Ask Polly: I Am 40. Will I Be Alone Forever?

Appearing here Wednesdays, Turning The Screw provides existential crisis counseling for the faint of heart. “Because the heart is a lonely hoarder.”


There seems to be an abundance of advice-seekers who are 25 and terrified of being alone or 31 and think they’re elderly. What I don’t see is anyone over 40 who doesn’t have their shit together. Is it that they are too busy being surrounded by loved ones to read blogs? Or are they too downtrodden to bother?

There is a perception that young people are bundles of misguided anxiety and that time will sort everything out. And yet everything in my experience contradicts that. (It probably doesn’t help that I just finished reading The Lonely Passion of Judith Hearne. Why did no one stop me?!)

After a 13-year relationship, I find myself single — and 40. It’s not a divorce because I was never married. And marriage is not really the issue. Ninety percent of my friends are unmarried with no kids, and I’ve attended exactly two wedding in 20 years, both of them my sister’s (neither involved bridesmaids or a white dress). The issue is that I’m going on month four of what’s meant to be a year-long separation (no illusions there) and instead of having fun with my new freedom like I had envisioned (the separation was not my idea, but I wasn’t 100% opposed to it as a rut-breaking tactic), I’m miserable and panicky.

The problem is that what worked at 27 doesn’t at 40. Yet a good number of the women I know are still living as they always have. I don’t have good relationship role models. We like to stay out late, go drinking, be marginally irresponsible (which is all fine since we are wage-earning grown-ups) behavior that is all in line with the hipster punch line of a Brooklyn neighborhood that we live in. But a middle-aged version of “Girls” is not only horrifying, it’s not sustainable. I’m hyper-aware of the growing disconnect between my insides and my outsides and I feel queasy about turning into the oblivious old lady at the bar.

This seems to bother only me, though.

(The ex, who was age appropriate, also thought I was irrationally hung up on being older than everyone around me, but I don’t think men feel this as acutely. Case in point: I often see aging silver-haired dudes at shows, but never their female equivalents.) Nearly every female I know dates younger and for the time being it’s feasible since we could get away with shaving five years off our ages and no one would question it. But I don’t want to lie, plus I have a hard time with men who used Facebook as teenagers or were in grade school on 9/11. And the point is moot, because I’ve hit the invisible to the opposite sex point. At first I thought I was simply annoyed by youngsters dancing to Bell Biv Devoe because mindless nostalgia rubs me the wrong way (I learned to never trust a big butt and smile long ago). But then I wondered if I was more upset that youngsters who dance to Bell Biv Devoe have no interest in me.

I feel like all the grown-ups got married, never go outdoors after 9 p.m. and socialize by throwing dinner parties in their brownstones with reclaimed wood tables, small batch bourbon in Mason jars and kids playing in front of the chalkboard-painted fridge. Must I await the Dadurday of reckoning to score a viable divorcee?

The obvious solution is to try and meet people outside of bars — volunteering, church groups, poetry readings, whatever — or at the very least expand neighborhood boundaries. But even though I’m chatty (and long-winded, obviously), I’m extremely introverted and never start conversations with strangers first. Alcohol helps, hence the bars.

I’m starting to believe that at some point “there’s someone for everyone” is as untrue a platitude as “do what you love and the money will follow” or as annoying as people who claim to have lost 30 pounds once they stopped stressing over what they ate. I know I’m still new at this but I’m already feeling that I could just as well become a hermit in my new paycheck-eating apartment, ordering Thai food off Seamless and mourning the loss of Enlightened until I eventually keel over.

Are some people just meant to be alone? All my friends are, and now I am too.

Older, Not Wiser

Dear Older Not Wiser,

Back in the mid 90s in San Francisco, you’d see advertisements all over the place for Linda McCartney’s Meatless Frozen Entrees. The ads seemed to loosely refer to a food product of some kind, but all you knew for sure was that the “food” in question 1) lacked meat, 2) was frozen, and 3) was for some reason associated with the wife of the man who wrote “Hey Jude.” Say whatever you want about that lunatic Judith Hearne, but the woman did have passion. And if she put out a food product, you can be goddamn sure she’d tell you all about what was in it.

While I very much enjoyed your letter, it’s the 700-word equivalent of something meatless and frozen. Instead of telling me what you have and what you want, you describe what you don’t have and don’t want, while outlining what everyone else has and wants. The fact that you’re on a year-long hiatus from a 13-year relationship fits right in with the wishy-washy Nowhere Man feeling of your letter. You portray yourself as passively standing still against a background of action: Your partner suggests a break and you agree to it, vaguely hoping to break out of a rut. Your friends go out drinking and dating younger guys and you agree to it, vaguely hoping that it will stop feeling quite so wrong to you. You imagine married people sipping bourbon out of Mason jars at their dinner parties, but insist that marriage is not the issue. As bad as Judith Hearne might make you feel, she at least took action, installing herself in that inherited house in the country, then leering at the handsome young lad tending to the grounds. (Correction: I’ve confused Judith Hearne, the old-maid antiheroine of The Lonely Passion of Judith Hearne with Rachel Waring, the old-maid antiheroine of Wish Her Safe At Home. I strongly recommend both books, though!)

Hearne only veers off the path to happiness when she starts to protect herself from other people’s opinions and ideas by retreating into her own imagination. Eventually, she vastly prefers fantasy to reality. Every time she’s faced with a choice that might bring her back into the real world with real people, she condescends and retreats to the safety of her delusions, Don Draper-style — except without the expensive suits and the sparkling cocktails.

This year-long trial separation is a terrible thing for you. It means that you’re forced to experience all of the downsides of being alone — paying your own rent, worrying about what your ex is doing, haunting a half-single life while wondering if it’s your permanent fate or not — without any of the advantages. Trying on singledom for size is like “experimenting” with cohabitation. So much of the experience is defined by testing, by being on the fence, by wondering how things will go without making any concrete commitment, that it’s tough to get an accurate sense of what really being single or really making a commitment might look like. I’m not saying people should court briefly then marry. I’m just saying that it’s often much healthier to take clear action: commit to a partnership (which can be done without marrying) or don’t move in together yet. Break up or don’t. “Trial periods” tends to mean that one person has their cake and eats the other person’s cake, too.

Will you be happier alone? I don’t think you’re gathering new information on that front right now. Instead, you’re living in this limbo state that’s sucking all of the passion out of your life. As a result, you aren’t passionate about anything — not your ex, not yourself, not your friends, not the idea of other possibilities, nothing. In order to change that, you have to form a vision of your life that makes sense to you. Going out to bars all the time and/or dating someone much younger doesn’t make sense to you, so factor that out of the equation right now (instead of dragging your ass out night after night in order to avoid facing yourself).

Now tell me what does sound right. How do you want to be living a decade from now? What aspects of that picture are mandatory (must own your own place, must be creatively productive, must own a pet, etc.)? What aspects are optional? Do you want to get married? Do you want to have kids or adopt? Do you want to travel? Do you want to be involved in activities that don’t include drinking?

You need to decide what you want and set out in pursuit of it. If it’s really important for you to find someone and fall in love, that’s all the more reason to call an end to this so-called hiatus right now. You gave it 13 years. If your ex wants to make a passionate show of staying together (or you do), fine. Short of that, you need to call it quits and move on. The right plane can’t land if the wrong plane is blocking the runway.

Once you’ve broken up officially, then it’s time to commit to some activities that don’t feel lame to you. No one is going to make you start conversations. You just show up and take part, that’s all. We garrulous drinker types always imagine that every interaction depends on our performing for a live audience. No. Regular people just do shit (volunteer, join jogging clubs, throw poker nights) and slowly become more familiar to each other until conversations naturally happen.

You’re never too old to have the life you want. Truly. But you do need to know what you want first, and — maybe even more importantly? — you need to be able to say it out loud, without shame. I don’t know that you’re surrounding yourself with the kinds of people who find these sorts of direct statements socially acceptable. Is there a dearth of passionate talk among your peers? Do they mostly discuss what they don’t like, what they’d never stand for, who they would never want to be?

Fuck the meatless frozen entrees of the world. It’s time to be something, to own it, to announce it to the world without apology. Fuck the hipster hedging, the cleverness, the hiding. Stand up and tell the world what you’re made of, tell them what you fucking want — dearly, desperately, from the depths of your soul — and don’t accept anything less.


Dear Polly,

I will caveat the following by saying I’m not sure my question is exactly in the ‘existential/life’ category, but as a longtime reader (first-time writer!) I appreciate your generally incisive observations and hope you help me achieve some self-discovery through a different issue than those with which you usually deal.

So I’ve been dating this girl for 1.5 months. She is fun and cool and is super-cute and in great shape and is equally content dressing up for a night on the town as she is cooking at my apartment late into the night, laughing at my terrible jokes, and generally being excellent company. Extremely compatible in issues philosophical, religious, blah blah blah. There’s just this one thing. She has upper lip hair.

I classify it as ULH because it’s certainly not a full blown mustache — like maybe 10–15 hairs, short, barely visible by unaided sight, and then only if you seek for them desperately with a suspicious and jaundiced eye. I only really notice/am bothered by them when we’re making out — maybe I have sensitive lips or something, but I can’t escape the tingly tickle of these uninvited face-guests. It’s gotten to where it’s tough to focus on the pleasure quotient of kissing her because all my mind can do is scheme to avoid the bristly patch. As far as I can tell, she is either completely unaware of her ULH or is in denial.

I think it’s too early in the relationship and, given her pluses, is far too minor an issue to bring up now. But how and when should I? It seems like it’d be SO EASY to fix, and it’s such a minor roadblock it seems silly to not bring it up, BUT, if I were a girl, I feel (is this unjustified?) like I would be utterly mortified to be confronted about this, especially by a man I like and who I want to like me.

Am I a terrible boyfriend for even considering telling her about this? Am I being way too sensitive about her feelings? I wax my back and upper arms regularly (and did so before I met her) out of basic consideration for the fairer sex, and I am your average/not that sensitive/relatively brutish male. I’ve found women to be A LOT more touchy about stuff like this, so I’m kind of embarrassed for her to even have noticed it. Conversely, I, personally, would be deeply thankful and ecstatic for a girlfriend to say ‘Hey, you need to manscape down there a bit’ or ‘lose the scraggly top-of-foot hair, it grosses me out’, because its a super-easy way to make her happy. I feel like the rules are different, though, going the other way between sexes. Am I just nitpicking here? I need a wise woman’s help!

Thanks in advance –

A Hair Too Far

Dear AHTF,

Sweet Jesus. Of course I think you’re nitpicking. You youngsters won’t be happy until you’re as hairless as prepubescent aliens. Your shiny Caucasian bodies don’t scream “sexy” to oldsters like me; they scream Lair of the White Worm.

Still, I did just instruct LW1 to stand up and tell the world what she wants, without apology. And obviously this lip hair thing is messing with your passion in a big way. Even so, I don’t love how you wrote that you’re “kind of embarrassed for her.” She has no reason to be embarrassed, except for her embarrassment at dating a hairless white worm like yourself.

Anyway, if you really feel like you’re in this for the long-ish haul and you want to cultivate a nice, honest dialogue about what works and what doesn’t work for you, I would find some really humble way to tell her about YOUR problem. For example:

“This is really embarrassing for me to say, but lately when we kiss there’s something tickly going on… and I keep shaving my lip smoother but it’s still there. I feel like there might be some tiny invisible hairs on your lip that are maybe a little bristly? I mean honestly, I feel like an idiot saying this because I don’t SEE anything, plus now you probably realize what a ridiculous, exacting metrosexual fuck-wiener I am, which means you’re likely to dump me soon….”

Sorry for spelling it out, but I felt pretty sure you were going to fuck it up otherwise. (Yes, you can skip over that last part. That was just for you and me, baby.)

Anyway, if I’m being honest, my husband’s really bad haircuts and terrible, terrible pants downright haunted me when I first met him. It was like covering a really excellent steak with ketchup. I hinted here and there, but eventually, I had to speak plainly. Talking about it made me incredibly ashamed, though, because I knew these things were bothering me more than any healthy, normal person would ever be bothered by them.

Come to think of it, it wasn’t really about the haircut or the pants (although they were both truly terrible). It was about voicing something minor and stupid that mattered to me nonetheless. It was about admitting that he wasn’t perfect, and that sometimes, the things he said or did (or wore!) were going to bug me, and, me being me, I wouldn’t be able to keep my strong feelings to myself. So, when he reacted confidently, laughing off my pickiness without taking it personally, it was a good sign that the deeply irritating core of my bossy personality wasn’t going to cause him to break up with me. A miracle, truly!

Brand new relationships include all kinds of seemingly shallow and foolish trials, I guess. Who should I be to judge? (In contrast to the shallow and foolish trials of 13-year-old relationships, which are easily eliminated by breaking the fuck up already.) You sound like a nice enough guy. That said, though, if you successfully encourage your lady to wax her upper lip (or even just bleach it, which will make the hairs invisible and far less bristly), and then you find something else that’s unacceptable about her personal hygiene? Well, then you should probably give up on real woman and turn to the smooth, quiet, disinfected solace of blow-up sex dolls instead.


Are you longing for smooth, quiet, disinfected solace? Write to loud, filthy Polly for pointers on where to find it!

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.

Disturbing top photo by Shane Hirschman. Caterpillar photo by Donald Hines.