Here's the Thing: Will I ever have a girlfriend again?


Hey. I guess I'll start with the pleasantries and see how crazy things get from there. Gosh. I'm already starting off on the wrong foot (I'm really only weird, I promise. But also bipolar, so maybe a bit crazy.) Anyway, shit. Not how I wanted to start this. I'll move on to those pleasantries I mentioned. Pretend those first few sentences never happened? Ok. I think I might just be stalling, so I'll get into it and rip that bandaid right off. 

I'm 35 and I haven't been in a relationship since I was 21. There. I'll let that sink in for a sec...

Fifteenish years of no girlfriend. Not one. In fact, last time I had a girlfriend I had to teach her how to text. I'll let that that one sink in too. I had to TEACH HER HOW TO TEXT. We didn't all have T-Mobile Sidekicks and T9 sucked. Anyway, you probably get why I'm writing you now. I'm one of the shitty ones. That's not to say I didn't try to get girlfriends. I had crushes, went on dates, did some horny things, and texted, "You up?" But nothing ever really ever materialized into a relationship. I don't think I've been in love since the one that got away in 2006. I got close, but it turns out you both have to be into each other. So not fair.

I wasn't the worst looking tool in the shed, but I was also never the hottest bull in the China shop. I'm more like the friendliest, but least confident broken blue crayola in the 1st grade crayon bucket. And now, well lets just say I haven't aged well. I've put on 60 pounds (actually 80ish, but just lost 20) and lost enough of my hair to wear a hat every time I leave the house. If you're into scales then I'd say I'm a solid three, maybe even a four if I've trimmed the beard and just did the laundry. But like I said, I gained 60 pounds so I'm not really that into scales.

It's not just the way I look and the low self esteem that I'm worries me. Believe me I could keep listing reasons I'll be single forever. It's just that I dont want to be. Being single sucks and I'm tired of going home to no one. And making my road trips alone. And eating fast food every day because it's the only thing I know how to cook. Sorry, down with the patriarchy, I get it. I just don't want to eat alone anymore but I'm absolutely clueless when it comes to getting someone else at the other side of the table. And since it's been so long since I've had a girlfriend I really don't know what an adult relationship is like. I've never argued about bills or complained about the in-laws and how her mom takes that dumb dog everywhere. I don't know the rules or what I'm doing, so am I destined to live this life forever and put on another 60 pounds? I probably am. I just wish I wasn't. Is it even possible to stumble accross some lady that is willing to put up with my relational ignorance? Who wants to teach a 35 year old man how to boyfriend? I'm guessing no one.

That feels like a good stopping point. I wanted to tell you about how my last date ended with her agreeing to meet me at a movie and then never showing up and then me not realizing I got stood up until after I bought the tickets and then finding out she blocked me so I couldn't even be like, "Hey my feelings are hurt. Yeah I'm 6'3 but I'm also a fragile little boy in an overweight body who's out $12 and watching Once Upon A Time In Hollywood alone."

I wish someone could explain to me why I find stock photos so funny. I’m sorry. I just do.


This took me a while to think about how to answer, and I want to note that what comes next might be painful to read because I’m going to be very blunt with you.


There is a lot going on here. Most of what I see here is pain. Pain of loneliness, pain of insecurity, pain of rejection. All of us—all!!!!—feel those things from time to time. Some feel those things a lot. Some feel them near-constantly. They are horrible, wretched emotions that make us feel small and scared and vulnerable and valueless, even if we really aren’t.

I had to take a class once in order to be an R.A. at my college (didn’t end up doing that job, but the class was delightful) and one thing we learned is that one of the most important things for humans is that we feel we matter. Of course, in our world, a large part of that can and often does come from romantic relationships. I’m not going to lie to you and pretend like these relationships aren’t valuable or try to condescend you by saying that you simply should stop caring about them. OF COURSE YOU CARE. It would be impossible to be able to shut off that longing of yours, so I will in no way suggest that you try to do that.

With me so far? Ok, here comes the bad/hard to read shit. If you want to save it for later, I completely understand.

I think you need to do some grieving. You (perhaps paradoxically) have made very little space in your life for actually grieving the sadness and pain you’re carrying everywhere. It’s like you’re wearing a sandwich board that says “I’m desperately lonely and sad,” around and hoping someone else will simply take it off of you and chuck it into the street. HOWEVER, in the meantime, you refuse to acknowledge, deal with, or talk to anyone about either the fact that you’re sad or that you’re wearing a massive sign that says so. You have to take a break from your desperate longing for a partner (a fact which you’re likely fine with most of the time—that doesn’t make it not desperate or not longing) and you have to grieve. You have to allow yourself room to actually address the sadness rather than simply being sad. You have to say to the mirror or write in a journal or talk to a therapist about the fact that you’re upset that you haven’t dated for 15 years. You have to say what that feels like. You have to grieve what you feel you missed out on. You have to MOURN.

