Get Ask Polly delivered weekly.
I’m a middle-aged man who should be enjoying life, but instead I’m unable to avoid wallowing in my (not really that awful) past.
In high school and college, I was the archetypal nerd. Before this was cool. I was fat, I had few friends, I had obsessive interests that no one shared. And girlfriends? Ha!
After college, I ended up in a dull and unsatisfying job, and managed to meet someone who tolerated me enough to marry me. The fact that she treated me with cruelty was something that I didn’t notice for years, I was so happy that anyone would have me.
Eventually, with the help of a great therapist, I dug myself out of all these holes. I learned how to communicate better, got really fit, learned how to dress well. I got a true career that was enjoyable, well-paid, and brought me respect. I was able to realize my wife’s behavior and got divorced.
Right now, everything should be fantastic. I’m 43, successful, and fit. I have no trouble meeting women, and they clearly want to be with me.
But I’m not enjoying it at all. Sure, there’s the moment when I meet someone new, and feel great that she actually wants to sleep with me — who’da thunk it? And it’s nice to go to cocktail parties and see people be impressed with what they think are my accomplishments.
But in the end, I feel like a fraud. Every time, I think that people will quickly realize that I’m still a fat, boring nerd, and then think even less of me for pretending I’m not. This is true no matter how they react — if women think I’m amazing, I think they must be idiots not to see the truth. If they think I’m a flawed human who’s done well, I focus on the flaws. My ex-wife, who still badgers me for money, resents everything about my current life and constantly reminds me that I’m really a worthless jerk inside, and I’m unable to dismiss her because I think she’s right.
My therapist is no longer helpful; she thinks that I’ve come so far and should finally be happy with life.
Polly, I know that lots of people had it worse. It’s not like my parents beat me or I grew up alone. But I can’t help returning to my lonely high-school days and feeling like that’s who I’m meant to be. I’ve worked so hard to get out of that; what can I do to truly accept the new me?
Thank you for your help.
Dear Fat Nerd,
Little-known fact: Nothing in the world is less interesting than men who have it all and have always had it all. As tempting as the heteronormative fantasy of a confident, charming, handsome, masculine man who never doubts himself might be, not only are there very few men like this on the planet (because we ALL doubt ourselves!), and not only are there very few smart men who fit into this category (because smart people have big, neurotic brains that are usually custom-designed to eat themselves alive), but very few smart, thoughtful women will feel supported and satisfied in an intimate relationship with such a man. Because as hard as it is to navigate the world for ANY PERSON, it’s even harder for a woman. Being a woman is really fucking hard. Even if every single human being in your life is 100 percent egalitarian and you go to the most progressive school on the planet where you’re surrounded by nothing but wonderful, caring, sensitive human beings, eventually you’re going to turn on the TV and realize that our culture mostly sees women as either lumpy comfort machines or fuck dolls. And then you go on the internet and discover that if you have the fucking audacity to define yourself as a human being, you will be subtly (and not so subtly!) chided for it. Present your own unique thoughts and opinions as a woman, and watch how quickly a gaggle of threatened idiots scrambles to make you feel like either a used-up, lumpy old broad or a fuck doll. Asserting your right to be a regular human being is not only chafing to these people, it’s an insult to their sense of themselves as the rightful owners and definers of everything.
And even though, generally speaking, most of these hyenas are deeply insecure animals who were told that they would rule the universe, only to grow up and discover that some of the subhuman half-persons around them have other ideas about who should and shouldn’t rule, they have adopted the same strut and swagger and sense of entitlement of their rarer and less insecure brothers. They fear weakness — in themselves and others — because they’ve spent their lives aping the heteronormative fantasy of a confident, charming, handsome, masculine master of the universe. So, for our purposes, the deeply insecure, narcissist fakers of confidence and that very rare species of deeply confident, unquestioning macho dude are one and the same. The insecure ones are usually smarter than the simple, non-self-doubting cowboy types, but their outward behavior is the same: They don’t understand women and they fear women, and they deal with this by silencing women and butting in when women are talking, and by persistently and tirelessly working to make women feel embarrassed about themselves. They do this with strangers on the internet, and they also do it with female friends and female co-workers and lovers and wives. When they’re dating, they view women as their own personal, cheap, constantly replenished all-you-can-eat fuck buffet.
