How Can I Help My Hopelessly Single Friend Find Love?

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How Can I Help My Hopelessly Single Friend Find Love?

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Dear Dr. NerdLove:

I have known my best friend (40/m) for most of my life. He and his family have stepped up and supported me through so many difficult times; he is my daughter’s godfather and helped me raise her when I was a single parent. We live in a communal house, and just bought a new property in a rural community. 

He is a wonderful person, but since we have moved, he has taken to wistfully talking about wanting a serious relationship. This often comes in the form of comments about how his future wife is missing from various situations. But occasionally, it is him objectifying random women. It makes me so uncomfortable, and angry when it is in front of my daughter, that I don’t really know how to react in the moment without word vomiting the abridged contents of a gender studies course at him. He wants biological children, and has an aversion to dating divorcees.

I feel bad for him, but I am also exhausted listening to him go on about it. I don’t even know how to help him, because he puts in no effort to meet people or leave the house. He was too shy to introduce himself to the sweet old lady next door, when her mail was accidentally delivered to our house. He thrust the envelope at her and fled back to our house. He has been pressuring me to go out and meet people and then bring them back home to meet him. Unless I happen to make friends at the library, this is a near zero possibility.

We are all introverts. Everyone plays board games and video games together. This man has played World of Warcraft religiously for longer than kiddo has been alive and has never made an in game friend that I didn’t introduce him to. When we go to social events, like conventions, video game tournaments, and movies, he won’t talk to anyone outside of people we know. He has a good (all men) friends group that he socializes with weekly online, and that’s it outside of the house.

I worry about him even inviting a woman home, though. In our computer room, his desk is a nasty gamer hole. Kiddo gags when she looks at his keyboard. His room is no better. I am afraid to witness him attempting to take a woman up to his floor mattress bed, or her horror when she realizes he has never used his toothbrush. The secondhand embarrassment would be awful.

I don’t know how to tactfully say, “Hey bestie, this comes from a place of love, but clean your room and brush your teeth. AND I can’t find the love of your life for you. Just talk to people when we go out, without commenting on their bodies like a total creep.” I don’t think I can handle him going on about his imaginary future wife much longer.

Switch To Hitch

Oof. I feel for you STH; it can be really frustrating to hear a good friend lament his eminently fixable misfortunes, especially when he won’t lift a finger to actually do anything about them.

That’s ultimately the issue here, though: the solution to all of this requires change, and he doesn’t want to.

This is actually a common self-imposed limitation, especially among men: they want a girlfriend, but they don’t want to make space for a girlfriend in their lives. They want a woman that they can slot effortlessly into what they already do, but they don’t actually think about what having a girlfriend would entail. It’s more as though they like the idea of looking over and seeing someone pretty while they do their usual thing, but not someone who would actually have needs or desires or wants of their own.

Don’t get me wrong; this isn’t to bag on dudes who think this way. I mention this because most of the guys who are like this haven’t really thought about what going and trying to find a partner would entail, nor what it would mean for their day to day lives. They have an idealized version of what they think they want, but haven’t really thought it through.

This is in no small part why so many geeky men will fetishize geek women; not only does it mean that they don’t need to confront their feelings about their own interests and identity, but it props up the fantasy that they could just slot a woman into their lives with minimal change and friction. “Of course she would want to do all the things I already do,” the thinking goes, “that’s what would make this the perfect relationship!”

Unfortunately, the reality of geeky women is that while yes, they may have similar habits or hobbies… they’re still people and it’s still a relationship.

You can’t treat a relationship like a cactus, where you water it occasionally when you remember but otherwise let it fend for itself. Relationships require active participation from both parties, and without that active participation, it will fall apart. But a lot of guys, especially guys with relatively little relationship experience, realize this at first. At the risk of an uncomfortable metaphor: in some ways it’s like someone who gets a pet without realizing the amount of effort involved in the care and feeding of it. It’s not that they’re bad people so much as they didn’t think and what they were expecting was furniture that breathes, rather than a living, thinking being that requires their active participation.

(And because irony, not gravity, is the strongest force in the universe, my cat just knocked my pen off my desk in order to get me to throw his toy for him.)

This is, at the core, the biggest issue your friend is dealing with; he wants the idea of something, but hasn’t thought about the reality of what it would mean. If he legitimately wants a relationship – a real relationship, not just the human equivalent of breathing furniture – it’s going to entail making space for that relationship in his life. He’s going to have to confront that he’d have to make substantive changes – not just to his living conditions and behavior (and also: he’s never used his toothbrush!??!) but also how much it would change his lifestyle. He’s going to need to actually, y’know, go out and do things outside the house – whether going on dates or just the basic day-to-day minutia that come with having a partner, especially a partner you live with.

As I’m often saying: if you want different results, you have to do things differently. Until he’s ready to accept this, take it on board and actually make changes, that’s not gonna happen.

Now, here’s the problem you have: you can’t make these choices for him. Nor can you make him choose to act differently or make him take the actions he needs to take, and you certainly can’t (and shouldn’t) do those things for him. You can encourage him, sure. You can point out the folly of his predicament. You can even point out, in great detail, just how much his lack of hygiene, grooming and basic cleanliness is holding him back. But unless and until he decides for himself that he’s ready to make changes, nothing’s going to happen. And, straight talk: you can’t push him into doing any of this, and quite honestly, it’s not your responsibility to do so.

Don’t get me wrong: I absolutely understand the frustration. I can understand the impulse to want to grab him by the scruff of his neck and shake him until some motivation rattles loose. But, even if you could just control him like a marionette and force him to clean his room or drag him in front of folks, all this will do is either breed resentment for you and guarantee that he’ll half-ass it all at best and then complain even more. But at the end of the day, it’s ultimately his life, his choices and his responsibility.

With that being said, I don’t want to leave you with “welp, sucks to be him byeeeeee”, so let’s talk about what is within your power to affect here. To start with, you can provide incentive to change his act… and take care of yourself and your daughter in the process. This will entail setting some pretty firm boundaries with him, especially about his constant stream of commentary about his imaginary future wife or his objectifying women. You need to lay down a firm line here: “I don’t want you talking like that in front of me or my daughter,” or “I’m not interested in hearing about your imaginary relationship when you’re not willing to do anything about it.”

In both examples here, you’re making it clear: there’re things you’re not going to accept from him, period. You don’t need to teach him about feminist theory, the male gaze or otherwise educate him as to why what he’s doing is problematic or detrimental to his chances; that’s not the point of laying down those boundaries. The only thing he needs to know is that you don’t find this behavior acceptable and if he wants to engage in it, he can do so when he’s not around you. But if he wants you around, then he’s going to have to accept that his actions will have consequences; being a grown-ass adult means accepting the responsibility for your choices.

The same, incidentally, goes for teaching him why his comments are bothersome. If he genuinely wants to learn – as opposed to just offloading the responsibility onto you – then he’s going to have to make the effort himself, instead of having it spoonfed to him by the person who laid down the boundary. A lot of folks will often use “but why?” and “but how will I learn if you don’t teach me?” as ways to push back when folks lay down a boundary about their behavior. And to be clear: that isn’t about being predatory or trying to test people’s boundaries, it’s a reaction to having lived in a culture that’s put incredibly few restrictions on male behavior and then suddenly encountering them.

In a lot of cases, this can be reflexive, rather than a conscious effort to control or manipulate folks. A truer measure of the person’s character in this case isn’t their initial or reflexive reaction, but their next reaction. Are they willing to accept that you’re allowed to set a boundary where you choose, without explanation, even if they don’t necessarily understand? That’s good. If they continue to demand explanations or that you teach them why, then what they’re saying is “I will only respect your boundary if I agree to it, therefor it’s your job to make me agree.”

So that’s the first step. While this won’t necessarily motivate him to change his ways, it does provide incentive to change (he doesn’t piss you off) and discourages the sort of behavior that ultimately contributes to his learned helplessness.

The next step is to recognize that while you can’t make his decisions for him, you can provide motivation and assistance… if, and only if he asks for help and he’s willing to listen. Much like drawing a line and saying “I don’t want you making those comments around me or my daughter”, you tell him “if you want my help, then you need to ask for it specifically, you need to listen and you need to actually do the work yourself.” Odds are, if he’s actually serious about wanting a relationship, he’ll at least start asking for help. This is where you have to tell him that he’s going to have to be willing to hear things he’s not gonna like hearing. It’s not just going to be “ok, so you need to clean your room”, it’s explaining what you told me: that even if he somehow brought a woman home, the moment she sees his room, she’s going to run screaming into the night. Or the fact that no woman’s going to want to date a guy who doesn’t brush his goddamn teeth what the actual fuck??

I mean, yes, you could act like a surrogate mom and say “clean your room and brush your teeth”, but the issue isn’t just living like a slob and needing a maid. The issue is that he chooses to live like this, finds it acceptable and doesn’t recognize that this is part of what’s going to hold him back. This is very much a case of “change needs to come from within”. If he doesn’t internalize that he needs a certain level of basic hygiene, grooming and cleanliness, any changes you push him into will vanish into a puff of Cheeto dust the moment you stop applying pressure.

Incidentally, getting him to explain his rationale is often a surprisingly effective way to get him to recognize how little he’s thought things through. This can often lead to breakthroughs, where he realizes that things need to be different. Case in point: you can ask him to explain not just why he’s averse to divorcees (especially if he’s going to be trying to date women who’re age appropriate to him) or wanting biological children, but how he plans to work around certain realities. A lot of folks who’re single in their 30s and 40s were married in their 20s. The older one gets – and the older the people you date are – the greater the odds that they’ve been married before. That’s not a judgement on anyone, it’s just demographics. Same with having biological kids: while being in your 40s doesn’t preclude having kids, it does mean there’re additional challenges. And unless he’s hoping to date 2o-somethings, those are challenges he’s going to have to be willing to face.

(Not the least of which being: dude, try to imagine having to get up every couple of hours at your current age. Speaking for myself: the older I’ve gotten, the firmer I’ve become that anything that wakes me up better be on goddamn fire or it will be…)

And if he is going to try to date 20-somethings… well, that’s going to be it’s own challenge, for a guy who doesn’t leave the house or talk to folks. But this actually is relevant to asking him to explain things and provides another opportunity for him to really think about what his expectations are. You might want, for example, to ask him to explain his idea of just how a relationship’s going to work and what would change if he were in a relationship with someone. Why would someone want to date him if his lifestyle stayed exactly the same as it is right now? What would he expect his relationship to be like? What incentive would someone have to participate in that with him?

This would, among other things, hopefully lead to his recognizing that maybe he’s going to need to do more than just do raids with his WOW guild and hope that his girlfriend’s into it or willing to hang around until he’s available again.

The more you can get him to think about what he wants, the more likely you’ll be able to help him recognize what changes he’d need to make. And while you can’t make those changes for him, you can certainly support them and help facilitate him finding new opportunities. But again: I say “help” not “do the work he’s not willing to do.”

The same goes for encouraging him to go out and to talk to folks. You’re not going to be bringing women back for him – not your job, and definitely not your forte. Even if you were to bring them to him, are you also supposed to do all the charming and flirting for him? He’s got to do more than hope that it comes to him and he doesn’t need to do more than agree that yes, she’s his girlfriend now. You can offer to be his wingwoman and moral support, to bring him to places where he could meet women or even push him into talking to folks… but he’s gotta do the real work.

But again: this all is contingent on his recognizing that he needs to put the effort in and he needs to choose to make changes. And yes, as the sage said: if you choose not to decide, you still have made a choice. He’s made a series of choices that’ve brought him to where he is today. If he wants things to be different, he’s going to have to make new and different choices. But until he makes those choices for himself – and it sounds like it’s going to involve a lot of choices and a lot of work – he’s going to be stuck where he is. So either he can accept that he doesn’t want to do the work that he needs in order to meet his theoretical future wife… or he can accept his life as it currently stands.

Good luck.

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