Ask Polly: I'm 40 And No Man Would Want Me Now!


Hi Polly,

So, I was dating someone long distance (YES I KNOW). Though I thought it was going well, he ended it — and now I’m not sure if it’s good for me to be friends with him (YES I KNOW JUST HOLD ON).

I’m a 40-year-old gay guy who’s never dated anyone longer than 9 months. This year I finally felt ready to settle down (not immediately! this takes work!), though I know that may not be possible at this point. I’m smart and ambitious, but with some major problems I’m finally working on (sorting out issues from my college-era drug use, always had difficulty maintaining friendships). Though I’ve always made life choices based on career opportunity, they haven’t always panned out, and there have been a couple spans of lean years. (For context, the men in my family follow this same life arc: troubled youth, then settling down. Maybe some behavioral genetics are playing out here.)

If you’re not married by 40, there are usually a few possible things Wrong With You: you’re unattractive (nope, healthy self-image), you’re crazy (under control I guess?), or you bail on good things. I used to run from relationships; now I’m patient and let them play out. But I have insanely high standards, so good things rarely come along.

When I was a little boy I was really lonely: one older brother who bullied me, and the only other kid in the gifted program who moved away, leaving me to become poorly socialized with boys I saw as below me. I was subtly encouraged to avoid friendships with girls, though I found those in college. But I never recovered from losing the one guy like me, and as an adult I’ve been an isolator.

So I’ve always felt like I lacked my guy-geek best friend, my Lego co-builder, my brother-in-code. I have a family-shaped hole in my heart, but kids are basically off the table now (no nieces/nephews either), and all I want to do as the clock ticks on down is keep the old friends I have somehow held onto, and keep the new people in my life who make it worth living.

You’re supposed to be happy with someone who’s, say, 75% of what you want, right? This guy was 90% (except for living a short, cheap flight away). He’s handsome, my physical type, with a lush and gorgeous beard, age-appropriate, a complete match in the bedroom, sweet and sensitive, grew up in a similar kind of dysfunctional family, never judged my problems, only supported them, and, maybe most important, a socially-competent math whiz (BONERBONERBONER). We programmed together, cooked amazing meals, traveled to places whimsical and mystical. It felt like I was finally building something. I can honestly say that though I’ve dated and fucked a zillion guys by now, I’ve never met anyone like him. I thought he felt the same way; after getting to know each other a little, he declared, over one of those romantic dinners I never seem to get: “You’re so much of what I want.”

But after a few months of weekend visits, and a span of a few weeks on vacation, it turns out a relationship wasn’t what he wanted — but no word on what he did want. As you said, Polly, sometimes guys sense any change in cabin pressure and they just run for the hills, and we never get to know why, there is no why, he just runs from good things and that’s not your fault, stop torturing yourself already!

I stopped trying to figure out why, and have just been letting the reality wash over me, accepting it, trying to feel the shape of what my heart looks like now. He’s getting tenure in his city where Nobody Walks, and I’m in love with my city where Everybody Bikes. I was open to the idea of dating for a year first, but if anything had gotten serious, I’d have had a hard time leaving, even though the dating pool is small and most hookup opportunities are with already-taken guys in open relationships (ugh).

But he keeps texting to say hi. I know he’s never met anyone like me before either, but I’ve given up on the idea of us turning it around. Now I can’t tell if maintaining contact is going to turn him into the lifelong buddy I’ve always craved, or whether it’s picking at a wound I need to just let heal.

And with my history, tendencies, and standards, am I even likely to find anyone, or do I just get the cats and the garden, dress up as Santa for the local orphanage every year, and start work on the conversation-bot that will keep me from feeling lonely when I’m senile and need to pretend someone is still texting me? I mean, all that *does* sound like it’d make me happier than I am now.


Old Man-Maid

Dear OMM,

So there you were, swept away by this 90%, almost-true love, when your man disappeared. Should you stay friends and risk great pain? Or would you rather ignore his texts and allow him to take on the mythical status of The Gifted Boy Who Moved Away, serving as both lost love and lost Lego co-builder, symbolizing your one shot at happiness on every front?