Now let’s talk about you. You have doubted yourself from childhood. As a result, you understand what it feels like to question yourself, to feel alienated, to feel weak. You understand what it means to struggle to hold back your real emotions. You understand what it means to feel like an imposter in everything you do. You understand what it means to try very fucking hard to mold yourself into a shape that the world might like, and you know what it’s like to succeed at that and still feel like maybe people only like the part of you that you beat into submission. You know what it’s like to suspect that all anyone really wants is the SHELL of you, how you will SEEM to others, how you will fit neatly into a slot, hopefully without making too much noise or letting everything wild and beautiful that’s deep inside of you leak out.
I’m not suggesting that only those with a past as a so-called fat nerd can see straight into the souls of women (or even that every woman alive recognizes these energies and dynamics at play in her own life). All kinds of men have been through all kinds of shit, and even plenty of those who haven’t been through anything more challenging than a delayed growth spurt while they were sophomores at Choate or that night they wrecked their BMW on an icy road in Connecticut STILL happen to be open-minded and self-questioning and sensitive. If you’re smart as hell and you resisted the mainstream views of what a man should be, chances are, you have what it takes to try on for size the experience of growing up in a world that views you as a subhuman sex toy that will one day age into a comforting piece of overstuffed furniture.
You’re going through something right now that thinking women go through THEIR ENTIRE LIVES, starting sometime in middle school. “I thought this guy loved me, but when I say something true and real for me, he cringes like I’m dipped in shit.” “When I cry, he says, ‘Good thing you’ve got such a nice ass, or I’d never put up with this crap.’” I can’t tell you how many times I asked myself, at the end of a relationship, “Did he like ME, or my ass? Did he like me because of my personality, or in spite of it?” Half of my boyfriends dated me because I was an obvious catch and dumped me because I was a regular mortal human being with feelings who wanted to talk a lot and feel a lot. I was repeatedly made to feel like a crazy person for having feelings at all.
What’s interesting is that you now run the risk of following the trajectory of a deeply insecure 23-year-old woman, questioning yourself so repeatedly and relentlessly that you develop an eating disorder or you start self-harming. Or you could end up dating a woman who loves handsome, successful men but doesn’t really want to hear about the chubby kid who lives deep down inside of you.
Listen to me: I love your chubby kid way more than your fit, professional exterior. And I know that there are many, many women who will feel the same way.
My husband was a real nerd when he was a kid, too. He had no confidence, and on top of that, he was raised in a big Catholic household in the ‘60s, which is a little bit like being raised in a barnyard. As long as everyone is eating and no one is bleeding out, the whole operation is considered a success. He loved his mother a lot, but she said very beleaguered ‘60s-mom things, like, “No one wants to hear about your problems, so keep them to yourself.”
By the time I met him, he was handsome and successful, but deep inside, he still felt like a highly rejectable nerd. That summer, he’d been dating a lot of women who very much wanted to be with him. But he often got the feeling that a lot of women saw him as a catch who would “fix” their lives and sew everything up just so. They seemed fixated on sealing the deal before they even know who the hell he was. He suspected that the second they knew that a self-doubting nerd was lurking inside him, they wouldn’t love him anymore. OR — worse yet — they’d pretend that they were fine with it, and he’d settle down with one of them, only to discover that she was actually pretty repelled by him as a human being.
Of course, when I met him, I immediately started digging to find something interesting — a former chubby kid? A neurotic who doesn’t know how to just be? A twitchy, self-loathing nerd? At first, though, he painted this picture of himself as a busy professional who mostly liked to drink and surf. And I’m not gonna lie, that was kind of hot. But I was worried. Because as long as he was JUST a handsome and successful and confident adult with no ugly underbelly, I knew he’d never stay interested in me. I was too fucking messy for some busy professional guy. And I didn’t want to be busy, busy, busy all the time, the way a busy, ambitious professional likes to be. I didn’t want to drive across town to surf and go out to parties and act fabulous. I wanted to lie around in bed together, eating aged cheeses and watching Deadwood.
