I can't keep a man.

It's hard to not feel like I'm trapped in a vicious cycle, like there's some sort of divine influence here and I'm just not MEANT to be in a relationship.


To paraphrase a 1990s Cosmo-style magazine: I can't keep a man.

I'm a 28 y/o straight woman who's living in a big city. I have a ton of friends, a good social life, a fulfilling creative job, a writing course I'm completing on the side, and a really nice flat I share with a friend. I work out a lot, take care of my health and hygiene, make the effort with the way I dress. I get told that people look at me and think I've Got My Shit Together. And I'll take it - I've worked hard, I've had a pretty chaotic time in the past but I'm in a good place right now.

Throughout my life I've dated a fair few guys and had a couple of self-defined relationships, but my average relationship duration is only around four or five months. I've had some very intense friendships-bordering-on-relationships for longer periods of time, but when it comes to solid, consistent, hand-holding lovey-dovey romcom relationships, six months has pretty much been the cut off. I've never met a boyfriend's family, I've never been on a romantic mini break, I've never lived with a boy, hell, I've never even celebrated Valentine's Day with anyone. When I was younger, this was a little confusing, but nothing to really worry about - now, it's starting to feel pretty lonely.

I don't think any of my relationships (or flings, or pseudo-relationships) have been particularly unhealthy; I'm on good terms with all my exes, and some I consider good friends. I recently started seeing a guy quite seriously and found myself getting privately nervous as we approached the five-month mark - to my relief, we passed it, and he still seemed super keen and interested, until suddenly, six months in, I'm dumped. It's usually the same story - "you're too good for me, you deserve something better, it's not you it's me", etc etc - and I find myself with no ability (or too much pride?) to fight my corner. I often get the sense that my friends and colleagues on the outside look at me and think I just need to be patient and to hold out for someone TRULY awesome, that these little relationships are just bumps in the road, but I'm starting to worry no such person exists.

A few years ago I got my heart broken pretty badly, while two of my friends - let's call them Jill and Jane - also suffered similar experiences at the same time (Jill's was a clean break-up, similar to mine; Jane's was super messy). I remember all three of us held out hope that our respective men would suddenly change their minds and turn into wonderful boyfriends. I knew we were being naive. Except! That DID happen for both Jill and Jane - the men came back, changed and brand new, and they're now both in relationships with the same men who completely adore them. I found myself with a glimmer of hope: would my guy do the same thing? But then there's always that other voice in my head: no - it never happens to you and you know it. And I was right - my guy moved on and I was left alone.

I don't expect you to diagnose what I'm doing wrong, but I'm hoping you can help me change the way I feel about it. I've always been perfectly happy being single, always with a full life and only letting men in when I felt they could really add to it - now, for the first time, I feel miserable seeing my friends hit milestones in relationships while I either date men who drift away from me over time or simply ghost.

It's embarrassing for me to write this, as I've always taken pride in being someone who doesn't need a relationship to feel happy. But is it too much to want to go through the same thing as everyone else? I'm worried by the time I actually get around to dating someone for long enough, I'll be so inexperienced at such a late point in life that I'll make all the wrong moves, or I'll end up in a shitty relationship I'm too scared to duck out of. And it's so hard to not feel like I'm trapped in a vicious cycle, like there's some sort of divine influence here and I'm just not MEANT to be in a relationship. How can I make myself feel more positive and optimistic about this?


This is a mountain in Peru called Vinicunca and it has nothing to do with the letter, it’s just beautiful. Bless.


There is a massive—MASSIVE—difference between needing a relationship to make you happy and feeling lonely. One of the minor shitty parts of women making (insufficient) gains in this world in terms of career/education/rights is that we’ve somehow convinced loads of people that the options are either/or. Either you have a career and are a—pardon me while I vomit—badass boss lady who doesn’t need a relationship OR you’re a simpering fool who has owned her dream wedding dress since she was 14 and can’t imagine a life larger than being a housewife. I don’t know anyone who lives in that binary and likely neither do you.

Everyone needs love and most everyone wants romantic love in some form or another. Romantic love—as part of some banana pancakes misunderstanding of what feminism was about—has long been scorned as being “small” or “vapid” to want. We all went a bit too far on the backlash against traditionalism and housewife expectations and we got to this weird point of, “You can’t even say you want love without seeming weak or daffy.”

I do think we’re getting a bit better about this in general, that the stories we tell about romance in general and women in romantic situations in particular are getting more generous and nuanced. But I think the patina of these judgements remains.

So! My advice to you is this: LET YOURSELF CARE ABOUT LOVE!!! Let yourself feel lonely without beating yourself up, for fucks sake! Of course you’re feeling left out— a lot of your friends are doing something fun and thrilling and lovely and you’re not right now. How could you not feel something about that??!!

You’re stuck in a denial of how you’re actually feeling because you don’t want to feel that way—which is normal. Who wants to feel lonely or left out? Who wants to feel abandoned or defective? Those feelings suck!!!! But also, they’re part of being human and you can’t possibly get past them without going through them. There is no cheat code or advance to Go and collect $200. I’m sorry; it’s very bullshit.

I’m not suggesting, by the way, that you ought to feel any of those things— it seems in the past you’ve been single and not felt them. Great. That absolutely happens! But sometimes you’re going to be single and hate it and that isn’t because you’re weak or small minded. It’s because you’re lonely. God bless you for being lonely, for wanting human connection. Everyone does; have the grace and the boldness to admit it to yourself and like that about yourself just as much as you like that in the past, you’ve been totally ok to be single.

