DEAR DR. NERDLOVE: I’ve spent the last decade trying to fix my life, and even though I’ve made some genuinely incredible progress, I still feel as if I’m failing at the basics.

Let me start with the positives, so I’m not just beating myself up. I used to be an extremely anxious, depressed, and socially unconfident young man. Eventually, I pushed myself hard to get out into the world. I tried new activities, went to events, met countless people, and over the years I basically became the opposite of who I used to be – confident, socially outgoing, and maybe even too independent. My physical health and finances are in a good place and still improving. I don’t live in the ideal location for socialising, but I have the time and money to go out, so I attend multiple weekly classes and go to social nights a few times a month. I’m definitely a familiar face.

Here’s the sticking point – I have never found “my people”. I’ve had acquaintances and drifted through a few friend groups, but I’ve never fit in, or I’ve made poor choices in terms of who I chose to associate with. I spent most of my twenties on Reddit and self-help sites asking, “What is wrong with me?”, and people would suggest volunteering, or going to bars, or joining a sport. I did all of it. Yet I still walked away without any real, lasting connection. I actually got banned off one site after several years for “trolling”. Out of the entire decade, I’ve stayed in touch with only two people from my studies. They’re nice, they’re good people, but we’re not emotionally close, and I rarely see or hear from them.

It would be easy to assume I must be doing something socially unacceptable to end up this isolated, but what confuses me most is that people seem to think I have my life together. I’m an attractive and social guy, so it’s always assumed that I have a lot of friends, a girlfriend, or that I date regularly. I get complimented on my appearance and personality all the time.

As for women, I get on with them fine platonically, and I know they enjoy talking to me, but I can’t seem to cross that line. When I try to get to know someone better, by suggesting we do something or even just exchange contact details, they’re simply not interested. No numbers, no dates. I’ve never been on one.

Have I tried being proactive and open? Absolutely. I’ve told people I don’t have much of a social life. I’ve invited them to do things. Either nothing comes of it, or I get the usual “too busy” or “maybe.” And no one…not one person…initiates anything with me. No one reaches out, invites me anywhere, or includes me in group chats, even though I know they have them and they’re sharing memes with each other on Instagram. I’m not hard to find.

I want to offer an example. There’s a social night I go to that’s mostly women, though there are plenty of men too. I’m a familiar face, I talk to everyone, and I even invited a couple of classmates to come along, which they did. I had people introduce me to their friends, and we all have a laugh. I got talking to a couple of new people. On paper, it’s exactly how a good social night should go. But anyone my age, especially the women, don’t really interact with me. They form their own little groups, and I end up mostly chatting with people at totally different life stages. To add to the perception issue, at the next class a guy asked how my night went, giving me this knowing smirk, because he’d seen me talking to a woman when he left. He clearly assumed we’d gone home together…but she’s married with two kids.

By way of another example, I went to a class the other day and, at this particular place, I do occasionally do some casual work and help those that are new to the hobby. One of the newcomers commented that I was a “great teacher” who made the night really fun, and one of the regulars turned around to agree, and said I was a “lovely guy”.

So I’m in this position where I am a lone wolf, trying to find his pack, and unable to make any sort of lasting connection. I’m unable to date because prospective partners aren’t interested in me, and meeting one is much harder without a social life, but I can’t form a social life beyond “Go here, talk to people, go home alone”.

I take responsibility for my patterns, and I know something’s going on, but I genuinely don’t know how to break out of it. I’ve spent most of this year crying, either alone or with my therapist, and while I’d like to believe that means I’m healing (because let’s face it, we all have things to work on), the truth is that friendships and romantic connections still feel almost impossible for me.

Looking For Group

DEAR LOOKING FOR GROUP: If you’re a regular reader, you may be familiar with the times I’ve said “there’re some crucial details missing here” with regard to people’s letters. Sometimes this is a tacit admission that there’s only so much that’s within the remit of an advice column; after all, I can’t know what you may or may not be doing wrong if I’m not following you around like it’s a reality show or an Attenborough-esque nature documentary.