So I dug, and eventually, I found the so-called unlovable nerd inside of him. And at first it was jarring, because I was used to being with guys who would never in a million years admit their insecurities. It was also jarring to be with someone who really saw me and loved what he saw. His gaze made me uncomfortable. This guy must not be as good as me if he likes me this much, some pathetic, insecure part of my brain told me. I was embarrassed at what a terrible person I was, that this amazing guy loved me, and even though the sex was great and our times together were perfect and I loved his sensitivity and openness and even his self-doubt, it didn’t feel like home. Home was a place where people tried to act cooler and less caring than they actually were. Home was a place where people ignored each other and turned on each other and suffered in silence.
Jesus, that’s sad. And I almost pushed him away! But some voice inside my head said, Christ, woman, if you kick THIS guy to the curb, then you really are beyond hope.
I’m telling you all this because I don’t want to pretend that it’s easy. You’re facing a complicated psychological thriller no matter what. That’s just how it feels to be smart and complicated, and to try to make a life with another smart, complicated human being. That’s just how it feels for someone who is afraid that, deep down inside, they’re unlovable.
But you need to understand this: MOST PEOPLE ARE AFRAID THAT THEY’RE UNLOVABLE, DEEP DOWN INSIDE. The only difference between you and them is that you think it defines you, that you’re EVEN MORE FUCKED than them, that this self-doubt will crush you completely, in time.
I often suspect that I am uniquely fucked, too, even now. I still have to remind myself that these things are normal. I have so much evidence in my inbox that they’re normal, but I still have to remind myself, over and over and over! And so do you.
Your therapist is tired of hearing this. This only means that you need a new therapist. (Stop talking to your ex-wife, while you’re at it.) This also means that you need to find a partner who’s curious and engaged, and who isn’t constantly distracted by her own rigid notions of what a man should be. This woman won’t be THAT easy to find, and even once you find her, she might get confused by your insecurities. In fact, if she’s a good match for you, her insecurities will dictate that YOUR insecurities freak her out a little bit. Tolerate that. And tell her this: “You are afraid of this because you see yourself in me.” And when you meet a woman who’s insecure, and it freaks you out a little that she’s insecure (sounds impossible, I know, but just you wait!), remind yourself: You are afraid of this because you see yourself in her.
The remedy is to love your insecurities the MOST. Love that chubby kid so fucking hard that he’s all, “Aww jeez, I get it, you adore me! Enough already!” Look at old photos of your supposedly awful self as a kid and love that sweet, confused kid with all of your heart. This is the best part of you, not the worst part. This is the real heartthrob, not that handsome, fit breadwinner exterior. Plenty of women will agree with me on that. PLENTY OF WOMEN. Trust.
Because you know what the alternative to men who doubt themselves and admit it is? Unquestioning insecure masters of the universe: They hate their own humanity, and yours! Go look at a photo of Martin Shkreli if you want to know what that looks like to women who have their eyes open and can fucking see. That’s the face of someone who’s incredibly entitled and incredibly insecure and, most of all, incredibly determined to seem infallible NO MATTER WHAT, and that’s why it’s hideous and also why we can’t look away.
So don’t fear your insecurities. When you hate yourself for your own weaknesses, you bend the arc of the universe toward Martin Shkreli. When you hate your own fallibility, you embrace the ethos of threatened, enraged harassers and insecure, narcissist fakers and snarling hyenas. When you insist that your low self-esteem makes you unlovable, you’re doomed to a life of pretending, a life of wearing the proper mask just to stand in line at the dehumanizing all-you-can-eat fuck buffet. Don’t dehumanize yourself and your sexuality. Refuse to reduce yourself to your assets, and don’t reduce women to their assets either.
Don’t figure out how to accept the “new” you. Figure out how to accept the old you, because he’s not going away. He knows that HE lies at the center of everything that’s good about you. He knows that he holds the key to a new life for you, a life that’s not about shedding some important part of yourself so you’ll be accepted by the faux-confident, skin-deep masses. He knows that you have to walk this whole slick-guy thing back, waaay back, and own and embrace that chubby kid for the first time. The chubby kid wants to come out of hiding. He wants your love. He wants to be invited to the party.
It will be a much better party with him there, trust me on that. The chubby kid loves a good party, and he knows how to love, he knows how to feel, he knows what you really value, what really makes your heart soar, what feeds you. He knows how to keep you alive. Let him show you what he knows. Let him in.
Get Ask Polly delivered weekly.
All letters to email@example.com become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.