At least you have a romantic vision of the future to guide you: “All I want to do as the clock ticks on down is keep the old friends I have somehow held onto, and keep the new people in my life who make it worth living.” Whoa, now! You’re flying pretty close to the sun, there, captain!

Of course, there’s always plan B: Cats, garden, Santa Claus, conversation ‘bot. But will they even let you adopt a cat, what with your “history, tendencies and standards”? You do know that playing Santa Claus at the orphanage is a pretty coveted role, right? Plus, if you create this conversation ‘bot in your image, making it just as cautious and self-protective as you are, unwilling to speak to anyone who is less than 90% right for it, who says it will even deign to speak to the likes of you?

Do you know why cats and gardens and Santa Claus outfits sound kind of good to you? Because those are the sorts of flawed, messy compromises that your life lacks right now. When you imagine giving up on your story completely (“the boy who got away and never came back, no one is good enough, I’m not good enough”) and you strip out the efforts to “keep people in your life” (which sounds arbitrary and sterile for a reason: because you’re not good enough and they’re not good enough), then you have to stuff something else into the empty space. Then you’re free from your own absurdly high standards.

So let’s try to disable your onboard superiority complex, with its unmatched level of statistical accuracy that keeps you safe from all human foibles. Let’s power down your motherboard once and for all. (I can just hear you now: “Technically you don’t ‘power down’ a motherboard, Polly, but I think I see your point.”)

Because once we cut off this very logical, alienating processor of yours, that’s when you’re free to start living in an entirely new way, whether that means adopting cats or growing a garden that you struggle to keep alive or building a conversation ‘bot, simply because YOU want to. And you might even give time to some orphans, with whom you secretly identify.

This circles back to my comments last week about creating a beautiful vision of your future as a single person, so that you know you’ll have a great life with or without your imaginary dream mate. It also circles back to times I’ve urged letter writers to lean into their vulnerability (a few people have asked me what the fuck that means, in fact).

The beautiful vision and the vulnerability go hand in hand.

Your first challenge is that you lack a compelling vision of your future. You would never dare to dream of something so grand as meeting the most amazing man ever, falling in love, and having kids. Your history, tendencies and standards, added into your chronological age, render this pursuit statistically impossible. According to you, you will be lucky to meet a guy in an open relationship, or a guy who’s great but isn’t looking for the Lego co-builder of his dreams. You will be lucky just to hold onto the friends you haven’t alienated yet. You will be lucky to bide your time as the clock ticks on down.

WRONG. You need a beautiful vision. Go buy a really nice journal and write down exactly what you want from the next 10 years of your life. Go nuts. Approach this work with a spirit of optimism and gratitude. If that requires a little extra coffee, so be it. Go to some mountain top in Bicycle Town with a triple latte and write write write. Be romantic. Get wild. Fly close to the sun for once, goddamn it!

But before you set pen to paper, hear me: YOU are the gifted boy who moved away. You have been here the whole time, waiting for kindness, waiting to stop being bullied or ignored. It’s time to stop bullying yourself, to stop telling stories about family-shaped holes. You are not damaged beyond repair, your history and tendencies and standards are not deal-breakers. It’s time to give yourself the right to want a lot. You deserve a lot. You are good enough right now, to have everything you’ve always secretly wanted.

So that’s the first part: Sketching out your beautiful vision of your life, alone or with another person. It’s a fantastical portrait of what you could be, if you applied yourself a little. For example: “I have a gorgeous mansion by the sea, just like Gatsby except I genuinely love all of my beautiful shirts, and I would never throw them all over the place, because they really do complete me!

There’s a kind of overachiever’s ball in play here. But it’s also about counteracting your compulsion to lower your expectations because you’re not good enough and don’t really deserve much. Behind every superiority complex, there’s an intensely insecure person who just wants to be loved, truly madly deeply loved. 40 is not that old. Why not dare to dream?

