'Dating Is Making Me Doubt Myself!'

Sometimes men are so disappointing. But are my expectations too high?

The Garden Parasol (1910) by Frederick Carl Frieseke

Dear Polly,

I’m a woman in my late twenties, and I recently started dating again after getting out of a serious relationship two years ago. It genuinely took me those full two years to heal, which seems to surprise people, but betrayal is hard to come back from. To be clear, it wasn't just that this guy betrayed me - which he did, multiple times - but that I betrayed myself. I just completely abandoned myself and what I knew to be true, deep down, in order to love this person.

As I wrestled with the debilitating doubt I had about him for months and months, I also let other people convince me that I did not know what I, in fact, DID know: that something was off with him, that he was a cardboard cutout of a man, that his never-ending proclamations of love while simultaneously being the world's biggest piece of shit pointed to a serious internal problem. I can see now that I almost seduced these people into propping up my worst fears about myself. I wanted it to be me. I wanted to talk about how ridiculous I was.

When it finally ended, I made a promise to myself. I would never ignore the truth inside me again. I would be brave. But Polly, things already aren’t going well.

I’m now online dating (yes, it is terrible), and I recently matched with someone I was actually interested in. This is very rare, and I was excited. But the more I got to know him, the more I got this sense that he thought very highly of himself in that distinct, unquestioning way only a top-tier privileged member of our society can. However, this was over texting, and it's so hard to read someone you don't know over texting, so I told myself to wait until we could get on the phone.  

Once on the phone, things got worse. We talked for over an hour, and if you added up all the time where words were coming out of my mouth and not out of his, it would be... 10 minutes? Granted, I asked tons of questions, which maybe I shouldn't have done, but I really did want to know the answers to them.

Halfway through, I realized what was happening and told myself to chill on the questions. I let the silence hang. He took the cue and asked me when my last serious relationship was, as we had just finished talking about his. I gave him the short version, thinking he'd ask me to elaborate on something like I’d just done numerous times with him, but no, next thing I know we are fully back to him. And then there I am asking another question, which I feel like again is maybe my fault but also, I GENUINELY WANTED TO ASK THIS QUESTION because I wanted to understand him and know him. So yeah, that's how that entire phone call went.

When I got off, I told myself he was a nice guy and first calls can be hard and maybe he was just nervous. But as more days passed, I couldn't shake how much it bothered me that he didn't want to know more about me. Or how he seemed to like me more after the call, and how something about that felt really awful (I barely spoke!!). Later, he said a few things through texting that left a bad taste in my mouth, like when I asked him to tell me more about his only sibling, and he said, “Well he’s not as smart as me but he works harder.” Ugh. By the end of the week, I was over it.  

You would think that's where this story ends, but now I can't stop thinking about whether I'm wrong. Not just wrong about him, but wrong about me. Maybe I do expect way too much from people and think way too hard about shit. I have already made the mistake of asking people for advice, and everything they say makes me want to cry. "Men are just like that." "Men don't need to go into depth about things." "You're just going to have to find someone really, really special." That last one does make me cry, Polly. It makes me feel like I'm a fucking martian, and in this world of seven billion people, there are going to be, like, three attractive men that can ask me questions at the apparently ridiculous levels I require. Even if I did somehow find one of these guys, they would be destined to end up with women of similar rarity, so I assume, drop-dead Instagram models with perfect asses who are insanely intelligent and exceptionally kind. I can assure you I am not even one of these things.

I feel so doomed. I find myself dress rehearsing my life of never-ending solitude. I tell myself, “You need to get a better job so you can afford a better place, because there is never going to be a second income to help you. You also need to get a dog or a cat, because you're going to be lonely AF, and people with pets seem really happy. You also need to figure out how to have and enjoy casual sex, because casual sex will be your only option.”

I guess all of this would be fine if I didn't so deeply crave a life with a long-term partner. But Polly, I do. Even though I know marriage is bullshit! I know it's hard, and not like in that low-key glamorous way people say it’s hard, but like dark-night-of-the-soul hard. But I still want it. I want to spend decades with someone undeniably good and decent, someone with real integrity, and I want to work on shit and build a loving home and invest in a community and respect each other even when it feels fucking impossible.

I'm always going to want that, and it makes me unbearably sad that the only way I can have it (or a semblance of it) is if I lower my expectations. If I stop being so fucking intense all the time. If I stop thinking so critically about everything. If I focus more on being sweet and alluring when what I really value is being smart and fierce. If I give up some of my feminism. It's like I have to either give up myself or give up the love I always dreamed of, but how can I do that when they are two parts of the same whole?

