To Be Single Or Not To Be Single

Have I got a question for you. Or rather, perhaps, a rambling plea for general advice. Sorry this is long, I have been out for drinks and am confused about the whole thing anyway, hence the need for advice.

Basically, here’s the thing: I’m sort of in a non-relationship with this guy, and am having trouble figuring out whether or not that’s okay. This has been going on for a couple of years, which is way longer than I would have expected, at the outset. When I met him, I’d just ended a long relationship and wasn’t looking for anything serious. There are things about him which I find troubling: he never goes to the doctor, he sleeps on a terrible futon, he doesn’t tip well, he’s not great at communicating, he’s hard to trust or count on. He rarely invites me out with his friends, and doesn’t make a very good effort with mine.

He’s in his late 30s, if that makes any difference, and I’m in my early 30s; I know we might sound younger.

The thing is, I don’t want kids. When I think about my life and my future, I do eventually want a long-term relationship with a real partner. My family and closer friends are kind of scattered, so sometimes I wish I had someone consistent to rely on and hang out with a bit more. For now, though… I enjoy a lot of things about being single, and I don’t feel much pressure to get it all sorted out by any particular deadline.

This guy though, this is the best sex I’ve ever had, so there’s that. I have bouts of mild depression every once in a while, and he handles them well, and is supportive without taking it personally, which I don’t think I’ve encountered before. We do love each other, we have some interests in common, and have a lot of fun hanging out together, but I have real doubts about whether something serious with him would work, or would even be good for me at all. He works in my field, successfully, he has a few old, close friends who seem cool, and he’s lived with girlfriends before, but he doesn’t display a lot of reliable behavior to me, specifically.

So, I don’t know. Am I being a wiener for not asking him to get serious with me? Maybe that would make things different between us? I’m not sure. Am I trying too hard to be “cool” and not ask for too much? I’ve found in other relationships (mainly with friends and family) that it can be hard to articulate exactly what I want, but sometimes it really can be transformative. We recently had a fight and reconciliation; he re-connected with an ex (briefly), told me he was exclusive with her, and I freaked out a bit, given that I had been under the impression that he hadn’t wanted anything serious with anyone. It consumed a lot of my energy worrying about this and what to do, but now we are having lots of snuggly times, and he’s re-stated that I’m important to him, and if I want more of his time, it’s mine. And I am feeling all of these soft squishy feelings that I don’t totally trust. He’s “not sure” what he wants, from his life in general, obvs.

Is it cool to keep things casual, and just try to relax? I think I can chill out a little, though it doesn’t come that naturally to me. Alternatively, I find it very difficult to imagine walking from him. How does one do such a thing? In the past, when I’ve withdrawn a bit, he comes on strong with apologies and sweetness and attention and promises to try and do better, which I am a sucker for.

Is it misogynist nonsense to think that I can’t maintain a satisfying long-term casual thing? I feel like there’s this “The Secret”-ish idea that if I want a relationship, I should get rid of this person who’s not offering that, but I don’t really buy it — then would I just be needlessly celibate for months/years until I meet someone else? Why shouldn’t I enjoy this even if it’s not exactly what I hypothetically want? Am I being too picky? Am I thinking too much? I have, for the record, been dating other people off and on throughout this whole thing; the guy in question knows this and seems mostly comfortable with it. I like to be fairly choosy, and am wary of jumping into a new, unsuitable relationship to help break this one off.

So, question: can I have my cake and eat it too? What is happening? What should I do? I guess I am a little stuck. I feel like my friends are tired of hearing about this, and would be thrilled if I would just get rid of this jerk already. They might be right, but my own feelings won’t quite sign off on that. Can you advise?


This is a great letter, never apologize for length! How are you supposed to get at all the angles if you don’t ramble on a bit?