The second part of your vision — and maybe the most important part, for you — is about cultivating your own vulnerability and openness. That’s the Santa-at-the-orphanage, cats & garden part. Because what lots of overachievers don’t realize is that understanding your life in the absence of success is just as important as understanding your goals.

Some people settle for too little, strangely enough, because they’re afraid to be vulnerable. We women are much more likely to say “Hmm, this dumpy asshole will do, because he really seems like the kind of dumpy asshole who’ll never leave me for his secretary.” We don’t even know we’re compromising, because the message that we should always be humble and grateful is flashing in our faces. Our culture asks: WHO DO YOU THINK YOU ARE, BAR REFAELI? BROOKLYN FUCKING DECKER?

(The irony, of course, is that the dumpy asshole is even MORE likely to dump you for his secretary than the other guy, because you two aren’t a good match in the first place.)

The bottom line: Stop playing it safe. That doesn’t work. You’re not engaged with the world around you, and the scary thing is that you actually believe that that’s YOUR DESTINY. Because you’re Not Good Enough.

If I were you, I would call this bearded mathematician and tell him you are in love with him and you want the two of you to be together, somehow, some way. He will say “No.” FANTASTIC! Now you know he’s just texting you because he likes fucking you and wants to try to hit it the next time he’s in town. It’s time to come on that Hampton blouse, and move on. Don’t befriend him, don’t fuck him, and don’t keep him in the nowhere zone of BIG IMPORTANT SYMBOL, like the mythical Boy Who Moved Away. Move. On.

There’s also danger in treating yourself like a mythical symbol of something better than who you actually are. I’m not trying to be mean. I feel thankful for how vividly you’ve painted your portrait here. I mean this is a first act that practically writes itself. And in the romantic comedy of your life, this would be the point where THE HERO HEARS THE CALL. You’d probably be chugging along, As Good As It Gets-style, all controlling and lonely, and some sloppy loud-ass mess of a man, a mere 20% of what you want, would bust into the picture and kiss you passionately then wipe his big dirty body on all your linens and make you claustrophobic, and you’d kick him out and roll your eyes and then you’d pull your china doll down from a high shelf and cry and cry and cry and smash it against the wall and then weep and snot and moan and… This isn’t a very good movie, is it?

But then the sloppy guy would come back. He’d say something like “I love your uptight, not-good-enough ways. And I love your history, tendencies and standards.”

OK, hold on. That’s not quite right. That won’t happen, because no one loves history, tendencies and standards. You know what they love? They love naughty cats and untamed not very perfect gardens, and Santa Claus outfits that hang lovingly in the hall closet all year instead of getting packed away in moth balls, which would be more sensible. Sloppy, lovable, passionate guys love lonely men with half-built conversation ‘bots that will barely speak to them. They love Old Man-Maids with friends who aren’t just being kept around as the clock ticks on down, but friends with names and their own problems, who are being heard and appreciated and showered with dorky little Old Man-Maid gestures — slightly wilty flowers from the garden, baked bread that maybe isn’t as good as the last batch.

So, after you sketch out your beautiful, fantastical vision of the future, I want you to write down what will happen if you fail, here and there. What will you do instead? How will you manage to be happy anyway? What’s weird is, this vulnerable vision sometimes seems even better than the beautiful one, once you work on it for a while. Personally, I used to picture being alone and adopting lots of dogs and dressing like a serious freak. I don’t know why I found that comforting, but I did. You need to cultivate your crumpled, compromised vision of the future, too. At the center of that vision is you, our vulnerable, flawed hero. You know that everyone loves a vulnerable, flawed hero, right? This is why Seth Rogen has a career in the first place.

Vulnerability is your key to feeling your way to a brighter future. Calling the guy in the other city and telling him your feelings. Deigning to date random dudes who are maybe only 40% right and can’t balance their stupid checkbooks. Holding out for good chemistry, sure, but waiting and seeing if you might be attracted to someone unexpected. Making new friends simply because you’re curious about them. Daring to get hurt, and accepting the messiness of life.