(Sidebar: Hey producers, I am absolutely willing to do this. Call me!) 

Other times… well, other times, there’re things alluded to in the letter that are likely relevant to the situation but were otherwise left out.

This is a case of both. As I said: without following you around for weeks or months, it’s going to be hard to say what the precise nature of the problem is. I don’t know, for example, how many times you’ve talked with people at the events you attend, for how long or under what context before you invite them to events or try to make plans. Similarly, I don’t know – and you don’t say – whether these are one-time invitations and never to be asked again, or if you’ve made multiple overtures to the same people before giving up. However, there’re things you mention that seem like they’d be relevant – why you were kicked off a site for trolling. Which site, why they thought you were trolling… it may not necessarily paint a pretty picture or be a moment that you’re proud of, but it is relevant information. After all, we’re not different people online and off; nobody’s a completely different person just because they’re sitting behind a keyboard. It speaks to how your frustration may be manifesting in your daily life and how it could be interfering in your desire to make new friends or find dates.

Now, there’re a number of reasons why folks struggle to make connections when they’re doing “everything right”. Many times, it tends to be a matter of time and repetition. One of the issues people tend to run into is one of expectation; they expect the connections to come much faster than is reasonable. While it’s true that sometimes folks will find a crew with whom they click immediately, more often than not, it takes a while to build up the level of familiarity and connection that leads to becoming more than just acquaintances. Even in my own life, I remember multiple times as an adult where I would have to build a new social circle, and how it took some weeks and months before my friends and I had the sort of ties that meant we would get together outside of, say, classes we shared or the drawing club we were part of.

This is part of why it’s easier to make friends when you’re in school; you see the same people on a daily or weekly basis and tend to have at least weak ties to many people that could be used as a foundation for building stronger ones. The same with why we tend to make friends at work or church, or through various organizations from interest groups to even old-fashioned fraternal orders like The Elks. It can take time to build up the sort of connection that leads to “yes, I would like to hang out with you elsewhere.”

Another common factor is the “tried it once and gave up” issue. A lot of folks will ask someone to hang out or invite people to make plans, then after receiving a no or a non-committal reply, never try again. Often, this coincides with being a relative newcomer or early in class, before any real ties have been made. And while it’s understandable that you might not want to feel like a pest or risk being rejected multiple times… the fact of the matter is that sometimes you have to be willing to persevere in the face of a “no, thanks”.

The worry about coming across as needy, lonely or, worse, creepy is understandable, the same as with trying to ask someone on a date. But there’s a distinct difference between not accepting a rejection and the belief that you get one shot and one shot only. As in dating, sometimes the issue is that the person or people don’t know you well enough, you haven’t put in time for them to feel comfortable or ready to say yes, or even a simple matter of the timing not being right. If you were pestering people on a daily or weekly basis like a yappy dog demanding to know “what’re we doing today Spike huh huh huh huh?” or a sleazy guy who thinks “not if you were the last man on earth” is something that only applies to other people, that would be one thing. But if you made one overture of “hey, want to go catch the game on Saturday?” and “I don’t know about you but I could use a drink after work; wanna come?” two weeks later, that’s not going to come off as intrusive, weird or not taking the hint.

There’s also sometimes an issue of not establishing the common ground that would lead to an organic-feeling invitation. One of the benefits of sports fandom, for example, is that it’s an instant bonding topic; being able to go over the highlights and low lights and bad calls of last night’s game means that you and the other person or people have a clear interest in common. It’s a lot easier, once you’ve established that you’re both fans of the same team or athlete to extend that invitation to watch the game or even host a watch party. The same could apply to talking about food or cooking, art – anything helps show that you have this particular interest in common. Establishing that shared interest makes it much simpler to invite someone to enjoy it with you – or for them to invite you.