And there are so many angles…

I have read your letter a couple of times and this is one of those advice letters where I’m not totally sure what you’re asking. Are you asking me if it would be “settling” to try to throw in your lot with this guy who has never expressed the desire to commit to you and who you aren’t even all that into? The answer is probably yes. Are you asking me if settling is okay? Well, the answer is also pretty much yes, sometimes, although I don’t think anyone would say it was ideal. But it can be nice! Fine! If you don’t want to be single and you feel you’re getting old and you meet an okay guy you like pretty good who’s nice to you, sure, go for it, don’t feel bad. I was one of the ones who thought Mrs. Hughes should absolutely have married that random childhood friend in her old age, instead of continuing to live her dream of being a house maid (Downton Abbey reference, in case you are confused). Are you asking me if I think you should settle? This is trickier. I don’t know your life. I don’t know if settling is right for you, at this time.

With the exception of this guy, your life sounds cool. You’re a 30-something newfangled woman, who isn’t super focused on traditional womanly goals like Husband and Baby. You enjoy a lot of things about being single. You’ve got a life and a career and friends and this guy is just kind of ho-hum.

I say he’s ho-hum even though you list his merits. Lets examine:

– great sex. Great sex is not to be overlooked! It’s awesome! Sex is a big part of life, it’s a big part of what makes a relationship work. However, I am someone who’s always tooting the “sex isn’t everything” horn. I definitely think you have to have good sex with your ultimate life partner, but at the same time I don’t think good sex automatically makes someone a good life partner. For example:

– “some interests in common.” Oh girl, that is tepid praise indeed. I have “some interests in common” with almost everyone in the world, including George W. Bush (he exercises! he loves his dog!). I mean, I already think “we have common interests” is already making something sound kind of clinical, but “some” interests is even worse. You can have just “some” interests in common with your ultimate life partner if he is fucking stellar in all other realms and makes you feel like a million bucks and is devoted to you, but….that does not describe this guy.

– you have fun together. Again, important, but not enough of a plus to base a partnership on. I have fun with all my friends, but would marry very few of them and I’m sure the feeling is mutual.

– he’s nice to you when you’re depressed, in a way you haven’t encountered before. To me this is perhaps the most meaningful one! That’s probably a pretty special quality–that this guy is able to interact with you in a way you appreciate, during a time that is probably raw and weird and difficult for you. I can appreciate that this feels good, that you feel safe with this guy. But again, is “nice to me when I’m depressed” enough of a reason to decide to settle down with a dude in a boyfriend-style way, even though it doesn’t sound like you even like him that much?

I don’t know. Some interests in common, great sex, fun together, nice when you’re depressed–on paper, this sounds like an acceptable, if not brilliant, match, but I have to point out that the WAY you write these words is what’s tepid. You’re basically saying “he’s pretty good I guess, should I go for it?” Like of course no one’s going to be like “Yeah, go for it!” after hearing something like that. I kind of find that sort of question to be a bit sad. You say yourself you’re not desperate for a husband, so why are you so desperately trying to make yourself decide to try to turn this guy into a husband?

Furthermore, it doesn’t sound like he WANTS to be your husband!!!!! You have been sleeping together for YEARS, and somehow it’s never become a Thing, a romance, a partnership? AND it’s never been broken off? That’s a hard thing for me to imagine, but that’s just me, I know. Still you know what gives me pause? That after all these years, he suddenly got back together with an ex and then was just like “it’s over, you can call me if you want.” That, to me, does not sound like someone who’s going to become boyfriend/partner material anytime soon. I feel like if you guys were going to Fall In Love it would have happened by now. And now it sounds like you’re trying to talk yourself into Being In Love with him, when really he’s just your friend you happen to have incredible sex with. I should note you don’t even talk about him like he’s your “best friend.” It’s like there’s no passion whatsoever in any of your feelings about him. You seem mostly just confused about what this relationship even is. I don’t think that’s enough of a reason to try to make it into a big serious thing, just to see if that ends up being a good idea. You’ve already invested years!!!

In addition to half-heartedly laying out his praises, you also tell me his flaws. Some of them (futon, doctor) are sort of normal, although I understand you finding them troubling. But lady, “not great at communicating” and “hard to trust or count on?” “Not reliable?” This is who you want to hitch your wagon to the star of? He doesn’t care if you’re part of his friend group; he doesn’t care if he’s part of yours. There are two issues here:

1. It doesn’t sound like you want to be his girlfriend
2. It doesn’t sound like he wants to be your boyfriend

These two things together make me go: ??

I think maybe what you’re feeling is the desire for A boyfriend, even though you say you’re not super focused on that. I think in being confused about this guy who is obviously not boyfriend material, you may be revealing that you actually are feeling the desire for a boyfriend. You feel like your friends and family are scattered and you’d like somebody consistent and stable in your life. That’s obviously not this guy, but since he’s the guy you’ve currently got, part of you is trying to turn him into that. To me, this makes sense and I can totally empathize. I also don’t think it’s bad or weird to “want a boyfriend.” Partners are nice. Partners provide a safe space, a rock in the middle of this swirling river of life. Coming home to a partner is a wonderful thing. I should stress however that I mean a “GOOD” partner. An actual partner. Not a guy who sleeps with you for years and yet somehow never becomes even your boyfriend, much less a Life Partner Style Person.

OKAY but lets get to the other part of your letter, which is this question about is it just a dumb Secret-y thing to believe you need to get rid of this frankly kind of random-sounding dude you’ve been boning for years in order to find The One.

I don’t believe in The One, but I do believe in The Ones. I think there are some people out there who are going to be amazing matches for you; who make you feel good all the time; who communicate well; who you trust; who want you to be a part of their life; who think you’re incredible; who want to be devoted to you; who challenge you in exciting ways; with whom you will have great sex. I think there are probably like at least one thousand people in America you could have that with. Maybe more like 10,000, I don’t even know. I just think that in spite of the mystical alchemy that makes a Good Relationship, its nuts and bolts actually aren’t that fucking hard to figure out, if two people like each other, aren’t psychotic, and want the same thing, which is to have a nice life together.

So, is this guy one of those guys? It doesn’t sound like it, but only you can know for sure. There are probably a trillion red flags in your letter, not the least of which is the fact that all your friends wish you would just get rid of “this jerk” already. If all my friends thought the guy I was boning was a jerk and they were sick of hearing about him, I’d think something was probably not going well in that area. I can tell that you already know this.

But so, if he’s not one of The Ones, then is continuing to bone him for the entirety of your 30s and beyond, indefinitely, going to be non-conducive to actually finding one of The Ones? And in this case my gut instinct is YES.

Why? Because even though he’s Not Your Boyfriend, and even though It’s Just Casual and even though frankly it doesn’t even sound like he’s all that nice to you (friend group issues; trust issues; communication issues; getting back together with ex and unceremoniously dumping you issues), he’s still occupying the spot in your life that is the Dude I’m Boning spot. I think if you are honest with yourself you will see that you ARE dating him. You’ve been dating him for years. You are thinking about him; wondering about him; “freaking out” when he does certain things. You are writing tortured letters to internet advice columns asking what you should do about this non-relationship relationship. All this means that actually NO, you’re NOT open to the possibility of finding another dude who is perhaps better suited to you! AND, you’re not actually living the self-fulfilling single life, either–this is very clearly NOT AT ALL “just a casual thing!” How are you supposed to be “dating yourself” when you’re actually dating this guy? How are you supposed to be all fresh and happy for Mr. Right to pop by if you’re sitting at home wondering if you should try harder to make yourself want to be with Mr. Wrong enough to try to force him to want to be with you too? Jesus!

I don’t think casual sexual relationships are bad at all. I think they can be great, and fun! But if they go on for years, and if they ultimately start bumming one of the parties out (you), and making her ask all kinds of sad questions about Should I Try To Force This Into A Real Thing Because It’s Starting To Feel Weird, then I think maybe all the casual joy has been wrung out of the situation and now maybe it’s time to start a new phase of your life, one in which you are NOT not-dating this guy.

Ask yourself what you get out of it. He sounds like an okay friend, although one you don’t share other friends with. But you know, you have fun with him, he’s nice when you’re depressed. What else do you get out of it though? Don’t you have lots of friends who are fun? What are you getting out of this situation? Is it the sex? It might be time to try to find someone else to have great sex with. It sounds like this guy doesn’t provide you with any kind of Safe Space or deep emotional support in that good boyfriendy way, he obviously doesn’t make you feel that special, he doesn’t want a girlfriend because he’s in his late 30s and doesn’t know what he wants at all, like in his whole life…what exactly do you sincerely get out of boning this dude for years? Because honestly? Your letter DOESN’T SAY.

I do agree that asking for what you want–naming it–can be transformative. I guess I’m just wondering what it is you DO want. Do you know?

Maybe make a list. “What I want out of some sort of boyfriend figure.” It doesn’t seem like a whole lot of the things on that list are going to apply to this guy.

I want to stress that I’m not saying this guy is a jerk or anything. I think he’s just kind of a bum, which is fine. It sounds like he’s being honest and everything, like he actually sees your humanity and doesn’t want to hurt you. I’m sure he likes you! But is that enough of a reason to decide to try to get him to be your boyfriend? He sounds like a bum with no great ambitions in the personal development area (desire for endlessly casual sex rather than relationships; futon). I think it is a fool’s game to try to turn a wishy-washy bum into some sort of delightful stable life partner. It just doesn’t sound like who this guy is, fundamentally.

Just judging by the tone of your letter you just seem kind of exhausted with this situation and with this guy. You seem not very passionate about him. You seem ambivalent about him. You seem tired and a little disturbed by how long this has gone on and you seem a bit exasperated with yourself. This all does seem to point to some advice: Unequivocally break it off with him, ask yourself some deep questions, shake things up a bit, get a haircut, and try ACTUALLY BEING SINGLE maybe. Because right now, you aren’t single. Maybe you’ll like actually being single a lot more than you think you do! Maybe you’ll figure out more about what you want in a dude, for real, and thus be more likely to get it.

How to walk away from him? The age-old question, and yet the answer is simple. You just do it. You say “you’re a good friend and I love you, but I want something more out of my life, and I want a fresh start, and so I don’t want to have sex anymore and lets not talk for awhile. No hard feelings?” and you shake on it. Easier said than done, obviously, but still that’s basically it. And if he comes at you with apologies (? what’s he apologizing for, if you are explicitly not dating this whole time? You are clearly dating!) you say “thank you, but this isn’t personal. Please don’t call me for at least six weeks” or something. You tie a piece of string around your finger that reminds you you made this decision and you aren’t going back on it even if in the moment you want to so bad. Yes, you’ll be sad, because he’s been your boyfriend for years and there will feel like there’s a hole in your life where casual sex with him once was. But that hole is part of the process–filling it with other stuff, I mean. That’s how you grow and learn and get to a different place in your life and in your personal development. Of course it hurts, but that’s life. Breaking up with someone hurts. CHANGE hurts. Confronting stuff you don’t want to confront hurts. Addressing stuff in your life you want to be different, and then taking steps to make it different, hurts. Starting to exercise hurts. Getting that rotten tooth removed hurts. Quitting sugar hurts. Quitting smoking hurts like hell! Missing somebody who was there for a long time hurts. But none of this is reason enough to not do these things, if you know they are for the best. Giving birth to a baby fucking hurts but that’s how you get a baby! Terrible example since neither you nor I want to have children but you know what I mean? Pain is built into life; pain is part of change and growth. Like when you’re a kid and your bones are growing and they ache in the night. You can’t make an omlette without breaking some eggs, etc.

I think bottom line, you should believe that you deserve happiness and a real partner if that’s what you want. AND you deserve an actually-fun Casual Sex Relationship, if THAT’S what you want. But what you have right now is neither, and that sounds like it sucks.

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2 Responses to To Be Single Or Not To Be Single

  1. Toby Milliken says:

    Have some dignity. You’ll do great. Break up with him and make friends with your hole. You can do it!!!

  2. dv says:

    This advice was perfect!

    Also, I find it really curious that so many people who write in to advice columns are having “the best sex ever.” It’s just odd because it’s a very common theme.

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