As a bit of a separate note: Not that you specifically asked, but I do not think that you should have “fought” for your ex to stay with you. I’m most ardently against people having to convince someone to stay. I’m not suggesting that all good love is easy all the time, but the bare minimum should be that the person wants to be with you. They may muck it up now and again— you will, too. But by god, the person shouldn’t need to be cajoled into putting in effort. Ever. Disinterest is a deal breaker!!!

I know you’re not looking for me to diagnose what’s “wrong,” and I’m certainly not going to— I couldn’t even if you did ask for that, frankly. I have no clue. But I do think you might want to do some work around it. Please do not misunderstand me here; I do NOT think you need to go on a bear hunt for one specific Flaw that you have that has made every man leave you at the same point of the relationship. That doesn’t exist!!!!!!!!!

There is most certainly a chance that all of these relationships ended around the same time coincidentally. Perhaps relationships in general either get more or less serious around the five / six month mark, and yours all happened to end. I don’t know.

What I mean is that you need to figure out what you want and how you want it to look. This may have changed since the last time you were perfectly happy being single. You need to figure out who you want to be and the life you want to life. And you need to take a lot of control while you’re the only one driving the ship. One of the best parts about being single is that you have so much space and ability and power to make changes both large and small without having to account for almost anyone else (obviously family + friends still matter in huge albeit different ways). Take that power and decide what you want out of life and what you want your next relationship to look like.

If you don’t do this, if your only measure for success of a relationship is its length, or whether a person stays with you, you will end up in a relationship with a person you don’t give two shits about. You probably won’t even notice right away. You’ll hit month seven and eight and think, “Wow, this has lasted longer than anyone else.” You’ll hit year one and think, “I can’t believe I made it to a year.” And then you’ll hit 16 months and think, “Fuck I don’t know this person at all and they’re kind of boring and we don’t have much to talk about now that the honeymoon period has worn off and I’m not sure that this gives me anything in my life.”


Do not let the length of your dating someone be an accomplishment. The accomplishment is treating people well and finding people who treat you well. The accomplishment is two people doing the work together. That might last 10 months, that might last 10 years, and that might last 10 weeks. Length of a relationship certainly helps with intimacy, but a relationship isn’t more worthwhile or real because it lasted 40 years. I know plenty of people in very unhappy yet long marriages who can attest to this. When you do get into your next relationship, do all the work you can (and it will be tough) to not count down the months/weeks/moments. Enjoy what you enjoy.

You will not mess it up by being too “inexperienced,” because that is not a thing, really. At least not in the way we’ve all been led to believe. All relationships are brand new to both people. That’s like assuming that someone will be good at running an ice cream shop because they’ve been a forensic accountant before! You guys together get to decide what the relationship is like. You’ll learn what works and what doesn’t slowly and uncomfortably together, which is how all relationships unfold. You are not losing any skills!!! The “skills” required to be in a relationship are things like kindness, respect and patience. You have those in spades.

So: first do some feeling and then build up your life. Feel sad, feel mad, feel lonely, feel bitter. Whatever you feel, actually feel it! If you have the time and money to go to a therapist and rage/complain/cry/ask questions about this topic, I would strongly recommend that for you. This is a hard topic to talk about with friends very often without it becoming loaded or unhelpful. The therapist is there to take some of the burden from loved ones, not because I think there is something deeply wrong or dire about the situation you’re in.

Once you’ve felt some of your feelings, then you have to address those feelings with actions that get at what your fears are/ what your grief is (e.g., cried, sat in a sauna for a few hours, gone on a trip alone, started taking singing lessons, etc). I don’t think that the sadness is going to end simply because you admitted that you were sad. You’re going to have to address it and then address it again and again and again. There will absolutely be days and nights and weekends where you feel desperately lonely and nothing you do makes it go away. That is life. That can happen in a relationship, too. Don’t walk away from it! Face it. Sit with it. Carry it. Examine it. Ask yourself hard questions about what you’re really sad about. Whatever the right metaphor for you is—do that.

THEN when that work is “done” (it will never be done-done) you can start building your life up. This is not to say that your life is empty now by any means, but the more your add to your life and yourself the more ready you are to add someone in when the time comes (and it will come!) and the more easily you can spot people who won’t fit into your life when they come around (and they will come around!)

Please remember that dating is not a numbers game, it’s a waiting game. You can’t rush it along. You can’t meet so many people that finally one agrees to date you. I mean, I guess you can but that’s going to suck. You have to wait it out. And the only thing you control is what you do with the time while you’re waiting. This is… of course… a very bullshit thing and if I had power I would send you a hot hunky perfect partner right now!!!!! Some day you will meet someone very perfect for you and that day could be seven years from now. It might be seven years from now even if you go on a bunch of dates and are completely yourself and you do “all the right things.” Again, all you can do in the meantime is keep living a life you like as much as possible. There’s no other option, sadly. It’s not about when you least expect it or when you finally learn to love yourself. It’s just a totally random thing you have no control over.

Good luck. You’ve got this. You do not need to be happy about it or optimistic all the time. You’re allowed to complain and wallow and shit talk. You’re not meant to be perfect!

There is nothing wrong with you (but you knew that!!!!!!). There’s nothing wrong with being single and there’s certainly nothing wrong with wanting to not be single any more.


Sophia Benoit writes this very newsletter; she also writes about sex & relationships for GQ, tweets about everything else at @1followernodad, is 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 1followernodad@substack.com.