Still other times, it’s a matter of hosting or arranging something that doesn’t feel like it’s asking a lot or feeling too presumptuous or intimate. If you happen to be throwing a cookout with friends, inviting classmates or fellow club members you talk to feels completely normal and natural. If anything, it can be a little easier to say yes to, simply because it doesn’t presume or infer a level of friendship or connection that isn’t there yet. A group event, especially if there’re other people invited and coming, can feel like something that’s easier to say “sure!” to, if only because the presence of other people will mean that you’re not going to feel like you’re going to be stuck making awkward small talk with the person who invited you until you can make your excuses and dip.

And of course, there’s always the possibility that the way you’re presenting yourself to others is coming off in ways that may put them on edge. Or you may simply have not met folks that you are compatible with �– whether in interests or personality.

Now, it can be difficult to spot precisely where the sticking points are, especially when you’re trying to analyze your own situation. It’s very easy to let your own wants, needs, expectations and blind spots distort things. So one thing I always recommend people who are having consistent social problems is to start journaling – by hand, rather than typing or voice to text. In these cases, I recommend writing down everything about the event as factually and with as little editorializing as you can – what you said, who you talked to, what they said, how you felt when you talked to them, what happened and so on. Try your best to keep any analysis or assumptions about what other people were saying, thinking or doing to a minimum, but otherwise let it flow as directly from brain to pen to paper as possible. Write it down, then let it be; don’t touch the journal until you write the next day’s events down.

Then, every week or two weeks, pick a day and go read back through the entries from the beginning until the present and see what leaps out at you. Often, you’ll start to see recurring issues or patterns that you weren’t aware of at the time. By letting yourself write with as little conscious planning or thinking as possible, and then going back and reading it later, you help minimize letting your expectations and prejudices color what you write. You didn’t have the perspective or detachment to see them in the moment, but with the benefit of time and distance, it’s easier to spot them. Even things you thought you were aware of at the time – patterns you swear you were paying great attention to – will likely have details that you missed or correlations that you never picked up on until now.

To be sure: you have to be willing to be as factual and neutral as you can – as though you were a dispassionate and objective observer. This is hard, because we see the world through the filter of our beliefs and expectations. When you expect rejection and being disliked, you’re going to see it everywhere. But if you can focus on presenting just the facts as an outside observer might have seen them, with as few of the editorial assumptions as possible, you can start to see patterns and points where things start to shift.

Once you’re aware of these moments, you can then start to plan how to deal with them. It may be that you are stressing yourself out and ejecting early. You may never get beyond very basic small-talk – not even to talking about the latest movies or what you’ve been watching on streaming. Or there may be some clue that points to something about your behavior or mindset that’s throwing things off.

It’s tricky, and it requires a level of honesty that can be uncomfortable… and that can include positive honesty, not just “here’s all the ways I suck”. You may well realize that the issue isn’t that people like you, but that you are expecting rejection or disinterest and so mistaking “I can’t because I have a legitimate scheduling conflict” for “I don’t want to because I don’t like you”. But if you are willing to take that step back and spend the time to record and go through as much data as you reasonably can, you can make a significant head start into seeing past the filters of your confirmation biases and start to see where you’re failing to connect with your potential friends and dates.

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: Over the years, I’ve cultivated a physique, lifestyle, and sense of charisma that have opened many doors for me. I used to focus heavily on getting matches or likes on dating apps, believing those numbers defined my value. But as time went on, I realized that simply being myself — showing up with my presence, energy, and confidence — brought me far more success with women than any swipe ever did. I’ve connected with fascinating, beautiful women in real life, and those experiences have been meaningful and validating in ways dating apps never were.

This brings me to my question: why was I so fixated on Tinder matches in the first place? Looking back, it didn’t set any real limits for me; instead, it made me feel terrible about myself. And I wonder why so many younger men put themselves through this cycle of comparison and rejection. It feels like there must be an epidemic of low self-esteem fueled by these platforms — not caused by women, but by the design of the apps themselves. Yet many men end up directing their frustration and anger toward the easiest target rather than the system that’s actually harming them.

I’d love to hear your thoughts on this dynamic. Why do so many young men fall into this trap, and what can be done to break free from it?

Thank you for your time and for the work you do.

Sincerely,

Me myself and I

DEAR ME, MYSELF AND I: Oh this one’s easy, MMI: it’s a numbers game.

No, seriously. It’s numbers all the way down.

In the Before Times, the Long Long Ago, when dating apps were branching out beyond Spring Street Personals and online dating was something you were vaguely ashamed to admit to be doing, the numbers were about how many sexy singles you (the generic “you”) could potentially meet in your pajamas, compared to how many you could meet out at bars or at the park or the company mixer.   

What they were doing in your pajamas I’ll never know.

The vague shame of “having” to use the apps tended to be outweighed by the fact that it was possible to message more people and set up more dates in the span of an hour than you could in an entire weekend. It had the benefit of ensuring that you knew everyone you encountered were single and ready to Christian Mingle, and if you were a little shy or anxious about talking to someone in person, you had the benefit of text. You didn’t have to have to be a silver-tongued graduate of the Lando Calrissian School For Players, you could let your fingers do the talking and have enough time to think of what you would say next instead of blue-screening in front of someone.

That all changed when the Tinder Nation invaded. Tinder’s jab-jab-hook combo of showing matches by proximity, swiping mechanic and open “we’re all just here to f--k, right?” attitude swept over the public like smallpox and changed the game. It was the first time you would click a button on your phone and see people you would swear would never be on a dating app, never mind one that had the self-consciously edgy safe-sleeze like Tinder, which gave it the sort of underground cachet that immediately precedes mainstream acceptance as all the normies rush in and ruin the vibe. It quickly became the most popular app… and the one that cemented the idea of swipes-as-validation.

See, Match was kind of for squares, eHarmony was for marriage minded people who didn’t want to admit they were using a dating app, but OKCupid had the nerds and the geeks and freaks who were loving the idea that for once they could use their words instead of relying solely on their looks. Fun little quizzes and answering the right questions could give you percentages that suggest just how compatible you were with people you saw – and to a degree, it worked. If you and some anonymous hottie had a 95% match rating, you had good reason to expect that you would at least get a reply to your initial message.

Tinder, however, was openly marketing itself as The Hot People F--k Store, and that set a certain tone. With its focus on pictures, minimal profile text, no messaging unless you had a mutual swipe right, on the other hand, meant that you might never know who saw or didn’t see your profile. You had to hope that your hometown honeys were swiping on you, otherwise you had no way of wowing them with your wit and wisdom. You were sending swipes into the void and hoping to get something back…and that made it clear who was Hot and who was Not.

It also didn’t help that OKCupid was doing “social experiments” on its users and blogging about the data. I’ll spare you my usual rant about sample size errors, a lack of control groups and blatant P-hacking, but their supposed ‘studies’ that were no such thing set a lot of the groundwork for the incel s--tstorm we see today.

The most infamous of these data-driven discoveries was the infamous “who messages who” post on their blog, that helped give rise to the idea that women were only messaging men who were their “equal” in looks.

(They weren’t; in fact, one of things that gets missed is that while women rated men as less attractive than men were rating women, women were messaging a much wider array of men, while men were all messaging women of around the same ‘hotness rating. In as much as hotness can be meaningfully measured in a 5-star standard with no real delineation for looks, personality or skill at making a profile.

I was THERE, Gandalf…)

This helped kick off the wildly misunderstood Pareto Principle into meme legend by trying to apply it to dating: first positing that 80% of the women were first messaging, and then as the original idea continued to be corrupted, dating the top 20% of the men.

And once Tinder monetized things further with benefits like being able to see who swiped on you… well, suddenly you had actual “evidence” as to whether you were one of the Blessed 20 or not. Lots of dudes, taking it as gospel that women were uniquely blessed with attention, while men were struggling for crumbs, would prioritize trying to match with as many people as possible, often by trying to shotgun love into existence. They would swipe right on every profile and then try to decide who they actually wanted to date after the matches rolled in.��Tinder, for its part, started playing silly games too, setting up its internal algorithm that tried to pair the pretty people who wanted to party. The internal ranking system would assign you a score and show you to people who had similar scores – scores based on, paradoxically, how many people had already swiped right on you vs. left and what their score was �– assertive mating done by data nerds. If you had lots of hot women swiping right, your score went up and you were shown to numerically hotter people. In theory, this was supposed to make for better matches. In practice, fives were feeling like they were being told to clam up because a 10 was swiping.

Getting more matches – not dates mind you, matches – became as much of the goal as anything else because it was like a digital data dick measuring contest for dating. Get lots of matches and clearly you were hot stuff. But the problem was – and still is: matches mean precisely two things: jack and s--t, and jack left town. Matches don’t mean a thing if you don’t actually turn them into dates, and that’s where a lot of folks were falling down. Even the supposed digital dimes weren’t getting the dates they thought they deserved.

Since then, the Trouble With Numbers has continued as Match Group has continued to play games with hotness. Everyone on Hinge, for example, has complained about Rose Jail, where they try to convince you to convert by saying “sure, we’ve shown you people we think you’re a good match with but let’s be real: the folks you wanna see are behind this here paywall and you only get one shot per week with them if you don’t pay up.”

Ironically, being put in Rose Jail meant you were often less likely to get messages because people get really squirrely about paying to message people and even squirrelier about getting a SuperLike or Rose or someone paying to talk to you.

So now, the numbers are already dismaying, but you’re also being told that the real hotties, the stars of the show, are waiting as long as you kick in an extra ten bucks per. So, you’re not just getting no-dates from the mid-tier, but the S-tier weren’t even seeing you. And this, on a service that you’re paying for, and being told that it is the way to meet people in the 21st and a half century.

It certainly didn’t help that as the popularity and ubiquity of dating apps grew, the number of people meeting in person wasn’t growing in parallel. Worse, 2020 rolls around and now none of us are out and about, so dating apps are the only safe-ish method of meeting and mating. And since social skills follow the pattern of ‘ashes to ashes, dust to dust, if you don’t take it out and use it, it’s going to rust’, fewer people put in the practice to put themselves into the path of love.

All of which only serves to confirm the confirmation biases of the loneliest, angriest and frequently most entitled awful people who have a hard time understanding that “what, women are things!” doesn’t get you a lot of dates.  

And it’s the entitlement aspect that’s part of what’s leading men to blame women – the same entitlement that keeps framing the male loneliness epidemic as something women need to deal with and solve. Even wags like Scott Galloway who supposedly decry the Red Pill Mythos still validate it when they play into the idea that it’s women’s standards that are causing problems. Certainly not a problem of dudes not raising their game or recognizing that toxic tropes about what makes a man desirable get doubly dangerous when social mobility is a distant myth and the seemingly sole path to prosperity is lined with grift and graft. So start that drop-ship side-hustle, invest in crypto and hope that NFT line go up because that’s the only way you’ll reach the supposed low-end of the “your bank account must be THIS high in order to ride”.

As for what’s to be done: well, honestly, it really is a matter of “go outside and touch grass”. I’ll wave my hands at the overall archive where I’ve written extensively about what guys need to do to get better with women, but much of it can be distilled down to “you gotta live your life in meat space and actually talk to people like a person.” The vast majority of road blocks tend to be self-imposed and helplessness that people don’t’ want to unlearn – to the point that a thirft-store decorated apartment and a small group of friends seems like an unimaginably impossible goal to a truly shocking number of people.

But like I said: it’s numbers all the way down – a 1 to 10 scale in 1s and 0s that started with good intentions and turned toxic the more people focused on the numbers and not the people.

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

DEAR DR. NERDLOVE: My boyfriend and I have known each other since we dated many years ago. We are both “mature” adults. My problem is that BF constantly talks about his (well-used, high milage) “d--k”. Not just to me, but also to others. He inappropriately changes conversations and “jokingly” says things like “Do you want to see my d--k”? He even says this to other men! The last straw came when I was grief stricken and sobbing, because my best friend had died. He started talking about his d--k! I said “Why are you talking about that? He said “I thought it would make you feel better.” I guess that was supposed to replace true compassion and sympathy. I will admit that he is pretty “highly skilled” with his d—k; however, if he tap-danced 24/7, he would probably be a pretty good tap dancer too. What’s up with this?