Vulnerability means getting up in the morning and saying, “It’s ok to FEEL not good enough. But I am good enough.” Vulnerability means daring to contradict yourself, and daring to want some things that it’s illogical to want, like kids or ANOTHER beautiful bearded man who maybe isn’t exactly like you this time.

Children with superiority complexes want to find someone who matches them perfectly. “This mirror person who is just like me (and lovable) proves that I am lovable, too.”

Healthy adults can love someone who is different. You are already lovable, Old Man-Maid. You want to fall in love. Wear it on your sleeve. The people who own that desire are the ones who find love. You think it’s pathetic because you think that most things are pathetic. You are still pretty flippant and caustic.

So am I, by the way. But when I stick my neck out, good things come to me. The more I let other people be who they are, the happier I am.

How much fucking time do we have to feed our egos, as the clock ticks on down? Fuck ego. I like dogs and weirdos and funny women and smart men and also less funny women and less smart men. I don’t like people who want me to get the point really fast, or who think I’m wearing the wrong shoes. (I am.) There’s a kind of LA person who talks like he’s in the car, running late, and his head is on fire. I keep those people out of my life if possible.

Let’s close with a dumb story! Once this very successful acquaintance called me out of the blue, and he thought I was Heather Graham, because my name was right next to Heather Graham’s in his fucking cell phone. ROLLER GIRL AND ME, RIGHT THERE, TOGETHER! First he left me this ridiculous message, “Hey, we’re outside your apartment actually wondering if you’re around, we’re about to grab some drinks down the block.” I’m thinking: Whose apartment? Drinks where? Then he calls me a few days later, and he’s chatting in this spirited, trying-to-impress way (but his head is still on fire, of course) and finally he figures it out: I’m not Heather Graham.

So then he’s scraping for something to say, and all he comes up with is, “So, are you still doing the TV critic thing? Are you just going to… do that for a while?” AM I JUST GOING TO DO THAT FOR A WHILE. The implication being that I should be, I don’t know, strapping on roller skates and fucking Mark Wahlberg?

Are you just going to… do that for a while?

So after I put down the phone, I got a little wilty. “Being a TV critic IS pretty lame,” I thought. Shouldn’t I be doing something glamorous that this dude would respect? Shouldn’t I look much more like a fuck doll? Then I moved on to I’m Not Good Enough. WHO DO I THINK I AM, ANYWAY, HEATHER GRAHAM?

Finally I thought: That guy is a fucking tool.

The people who wonder if you’re wasting your time (the snobs, the pretty boys, the mega-uber hipsters) are usually wondering the same thing about themselves. What’s with this voice in your head, Old Man-Maid, who says your history will always trump who you are now, who says you’re too old to have kids, who says you’ll be senile soon and you’ll never find anyone who loves you for you?

All of the joy you’ve ever dreamed of feeling is within you already. The people who care about how much they matter are not the people who matter. The people who want things, who want beauty, who want to seem brilliant FIRST? The people who respond to you sticking your neck out by stepping on it? These are the bullies, or maybe they’re just distracted and they were really calling for someone else. Forgive them, but do not allow them to become symbols of anything.

You want love from that guy. You don’t really want friendship from him, and settling for friendship from him is really just a way of torturing yourself with his rejection of you. That probably feels natural to you. It’s time for longing to stop feeling so natural.

If you give your love, admit your flaws, open yourself up to whatever the world wants to give you, the world will open up to you. If you accept who you are right now and proclaim that this is a person who deserves love, who matters a lot, warts and worries and history and all? If you start to give yourself some of the things you really want, that are just for you? You will draw men with lush, thick beards straight to you. You will be become a Middle-Aged Man Magnet, not an Old Man-Maid.

Stop telling yourself stories about the things you can no longer expect and never deserved. Go fall in love and have babies and live your life. You are special, but you are no better than anyone else. You are just you, a gifted boy with a giant heart. Who do you think you are? It’s time to find out. This is only the beginning.


What do you think you deserve? Tell Polly!

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. Photo by “istolethetv.”