I guess what I'm really asking are all the questions you've heard before. But I want you to give it to me straight, Polly. I can handle it. Are all men really like this? Am I the one fucking it up? Is someone like me destined to be alone?

Still Too Many Questions

Dear Still Too Many Questions,

Ask me ALL of the goddamn questions because I love you. You’re amazing just the way you are, never change a thing. You’re my girl. You don’t need adjustments. It’s all there. Don’t move that. Put it back. Yes, exactly, much better now! Motherfucking prayer hands, fire, exploding hearts, chef’s kiss, rocket launch, purple guy, send!

Let’s start here: You were on THE PHONE. Fuck the phone to infinity and beyond. Sorry, we’re going Old School Polly today because I’ve been through it lately and now I’m feeling myself. Who even talks on the phone to strangers? What’s worse than that? I get it, pandemic. I talked on the phone for two hours this morning, actually, but that was to my girlfriend who was holding forth on the value of walking right up to the scary edge of where you’re comfortable in order to learn something. My girlfriend is amazing, she needs zero adjustments. This morning she said something to me like, “Real connections have to be sustainable, they have to stay alive without the ventilator of fantasy.” THE VENTILATOR OF FANTASY. What god did I please that this woman fell into my life? I need to kill a goat for that guy immediately.

Now, if you were in person with this incurious fucker you spoke to on the phone, what would’ve happened? If you were sitting down in front of him, just the two of you, how would that look, do you think? Do you have certain ways of taking up space that other people seem to respond to?

Because I do. Put me in a chair across from a man, and he will have questions, oh yes he will. This isn’t about beauty. It’s about knowing what you fucking own, feeling it under your skin, all of your power, your ideas, your inventions, your heart. But you have to know who you are. That means you have to address your shame. Every problem you bring up in your letter — the bad ex, the unseeing friends willing to parrot your negative views of yourself, the second-guessing after the phone call — all of it is about shame. Knee-jerk, unaddressed, looming shame. You see your complexity and your sensitivity and your giant brain as liabilities. Understandable, in our dipshitty world. But THAT is what must change. You don’t have to change the whole world to change that.

I studied my shame and sat with it and addressed it and built from it repeatedly, and it took a while, but eventually, this strange power grew in its place. There are still remnants of shame, of course. Shame flares up unexpectedly sometimes. But now I fucking KNOW WHAT IT IS and I know how to say, “Oh yeah, this. I don’t have to sit and engage with this, this is not that helpful.” And I walk away from it. When that doesn’t work, I dig a little deeper and examine the underlying assumptions behind my shame. It helps to have my amazing friend who knows all about shame. But a lot of the people I’ve chosen to stay close to over the years understand shame really well.

Here’s what’s hard: Sometimes you have to know what’s up with you first, so you can teach other people about it. Remember how you taught your friends to see you as faulty and fucked up in your past relationship? You have to do the opposite of that. You have to learn some things on your own, and trust yourself, and build your own religion of who you are, and then you can (gently!) let your friends know about your strengths and weaknesses from a place of clarity, so they’re better able to help you talk through your lowest moments.

A lot of the stuff we try to hash out with partners and lovers and spouses is stuff that we should be hashing out with ourselves, and hashing out creatively, and hashing out with friends, and meditating on, and patiently examining every day. Curiosity and openness and trust in yourself make that possible. And that’s also where your power grows, a lot of the time: Alone.

I’m married and I love my husband, but I know how to grow power and make myself stronger on my own, too. I’m not saying that I’m not propped up sometimes. That’s how it is to be a human! But I fucking WORK REALLY HARD on my own, too. Complex, intense women and all sensitive people who’ve put up with a lot of shit over the course of their lives must do this kind of work, if they want to survive and be happy in our broken, fucked up world.

It’s not just about getting by on less, though. Don’t make yourself a beggar just because the world is a wreck. Build your power and enjoy it. That’s why people ask me good questions now: I don’t just have power. I savor my power. Important! In the old days, I didn’t notice my power as much, and when I did notice it, I was always tempted to feel embarrassed or guilty about it. I let it kick up my shame, because what kind of a woman savors her power? A vain, scary, bossy, bad, greedy woman does.

Fuck that noise forever. When you believe that kind of nonsense, you walk around monitoring other people’s faces constantly, to see if you’re fucking up. That’s no way to live.

Savoring my power has transformed my entire life. I’m way more at peace, and way more generous with other people. And I like to really relish my power in person – not that I would know, since we’re all trapped in our houses. *throws empty bottle at the wall*

Back to men. It’s not about looks. I am direct. I get to the point. I’m skeptical, openly so. I challenge a man. I squint my eyes at the stupid shit they sometimes say. I know I’m bragging right now. Kiss my ass. Let a woman brag. If that’s distasteful to you, ask yourself what you see as your rights. How small do you think you’re supposed to be and why?

