and feelings and figure out WHO out there is lively and spontaneous enough to blast through your complexly constructed web of rationalizations and teach you to live a little, goddamn it.

I’m not sure you know what you want, though, because you’re blocking your feelings with this rambling, self-blaming paralysis of yours. You need to make less room for your thoughts, and make much more room for your feelings. I suggest you stop thinking, listen more, ask questions, and feel your feelings. I suggest you smile at the woman you really do like. Notice how that feels — making eye contact without apology. I suggest you ask if you can kiss her. If these things go well, I suggest you talk about your attraction to each other. I suggest you express your interest without qualifying it with disclaimers and intentions to ensure that you are not in the least bit offensive or suspect. I suggest you leave all of the complicated sociopolitical ramifications out of this picture at first, if at all possible. And if all goes well? I suggest you fuck her.

Because you are not a walking encyclopedia without a working penis, are you? You are not a sex offender, either. You are not poisonous, simply because you’re a man. You are a polite person. You will ask her for her consent many times. This is clear. You will be kind and you will pay attention.

But you’re not a fucking computer. You ARE an animal. She is an animal. This is a good thing. I suggest you fuck her. And if you’re lucky, she’ll recognize that she’s an animal, and she won’t get clouded up by her self-consciousness and self doubts and she’ll fuck you, too.

Now obviously, there are people who will read those words and assume that I mean, “DOMINATE THE LADIES, MALE OPPRESSOR!” Get real. I’m not telling anyone to become a player overnight or fuck and run or hit on women with reckless abandon. We all know about rape culture and the insane rape-y shit happening all over the place. Go read that long New York Times article about the woman who was raped at Hobart and William Smith Colleges. I mean, seriously, WHAT THE FUCK IS HAPPENING OUT THERE?

But let’s not let our criminal caveman culture keep us from realizing the full force of our sexual potential. Early feminists, suffragettes, and enlightened men have fought very hard to assert that women are not merely vessels that make babies or vessels to get fucked, we are sexual beings with thoughts and desires of our own. Please don’t infantilize us with your condescending, overconcerned intellectualizing. I know you mean well. You want a new, more helpful narrative? We women want what we want, just like you do.

You’re not evil. We’re not helpless. Get over yourself. Put your ego aside. Far less is at stake in a single interaction than you believe. The hero doesn’t succeed or fail here. People out there find love when they learn to show up and be themselves. I know, you’re shy. That’s why you have to practice a little, and make a few mistakes. Stop trying to protect yourself. Stop trying to control the outcome. Stop trying to remain perfect and harmless and blameless. Turn off that twisted brain of yours for once and just say what you want and ask what she wants.

You have the rest of your life to bring gender equality into your relationships — at home, at work, everywhere. You will always do that, and god bless you for it. But there is a limited window for saying, “I want to kiss you. Can I?”

Don’t think. Feel. Ask. And if the answer is yes? Go for it.

Polly

Do you wish Brad Pitt would say something to you in a low growl? Write to Polly and discuss!

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses.