Ask Polly: I'm 33 And Single. What Am I Doing Wrong?

Hi Polly.

I’m not really sure why I’m writing you. Actually I am. I need to feel ok with being single at 33 while still maintaining hope that I can find a solid, real, lasting relationship. Every time I read one of your columns on this subject, I feel empowered. I apologize for being unoriginal but this stuff is hard and I am at a loss!

I embrace being single. I appreciate being on my own and dictating my own schedule, I do a ton of yoga and look great (might sound conceited but it’s true), I own my own successful business, I own my condo, I save money, I travel and pursue things that are interesting. I have an adorable, silly cat, dammit. I believe strongly that I can’t and won’t settle until it’s RIGHT.

I’m admittedly scared that that conviction will keep me from being in a happy relationship because I’m asking for too much or won’t know “right” when I see it. At the same time, I seem to keep getting hurt. There’s a pattern—I date a guy for a month or two. In the beginning, it’s always him pursuing me hard. And then I let my guard down and start to like him, start to think about a future with him, and then, like clockwork, he backs out. I really don’t understand. I know that you have said over and over that we shouldn’t try to draw some sort of conclusion about rejection, but I am struggling here!


Most recently, I was seeing this guy that I was very interested in. True to form, he worked hard to date me while I was not so sure at first. After about a month and a half, I thought things were going great. I had to go out of town for 10 days, for work and to take care of my mom who’d had major surgery. We texted or called each other every day when I was gone. When I got back, rather than making plans to hang out for an evening, he wanted to stop by for sex on the way to a party that he “had to make an appearance” at. I suggested hanging out another time when we could actually spend time together rather than be rushed. He said he understood but basically I never heard from him again.

Maybe I hurt his feelings? I made it clear that I wanted to see him, just was not really ok with those circumstances. I love sex but I felt like a “layover” (ha, ha) on the way to his obligation or good time. I knew he’d been busy at work but in his shoes, I would have made time, invited him to the party, not gone, something else. Logically I know that this guy did not treat me right, or at least was not “into me” enough to work with me and honor my feelings. Even though he put a lot of time in in the beginning—hanging out every day, calling and texting all the time, telling me how much he liked me, etc., etc. The worst part is that I still really like him! I can’t shake the idea that I was too demanding or inconsiderate.

Am I trying too hard? Not trying hard enough? Do I need to lighten up? Be more blunt? Do I get attached too quickly or not quickly enough? I’m really trying to just be myself and see where it takes me, but these little episodes where I date guys who disappear is messing with me. They make me question how great my single lifestyle really is, question my approach to dating, get my hopes up and let them down. On the other hand, I know I need to be open to risk in order to get what I ultimately want, which is long lasting love. How do I reconcile those two conflicting feelings? I also have this weird idea that if I just get past the first few months, I can make things RIGHT if I like the guy enough. I feel like a failure that I can’t even get to that stage! That has got to be completely wrong but I don’t know how to change that thought process.

Maybe Doing Something Wrong

Dear MDSW,

One of the major pitfalls of being single is trying to apply all of the principles that work in other parts of our lives to the problem of love. It’s natural, of course, that you’d think that the same hard work that you’ve done to start your own business, buy property, and stay fit and healthy would somehow translate to finding the right person. And I don’t even mean that you’re doing that, exactly. I mean that you have some notion of agency and control over how things will go with any given guy. You write, “I have this weird idea that if I just get past the first few months, I can make things RIGHT if I like the guy enough.”

You have to lose the idea that your big challenge is to “get past the first few months.” Like somehow you’ll never MAKE ANYTHING WORK if you can’t CLOSE THE DEAL or at least PREVENT the deal from being prematurely closed during the first few months.

Studying past failures or analyzing the point at which things fell apart, repeatedly, in the past will NOT necessarily tell you anything about what you’re doing wrong. You simply haven’t lucked into finding the right guy yet. That’s all. We can’t overhaul your management style on this and secure more success. You simply have to stay open and play it as it lays.

Personally, I was always great at getting past the first few months. I liked hanging out, shooting the shit, letting the day unfold however, watching football, ordering pizza. All of the lazy things I would never allow myself to do when I was alone, I would do around a boyfriend. I compartmentalized my feelings well enough that a dude would see a very easygoing, witty, anything-goes personality for a long time. A bad bout of PMS might threaten to rock the boat, but then I’d essentially apologize and pretend I didn’t expect to be met emotionally and go back to hang out mode fast enough that I’d cover my tracks.

Eventually, though, I’d start to put on some pressure, plus my façade would break down and I’d start getting intense or weepy or weird at the drop of a hat. Boyfriends would wonder if this was the new normal. I’d wonder whether we were really a good match or not for the first time, but I’d still keep trying to MAKE THINGS RIGHT. I was really good at making a mess and then making things right, basically maintaining the status quo while I got more and more depressed over the dead-end nature of each relationship.

By a year into it, I’d feel pretty dependent. I wouldn’t be putting the same energy into friendships or my career or anything else. I would set everything aside to hang out. Without the dude, I knew I would feel lost and lonely. But the dude was usually looking less and less like my one true love to me by then.

Do you see how much time I used to waste with the wrong guys? You aren’t doing that. Do you know how many times I would’ve been ok with that layover offer? I might’ve made it obvious that I was the perfect person to take along to that party afterwards, but all that means is that I had a bulletproof social pitch at the time, one carefully crafted to appeal to your typical breezy, Mr. Flinchy nowhere man. You have a life, a job, a condo, a cat, friends, travel. You aren’t going to serve up drive-thru sex to a guy who’s on the way somewhere else. The idea that having principles like this, and living your principles, could EVER be construed as demanding or inconsiderate is totally laughable.

It’s also a testament to just how hard it is to be a single woman in your 30s. You have collected data. And as a smart, hard-working woman, you are naturally going to use that data to determine WHAT IS WRONG WITH YOU.

You liked this guy. He wasn’t right. He wasn’t right because he missed you and then he wanted to stop in for sex instead of taking you out for a quick bite first, then going by the party, knowing that you’d both be in the mood after. To put it on the table like that, to say “I want to fuck and then leave to do this other thing.” Or even “I want to fuck and then we’ll go to this thing after.” No. Shit, he could’ve said “I need to see you right now!” and come over and things would’ve happened and then he could’ve invited you to the other thing, or you could’ve had dinner or whatever. I’m not saying he should’ve been more coy, but let’s face it, there were plenty of ways he could’ve gotten exactly what he wanted AND not blasted the impression that he might just be in love with you clean out of the water once and for all. Did he care about the impression he was making? Clearly he did not. That’s all the information you need, and it has nothing to do with what YOU did after that.

His disappearance is a moot point. You merely indicated that you weren’t a fuck buddy, and he scrammed. This is how it was going to end. He’s attracted to you, that’s all.

My guess is that lots of guys are attracted to you, so you’re going to have to meet a greater volume of guys just to find a few who are legitimately interested in who you are. It’s not HOW YOU SIFT THROUGH THEM that determines whether this or that dude is truly interested or uninterested. Sadly, you don’t have that much say in the matter. But it’s actually freeing to realize that. You are sifting by staying strong, by not compromising the things that are important to you, and by not being afraid to say “No, thanks” when you get an offer that you ABSOLUTELY CAN AND SHOULD REFUSE. I know it feels like you “messed up” because you really liked this guy. I know that feeling well. But you didn’t change the outcome. If it were me, I would’ve invested two years and thousands of dollars in couples therapy and THEN I would’ve figured out that I was with the wrong guy. God, it makes me tired just thinking about it.

So here’s the bad news: You just have to stay open and know that you’ll find the right guy eventually. You really will. And it won’t be hard to tell if it’s right or not. If it’s super hard to tell? It’s not right.

The taxing thing is that every time we meet someone who’s fucking great, we say, “Is this right? Where should I compromise? What should I say to this? Am I doing that old bad thing I do where I ask for what I want and ruin everything again?” The stakes shouldn’t be raised just because someone seems really smart and funny and nice to look at, and you decide you really are interested, and they work really hard to date you. But they do. In theory, you should be able to say, “I’ll know if this is right if he keeps asking me to dinner and listening and treating me like someone he might really love.” You should be able to remain a little detached, until it’s clear that a guy really does care and doesn’t view you as a conquest. But who can do that? It’s stupid to even expect that of yourself, honestly.

You say guys pursue you really hard at first. Are you clear with them about who you are at that point? I don’t mean “Hey, I want to get married soon” but “This is who I am. You might not be the kind of person who wants someone like that.” Even that sounds strange, I know, but there are these opportunities when you’re dating, to either appear lovely and demure and sweet and to encourage the continued pursuit at all costs, or to be frank about who you are. This is just a stab in the dark, but it’s possible that if you flashed a few flaws a little sooner, you might get a sense what the guy in question is ACTUALLY after: a real human being, or a very attractive woman who WILL SLEEP WITH HIM EVENTUALLY, DAMN IT! I know I sound like a crazy person, suggesting you show your flaws at the very outset. And certainly when you start repelling dudes straight out of the gate, that’s not going to convince you that you’ve got the moves like Jagger.

BUT I have to tell you, there’s some really good swaggery carpe diem feeling that comes from asserting who you are, for better or for worse. You should maybe experiment with it. Hanging back and watching how hard he’ll work to get you can be a crafty maneuver that leads to short-term success, but it’s also a little bit traditional and (somewhat paradoxically) it appeals to a more predatory macho style of dude. It gets all of his CHASE THAT BUNNY RABBIT juices flowing. Useful, I guess, if that’s what you like. But given your smarts and your overall empowered, I Know What I Want deal, the bunny chaser is maybe not your target demographic. You maybe are looking for a sensitive guy who really loves real human women, not bunnies.

I do think, also, that—oh god, now this is really the stuff of shitty women’s magazines and heteronormative nightmare trend pieces—but I think that having it all can be a stumbling block for men, but it’s a stumbling block for the kinds of men you absolutely don’t want in your life. Your general togetherness and attractiveness, when paired with a cautiousness and quietness upfront, is really fluffy bunny ass for a traditional man. When you show your sharp bunny claws, though, this kind of man is going to turn cold and turn tail and run. The magazines will tell you to fluff up your tail and play down your giant brain. I’m going to give you the opposite advice. If I were you, I would try flashing the bunny claws earlier, to see what you’re dealing with. Is this a bunny chaser, or a guy who likes real assertive happy human women? Mutter a few ribald remarks, make your opinion crystal clear, then look the guy frankly in the eye as if to say, “That’s me, buddy. Like it or lump it.” Many, many men with an eye for a princess will get gone real quick-like after that.

And I know, I know, I know that plenty will read this and picture a kind of gauntlet-throwing hot-tempered wretchedness being inserted into a perfectly nice mix. But that’s not what we’re talking about here. I mean, I’m a personal fan of gauntlet-throwing hot-tempered wretchedness, sure, but that’s neither here nor there. MDSW, I think you understand what I mean by borderline bold statements and some advertising of flaws and open eye contact and clear boundaries, paired with interest and kindness. I think you might just figure out that you maybe are a little controlled and stiff around how present yourself at the outset. And I think you might just see that what you want is NOT to make it past the first few months. What you actually want is to fuck things up BEFORE then, so you can move on to the guys who aren’t just engaged in an elaborate chase to get some high-end tail.

So that’s the only thing I’d ask: Are you making it clear from the start that, not only that you are NOT remotely perfect, but you’re not for everyone? You are who you are—assertive, frivolous, angry, effusive, messy, exacting, hopeful—and you want something real. It’s funny because most smart women are ALL of these things. And sometimes just saying so will scare away the guys who want someone who prefers to pretend and stoke the mystery, and will attract the guys who find honestly and flaws and vulnerability and toughness mixed together incredibly romantic. It won’t change who you’re dealing with, it won’t turn Mr. Wrong into Prince Charming. It will simply save you time by clearing out the escapists and macho chasers who aren’t into egalitarian relationships and female complexity and real life.

God bless the bunny chasers. And if you’re a bunny, god bless you, too. I know people who really love that whole picture, for sure. I don’t personally know how to navigate it, so I can’t offer much advice to those who prefer it.

But I don’t think that’s what you want. So I think you should stop focusing on what you’re doing to fuck things up so early, and focus on fucking things up earlier, thereby sorting out the clunkers before you’ve invested your emotions too much.

Other than that? You have to be optimistic, be patient, write down everything you’re grateful for every night, and remember that you will look back on this time as one of the most important times of your life. You’ll look back and feel really proud of how you conducted yourself, how strong you stayed in the face of your loneliness, and how much you appreciated what you had. It’s true that you could be in this place for 2 years or 12 years, and even so, you will look back and feel good about it if you play your cards right. It’s amazing to have your own business and your own place and your own cat. You are living the good life, for sure, and while it’s great that you’re open to finding love (which takes its own kind of effort) nothing that happens on that front should undermine how satisfying and hard-won your happiness is right now. You have to believe in your life and romanticize it as much as you can. Remind yourself to feel proud of what you’ve built, and what you’ve overcome, every single day. And feel proud of your flaws and your loneliness and your big heart, too. It’s ok to feel vulnerable about wanting love and not finding it. That vulnerability will lead you to good places, even when it feels like it’ll topple your apple cart. You don’t have to be perfect. Let yourself be a little weird, a little uncertain, a little brash. Let yourself get a little messier. Let your seams show. Be proud of your broken pieces. They’re the best part of you.

Don’t speed through these days to get to the good part. This IS the good part. Savor it.


Are you trying to savor the good parts, but you can’t do it, thanks to fucking Candy Crush Saga? Write to Polly and spill 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. Photo by Rick and Brenda Beehorst.