It’s not that I’ve never kissed ass or followed some dude around or acted like an idiot. It’s not that delicate or passive or coy ways of being are somehow inauthentic. We can all be how we are, that’s all, and I just happen to be comfortable (and also a tiny bit pushy, for fun) in a conversation in person with a dude. The important part is: I am comfortable and I show myself.

Now, put me on the phone with that guy. Less amazing, but not terrible. Now: Make me send an email. I like writing, that one is fine. But then? Force me to text a motherfucker! Oh god, no. Get ready to be bulldozed by a sea of words. Just picture me walking at my treadmill desk while typing 120 words a minute, because that’s what’s happening. I text as fast as I talk. Maybe I text a little faster, because my brain works better on the written page.

I am really bad with text. I send too many words, too quickly. Very few people like it. My one girlfriend who said the thing about the VENTILATOR OF FANTASY (I mean this woman. Holy fucking god, this woman!), she loves my very fast words. She’s just on her phone but she texts almost as fast as I do. How does she do that? We can text for like 2 hours straight, all words, a wall of words. She asks questions, I ask questions. Metaphors! Madness! She’s a fucking goddess.

But don’t make me text someone I don’t know. I hate it, I’m bad at it, I might piss someone off five states away. I’m a fucking writer, too, so I want to edit myself. I want to double back and explain every single thing I might’ve been unclear about. I want to repeat very point five times. If you put me on “The Circle,” where they’re all just texting each other? They’d hate my guts and throw me out immediately.

But. If you set me up with a guy who likes women who have A LOT OF STRONG OPINIONS AND IDEAS ABOUT EVERYTHING, I could probably overcome these limitations. I might be able to win over OTHER GUYS in person, but the kind of guy who’s really my type would dig my shit in any format. And he’d probably even think I was hot, whether or not I was that cute at the time. That kind of guy craves access to smart, opinionated women. Luckily, there are a lot of guys like that in the world.

When I text or talk on the phone to the other guys, I feel weird and sometimes it triggers my insecurity from way back – the baby stuff, the feeling of jittery need, the feeling of being ignored. Texting with relative strangers is a tiny bit of a trigger, if I get a whiff of “Enough already!” I don’t like that. It makes me feel unlovable.

Sometimes I handle this unlovable feeling by typing even faster.

See, there are always remnants of shame. If I told this story and made myself the fearless hero who never feels discouraged or questions herself, how would that help? I’m pretty old, too. Shouldn’t I be bulletproof by now? Nope. That’s not how this stuff works. Remember what my goddess friend said? You keep walking up to the edge of your comfort zone because THAT IS HOW YOU KEEP LEARNING.

Ask Polly and also Ask Molly wouldn’t exist if I weren’t a lunatic via text and words on a page. I love to type faster and faster, compulsively, under pressure. You could say it’s sick, but I also dig it. It’s part of my personality. This is my fun. This is part of my power.

BUT. Put me IN A CHAIR with someone and I’m more human. I listen. I ask questions. I am calm. I don’t get triggered or fearful as much in those situations. God, I miss sitting in a chair, looking at someone, drinking and eating, being together and talking about whatever stupid shit floats along!

So you met a guy and you talked on the phone. (Fuck the phone forever!) Now he’s saying he’s smarter than his own sibling, and also lazier. Who is this piece of shit? Can you imagine announcing that you’re smarter than your own sibling? I mean, who the fuck cares? I feel like if you’re fixated on which of you is the smartest, you’re already behind the eight ball in the brains department.

The point is, screw this guy, he sucks. Of course he didn’t ask you many questions! He’s not interested in other people. He wants to compete more than he wants to connect (see also: sibling). Tedious! And let’s be frank, dudes like that are all over the place. But does that mean that guys who like intense, good-question-asking women with lots of ideas bouncing and whirring around in their heads are hunted to extinction? Fuck no, it does not. It just means that there are different kinds of guys, and you should never, ever take your experience with ONE TYPE OF GUY and use it as proof that you’re doomed and you will never find YOUR TYPE OF GUY because YOUR TYPE OF GUY hardly even exists.

That’s like walking into the zoo and spotting a single giraffe and announcing, “GREAT. THERE ARE NO ELEPHANTS HERE.” and immediately walking out. Actually, in your case, it’s more like calling the giraffe on the phone and asking him if he sees any elephants. The giraffe isn’t going to be that polite, since he doesn’t understand your language in the first place. But you’re still going to put down the phone and blame yourself for the fact that a giraffe at the zoo never learned English.