BIG NOTE: 🚨 You cannot mourn to people you are trying to date! 🚨 You absolutely can and should get support. (Please consider a therapist if it’s an option for you. Please). But right now you’re asking for someone to come along and fix the sadness with their mere willingness to date you. That’s like asking someone to fix an abandoned house with a Clorox wipe. ANOTHER PERSON CANNOT DO STRUCTURAL WORK. They cannot mourn for you, and in the early stages of dating they cannot be your repository for your grief and anger over other people not dating you. I suspect it has not occurred to you that you’re handing this burden off to other people. Maybe you’re thinking I haven’t even gone on a date with anyone, how can I be putting my emotional shit on them??! Well, sadness and desperation are are like eating a tuna sandwich on a plane: everyone can tell. We all know.

If you don’t do this work ON YOUR OWN to grieve your sadness about being single these past fifteen years—which is perfectly fair to be sad about— you are going to go deeper down the anger-at-potential-partners spiral. I know you meant it as a joke but you literally complained about someone not loving you back as “unfair.” It’s perfectly fair! People are ALLOWED to not love you back. It’s not cruelty for someone to not want to date you.

Dating begins before the date. It begins with attraction. Before you even get on dates, you are giving off the impression to people that you are going to ask them to do your emotional work. Which again, they cannot do. It seems to me that you have the common—but misguided!!!!—impression that the reason you aren’t dating has everything to do with how you look.

That is a part of dating. I’m not going to pretend that everyone should be attracted to everyone else and if you aren’t, you’re a shallow twat. There are going to be plenty of people who you’d like to date who will dismiss you because of how you look. THIS HAPPENS TO ALL PEOPLE. (Other than like Kerry Washington and Gemma Chan). Yes, there are some people who have WAY more options because they’re banging hot. No matter what that will exist. Not everyone will want to date you. Not everyone wants to date me. Not everyone wants to date fucking Brad Pitt. Your body is not at fault for your lack of dating; you have to get over that idea!!!! It would be nice to pin it on your body because then you could focus all your hate and rage at your personal meat cage that you’re trapped in but I’m not going to let you get away with that. It’s reductive and rude to yourself. YOUR BODY IS NOT THE PROBLEM IN ANY WAY. If you feel like adopting healthier habits, fantastic. If you don’t or can’t, that’s ok. But stop punishing your body for not having a girlfriend.

What I think does need work is the way you communicate and relate to people. I know this seems like an aspect of simply Who You Are, but it is not fixed. It can be worked on. Saying that it will be fucking difficult would be a massive understatement. It will be excruciating. But if you’d like to date some day, I think it is required.

Your letter to me was full of self-deprecating jokes. I know—from years and years and years of personal experience—that it seems easier to make a joke about yourself before anyone else can, so that way at least you’re in on the joke. That is wrong. It’s wrong because it inherently assumes that everyone wants to insult you. It assumes that you suck and someone has to be the one to make fun of you so it might as well be you.

Imagine if someone baked you a cake and then was like, “Don’t eat the cake it fucking tastes awful. Seriously, don't eat the cake. I think I put salt instead of sugar in there, you’re going to hate it. Please I’m begging you, the cake sucks, do not try it.” And then they got upset later because you didn’t try their cake. You’d be like… what the fuck??!?! You put people in an impossible situation when you desperately want their approval while insisting that the thing you want approval for sucks shit.

Right now, each interaction with you is you begging people to validate you for long enough for you to get to the next validation. That is exhausting, and you cannot cover it up with jokes. The jokes do not work, they just make it more obvious. It’s like putting duct tape on a scratch on your car. And behind a lot of your jokes is a bitterness that other people don’t like you (which you don’t know yet, but you feel sure of).

You do not need to learn how to be in an adult relationship, because there is no one single way to be in an adult relationship. You will have to learn how to be good to the person or people you end up dating. You will have to learn to not blame them for feeling lonely before them. You might mess up; we all do. Someone might break up with you, and you will have to learn how to not internalize that as a failure (even if it feels like that). It’s simply part of the dating life cycle, and if you’re going to date, you have to experience it.

You need to learn who you are and how to like yourself enough to interact with other people better, so that you aren’t putting your insecurities on them. You need to learn to put down your security blanket of self-hatred long enough to pick something else up, something joyful. I am not suggesting that if you love yourself all of a sudden other people will flock to your cock. That’s a bullshit thing people say. But right now, no one can get joy around you, or fun. They can only get acerbic, self-hating jokes about how much you suck. Which isn’t true, but it also isn’t appealing to fall in love with.

WHEW. Ok. The hard / bad part is over!!!!!

You are lovable. You are worthy. You may be single for a while longer and it may hurt a lot. It doesn’t mean it will be forever. Try your best (although it’s hard and frustrating and annoying as hell to hear) to fill your life up as much as you can with things that are good for you. With friends that are kind, hobbies that make you happy, and habits that care for yourself. As you well know—but perhaps don’t like—life does not begin when you get a girlfriend. This is life, too. Be gentle as you grow, because growth is painful and sucky. It’s also necessary.


Sophia Benoit writes this very newsletter; she also writes about sex & relationships for GQ, tries to write about Fleetwood Mac for GQ, avoids writing by tweeting at @1followernodad, works full-time as a researcher for Lights Out With David Spade, and has had bylines in The Guardian, Reductress, Refinery29, Allure, and The Cut. You can reach her or yell at her at