DEAR DR. NERDLOVE: I’m in a small-to-medium sized social group of friends that started off as a sort of school-based gaming guild. We all got together over (virtually) over the pandemic as a way of keeping each other company by playing MMOs and virtual tabletop games together. Once we started getting vaccinated and the lockdowns eased, we started hanging out in person too.

Over the months, I got pretty close with people and if we’re not all good friends, we’re at least acquaintances who can say ‘hi’ and grab a quick lunch together or something. And of course (because why else would I be writing?) I started to get feelings for one of the girls in our group.

I’m fairly certain she doesn’t know. We’ve hung out on our own a few times and with other friends before I started feeling attracted to her and I think we were on track to being friends before I started wanting more. I think I’ve kept my feelings to myself pretty well, and I haven’t said anything because I don’t want to screw things up. What makes me nervous is how many of the other guys and girls in the group have talked about how dating friends makes things awkward or how people falling for each other ruined other groups. I don’t want to have that happen to me and I don’t want to ruin things for everyone else.

Is there some way I can ask her out? Should I be letting this go because it’ll just mess up the guild? Is it bad to ask someone out when you’ve been friends for over a year and is she going to think I was just pretending to be her friend?

Help! I don’t know what to do.

Secret Friend Destroyer

DEAR SECRET FRIEND DESTROYER: Y’know, SFD, I hear about “I’m afraid to ask someone out but I’m afraid it’ll ruin things” fairly often. What I don’t hear is how, exactly, this great calamity is supposed to happen or why. Is it the fear that the couple will eventually break up and everyone will be “forced” to choose sides? Is it because two people dating would somehow change the vibe and so everyone has to stay strictly platonic? Or maybe because one person had a crush on someone else, but they started dating another person and the dude (or dudette) who got left out made it everyone’s problem?

I dunno; it’s a lot like the Loch Ness Monster: everyone talks about it, but very few people have actually seen it and the ones who say they have have usually seen something else entirely.

That being said: in my experience, the reality isn’t that being attracted to somebody or even asking them out – successfully or otherwise – actually changes things or makes things awkward. What usually makes things awkward or uncomfortable is when one person or another is an asshole about it. This came about in some fairly common, universal even, scenarios.

You had the guy or girl who couldn’t take “no, thank you” for an answer and would make their entire friendship about “but whyyyyyyyyy won’t you date me?” You had the prototypical Nice Guy who was only in the group/being their friend in order to get into his crush’s pants. There’s the “we had sex once and now everyone knows about it because someone couldn’t keep their mouth shut” scenario and the “takes every opportunity to try to force their crush to interact with them via the game” guy, topped only by “the guy who turned everything sexual with the other person, no matter how inappropriate, in game or out of it.” And of course the classic “my crush is dating someone else and I’m going to throw a fit about it every chance I get.”

In short: assholes who couldn’t be bothered to act like a person. When the individual acted with courtesy and respect, there was rarely any actual awkwardness or “ruining” the group. The same goes with two members of the group hooking up or starting a relationship. People almost always took it in stride and there was rarely any real awkwardness…  and I only say “rarely” because of the aforementioned “my thwarted crush is everyone’s problem now” situation.

Even break ups weren’t automatically friend-group destroyers. Any drama fallout from the break up had less to do with some sort of “dating within the group is bad” and much more with “people handled the break up badly,” that ultimately only served to highlight fractures and fissures that were already there. In those cases, the group was always going to come to a dramatic end; it was just a matter of who was actually going to trigger the meltdown.

Now I can understand why you might worry. If you were to ask your crush out in a way that made them uncomfortable or gave them reason to feel weird about having you in the group, yeah, that’s going to be a problem. But it sounds like the two of you have a fairly good platonic relationship already, especially if you’re already hanging out as buds. If you were to say “hey, I really enjoy hanging out with you, but I’d be interested in taking you on an actual date. Would you like to go do $COOL_THING at $FUTURE_TIME?”, that’s hardly going to blow people’s minds or send them screaming from the room. Similarly, if she were to say “no, thanks” or “I’d rather just be friends”, and you respond with “Ok, no problem, thought I’d take a chance,” and continue to be her friend? Yeah, you should be just fine.

The one thing I could see being an actual worry is any initial awkwardness – either after being turned down or in the event of the relationship ending in a non-earthquakes-birds-and-snakes-and-aeroplanes scenario. In both cases, the way you handle it is… well, to power through the awkward together. And one of the best ways to do that? You call out the awkward. Part of what makes the awkward so uncomfortable is that nobody is willing to acknowledge it. It’s hanging there, unmistakable as a fart in church and yet nobody’s willing to say anything. Well, someone’s got to call it out, so it may as well be you.

In those situations, you want to say – literally say out loud – “so… this is a  bit awkward, huh?” This is your magic phrase to deflate the tension in the room; in fact the most common response tends to be “OH THANK GOD SOMEONE SAID IT”. The fact that you can acknowledge the awkward is a sign that you’re willing to actually handle this like a grown-ass adult instead of pretending that it never happened while everyone else gets increasingly uncomfortable. If you can call out the awkward, you are signaling that you’re ready and able to talk about what happened and move forward with being friends.

(Of course, this gets taken right back if you now make every conversation about how you two didn’t get together and hey why didn’t it happen, again? But that comes right back to “take no thank you with good grace”.)

As the saying goes: actions have consequences; if you want the consequences, you better take action. So my advice? If you’re feeling it, ask your crush out on a date. Not “hang out some time” like you’ve been doing, not some ambiguous “maybe a date, maybe not, I’ll decide when the night ends.” weirdness, but an actual, directly stated date. If she says yes, hey, blessings on you both. If she says no? You say “Ok, thought I’d ask,” and then treat her exactly as you did before, continuing to be the cool guy and good friend you were before you asked her out. People will look to how you behave for clues for how they should respond. If you don’t start drama, there won’t be drama.

And if other folks have a problem with the two of you getting together or think that dating within the social group should be forbidden… well that’s a them problem, not a you problem. Dating’s not a democracy; other folks can have opinions, but they don’t get a vote or a veto.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE:

This is how my mind works when I see an attractive woman I want to talk to:

“Hey, my coworker is pretty cute. I wish I could get to know her more.”

“She’s in a different department, how could I talk to her?”

“If I were to go up to her for no other reason, that might creep her out.”

“Creeping out a coworker would be disastrous. What would that even mean for me in this job?”

“Do I even know how to start a conversation with a woman without creeping her out?”

“How would I even find out how to do that? Just keep approaching, trial and error, creeping women out until I eventually find out how?”

“I can’t even learn how to do that without creeping out women…”

“How can I even date without that knowledge…”

“What woman would want to date such a sad sack like me…”

And then I go into an anxiety and depressive spiral for the next few days, sometimes weeks. You can replace “coworker” there with “acquaintance”, “woman in my dance class”, or “woman at the bar”, and it’s mostly the same.

So what do I even do?

My Own Worst Enemy

DEAR MY OWN WORST ENEMY: I get variations of this question all the time and it’s almost always about hypothetical situations; it’s never about times when those incredibly harsh rejections have ever actually come to pass. In fact, outside of friend-of-a-friend stories tossed around in comments sections, I have yet to actually hear from anyone who’s actually had any of these things happen.

(Of course, the few times I see “well, I asked out a woman at work and then she maced me and called the police and I lost my job,” get tossed around by JohnnyBunchONumbers on Twitter or Reddit, they’re always surprisingly sparse on exact details — literally all you did was say “hey, would you like to get coffee on Thursday” and you lost your job over that? Those exact words and nothing else, no other information or prior history? Ok Chachi, care to show me the HR write-up of the incident that would confirm this?)

Now the fact that these are all hypotheticals, as your brain-weasels toss out any number of worst-case scenarios, each more dire than the rest, doesn’t mean that they aren’t upsetting or demoralizing. But they are just that: hypotheticals, based on nothing but your own anxieties and the crabs-in-a-bucket moaning of folks who want to believe that hope doesn’t exist. They’re intrusive thoughts that nag at you because they play to your worst fears. So I sympathize. I really do. I’ve been there, I’ve done that and built a literal career out of trying to stop having those thoughts and anxieties.

And hey, maybe you, like me, are neuroatypical; finding out that rejection-sensitive dysphoria is a common comorbidity with ADHD was a revelation to me, and getting treatment made a huge, huge difference. Or, alternately, you had a really bad experience when you were younger and it left its scars on you and your soul. This is also a thing that happens, and its entirely understandable that this fear would linger. “Once bitten, twice shy” is a cliche for a reason, especially if it happened to you in your tween or teen years, when your brain is still developing and things like “rational thinking” are more a theoretical concept than a reality. The crap that hits us when our brains are in full Hormonal Chaos Overload tends to seem larger, more real and more universal, in no small part because we have neither the bandwidth nor the experience or perspective to recognize that this is the exception not the rule.

(This is, incidentally, why I insist that dating in high-school shouldn’t be a priority. High-school is basically medium-security prison for kids, and treating it like any sort of realistic model for the rest of your life is a mistake of the first order.)

Just as importantly: it’s worth remembering that our brains don’t distinguish between what we imagine and what we remember. When we imagine these awful outcomes, our brains treat them as things that actually happened. In a very real sense, when we linger on these imagined scenarios, we are hurting our own feelings.

But by that same token, if what we imagine is functionally indistinguishable from memory… why not change the script? Why not, instead, choose to imagine things that actually benefit us, instead of bullying ourselves mercilessly? After all, if we’re going to deal with confirmation bias, doesn’t it make more sense to choose the beliefs that actually help, instead of harm us?

Yeah, I can understand why this might seem absurd. But if what your jerkbrain is whispering into your hear are hypotheticals anyway, why not try changing things around for yourself?

Here’s how you start the process, MOWE. When you start to have these thoughts, ask yourself this question: “why?” “Why would they be repulsed by me?” “Why would my just talking to someone creep them out?” And, most importantly: “why do I believe these women are so shallow, so cruel or so without compassion that my talking to her like a person would cause so many problems?”

This last one’s important, because it really gets right down to the core issue: there’s some part of you that doesn’t just worry that there’s something unloveable about you, but also believes that women aren’t going to actually, y’know, understand. Yeah, we’ve all seen the “ugh, why are men??” posts on subreddits or TikTok or Twitter, but those aren’t talking about day to day, normal interactions. Those are understandably frustrated people complaining about assholes who can’t be bothered to talk to folks like a person or not treat women like a vending machine that you pump enough coins into and sex comes out. If you caught me after a long day of dealing with asshats who can’t tolerate someone wearing a mask around them despite still being in a pandemic, you’d be hearing me complain about people at length too. That doesn’t mean everyone I encountered that day was a COVID-denying s--thead; it just means I’m venting.

Instead, consider this: much of what you’re worried about – coming off weird, saying the wrong thing, being misunderstood – are all things women experience too. Despite how often people insist that dating for women is like hailing a taxi (“she just has to raise her hand and a dozen show up”), women experience the same nerves, the same fears and have made the same embarrassing gaffs, blunders and f--k-ups. There is not a woman on this earth who hasn’t had a moment where she’s shoved her foot so far into her mouth that she’s still burping vulcanized rubber. So, even if you were to say something incredibly stupid or awkward, not only are most folks going to understand, but most folks probably won’t even notice. I know it feels like you’ve got a spotlight shining directly on you, but I can promise you: we’re all so caught up in our own drama that a verbal flub or whatnot isn’t going to even register on the top 20 events that happened to her that day.

As you ask yourself those questions – and remember that women have the same fears and the same anxieties you do – the next thing to do is to change the story you’re telling yourself. Consciously choose to set those negative, intrusive thoughts aside and gently direct your mind towards imagining a positive outcome. Picture the scene in your head: you go talk to them and… nothing bad happens! Everything goes well! Imagine the scenario where you have a pleasant conversation and everyone feels better for having had a lovely experience. Picture, in as vivid tones as you can manage, that the person you want to talk to thinks you’re charming and delightful and gives you her number before you go. Do this every time you have these thoughts; make a habit out of it, and you’ll be surprised how much it becomes your new default.

And one more thing: I’ve approached more strangers than you’ve had hot meals. I can tell you, from personal experience, that the worst outcomes are “they ignore you”. They turn their backs, they don’t respond or otherwise act like they didn’t hear you. No “how dare you talk to me”, no harsh rejections, just distantly polite or nothing at all. And I’ve had moments where I have actively made mistakes – tripped over my own tongue, said the wrong thing in a moment of panic or, in one memorable event, literally choked. As in: I tried to talk to someone and aspirated on my own saliva.

9 times out of 10, they never noticed or cared, and the 1 time out of 10 they did notice, I was able to recover and move on from there; my weird faceplant would just end up being something we’d laugh about together later on.

This is your jerkbrain screwing with you, MOWE. You can take control back and change the narrative.

All will be well.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

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

DEAR 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 f--k??

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.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com