That’s what you’re doing now. You’re wondering if the giraffe you just called was an elephant in disguise. You’re blaming yourself for not being omniscient and also for not speaking giraffe.

Once you get into the realm of “I need special skills to find love,” you know you’re completely fucked. That’s shame: I have to fix myself up based on other people’s tastes in order to find love. Noooooooo.

You know what you need in order to find love? You need to talk back to your shame and tell it to fuck itself. And then you need to write down the first paragraph of my response on a piece of paper and tape it to the wall: You’re amazing just the way you are, never change a thing. You don’t need adjustments. It’s all there. Every time you see that note, I want you to GO AHEAD AND FEEL HOW GOOD YOU ARE. SAVOR IT. Imagine yourself sitting under that parasol in the painting at the top of this post. Scroll up there and look at it again. That’s you, dressed in white, reading your little book, satisfied. Do you need to change something for some dude who’s still being a wilty little dick about his brother? FUCK NO, YOU DO NOT.

That doesn’t mean everyone will love all of the time. Do people sometimes tell that girl in the painting that her face is too round? FUCK THEM. People who don’t understand a thing about you will ask you to change to please them. DON’T DO IT. Just get more comfortable with who you are and learn to stand up for yourself without making it someone else’s fault.

Will some dudes be uninterested or incurious when they talk to you on the phone? Sure, of course. Can I sink battleships with a single texting session? Absolutely. Can I make a lot of men interested in me just by being my obnoxious self in real life? I need you to fucking believe it, sister, because it’s the god’s honest truth. I cannot emphasize this enough: It is not about beauty or youth or coyness or even kindness. And could I make some of those same men anxious and repulsed if we were forced to communicate through a dating app? For certain, 100%. I can recognize that without letting it stand in the way of my power.

You need to get to know your power a little better. What works for you? What feels right? When are you en fuego? When do you start to unravel? Sometimes you’re a little messy and a little calm, but you just need a FRAME for your power, a way of getting on top of the facts on the ground, an angle, a way to connect with your truest self, a way to get into the zone. You need that moment in the game when Michael Jordan sticks his tongue out: He’s about to fuck shit up. You need to go straight into that space and live there and think about what you own.

You’re magical. Locate your power and frame everything with it, all of the time. Some men are giraffes and some men are elephants. You cannot fuck it up with the elephants. Everything you do is fine. You can’t even fuck things straight into the ground over the phone or text with them. It just needs to be an elephant. And who should you date? An elephant. Because elephants see you clearly. And who should you marry? Elephant.

This is why I love you, in part: You love working really hard. My only word of warning to you is this: Don’t work hard for a giraffe. Find an elephant. Elephants fucking love hard work. They adore it. The harder you work, the more an elephant will smile and sigh and want to stroke your hair.

Listen, I am way too much for a lot of people. Waaaaay too much. But a lot of people just love the ever-living shit out of me, and my husband is one of them. I can talk and type and text a massive tsunami of words at my husband and he just sits there happy to be drowning. He loves that my entire universe shifts every few days. He loves that I’m constantly learning new things by walking up to the scary edge of my comfort zone and peeking down the sheer cliff. He loves that I am super fun and assertive and weird and intense and he even loves that I have like three new friends that I talk about nonstop because they’re the best and I’m literally in love with them. My husband loves me the way I am. I don’t really overwhelm him with my tsunami of words very often anymore, because I like my own company a lot and I also have lots of elephant friends.

There are tons of other elephants out there. I found my elephants by showing myself and not giving in to my fears and self-recrimination, which are BIG and always have been. Finding my elephant husband is NOT the most important part of my story. Because with or without a partner, you’ll grow happier and happier as long as you learn to address your shame and also own and savor your power.

So figure out a way to frame yourself (for yourself!), so you can keep showing yourself. Don’t analyze why the giraffes are skeptical or hold back or don’t ask questions. Just find the elephants. Befriend the elephants. Enjoy the elephants. Celebrate the fact that you’re an elephant, every single day. Trust yourself, and show yourself.

The only tiny caveat I would add is this: When you start feeling a little triggered, and you start speeding up, and you’re feeling jittery about where you are? Slow down a little. Take in the moment. Stop working so hard to fix things. Put yourself under that parasol. Remember your power. And never, ever try to coax a giraffe into becoming an elephant. You’re magical, but you’re not a magician. Neither am I.


Heather Havrilesky is the author of three books, most recently the essay collection What If This Were Enough?, which was a Publisher’s Weekly Best Book of 2018. You can read Heather’s most recent Ask Polly column on New York’s The Cut, where it’s published every other Wednesday. The other Wednesdays, Ask Polly will live right here, so sign up, it’s free! And don’t neglect Molly. Send your questions to: askpolly at protonmail.com.