“Dick’s Chick”

DEAR DICK’S CHICK: Normally I would put my usual “fake letter” disclaimers here, but at this point I don’t think there’s really a question about the reality of this one. But hey, deadlines are deadlines and sometimes a guy’s got word count to hit, so let’s roll with it anyway. ��So, quick question, DC: how old are you and your boyfriend? The two of you may be adults, but frankly, I’m seriously questioning the “mature” part of the equation. For both of you.

This is the sort of behavior I would expect from children who just figured out that saying certain words in public makes the adults squirm or late-teen edgelord prankster wannabes who think they’re cool when they’re really just pizza cutters – all edge, no point. If you’re both old enough to drink or rent cars, I would assume you’re both old enough to have grown out of both acting like this and tolerating it – especially in public.

I also have to wonder what precisely is the appeal of your relationship with your boyfriend, DC. I guess his stroke game must be off the goddamn charts, because it sure as hell seems like he has the emotional intelligence of a turnip. And not a particularly smart turnip. A turnip that’s been held back a few times because it won’t stop drawing big veiny penises all over the chalkboard when its supposed to be solving for X. I mean, maybe I could see some way that he thinks he was being helpful by being “funny” when he was offering you some penis to get you through that trying time. If I squint. A lot. But this is one of those times where not only is intent not magic, but I would question how he made it to adulthood without having certain lessons reinforced by kinetic and percussive reinforcement.

That’s part of why I question whether this is an actual letter or someone’s s--tposting. To be blunt: if I knew someone who consistently acted like this in public and kept dragging conversations to be whether folks want to hear about his magic wand, I would be seriously worried that maybe he has had some sort of stroke or aneurysm that damaged whatever part of his brain that says “hey, maybe don’t talk about your penis to complete strangers, no matter how well used it is.” This is the sort of disinhibited behavior that leads to explaining that Papaw has to go live in the home that smells like disinfectant and despair, with round-the-clock caregivers who make sure he’s not going out into the street and masturbating at the passers-by. At best, it’s a matter of God watching out for fools and Irishmen than he hasn’t had his face pushed in by someone who emphatically did not see the humor in hearing about his junk.

But I also have to wonder why you’re putting up with this or treating it as though it’s a quirky character trait and not a dude apparently itching for a beating or a sexual harassment complaint. The level of this is neither normal or acceptable behavior is off the charts to a degree that makes me question how you haven’t said anything yet. If anything, it seems like you’ve let things go unsaid until it reached absurd heights. Saying that he does this “even to men”, as though this makes it sound as though it was at least “reasonable” that he was talking about it to women but doing it to men was crossing the Rubicon. His unit isn’t like ketchup or mustard; there’s no reason for it to be on the table in the first place without very specific context, and that context ain’t “well, I’m very good with it.” Bringing it up to people who haven’t shown direct, clear and affirmative interest or curiosity is something that just about anyone who’s allowed outside in polite company has been taught, regardless of the gender of the person getting the invitation.

So maybe the question you should be asking isn’t “what’s up with this?”, it’s “why haven’t I told him that nobody wants to hear about his breakfast sausage?”, “why haven’t I said ‘Stop talking about your genitals to other people’ when he does this in front of me?” and “Why in the holy name of Jimmy Dean am I tolerating this behavior and why am I still with him in the first place?” Because I don’t care if he’s the Gregory Hines of f--king, there’s no amount of tap-dancing that will make this sort of behavior acceptable in the public and non-consenting spaces. It’s definitely going to get him in trouble – one way or another – if he continues on like this. Staying with him, especially if you aren’t going to say “what the actual pluperfect f--k is wrong with you?”, means that the odds of your getting caught in the social splash damage keeps getting closer to 1 the longer it goes on.

So – again, assuming this is all real – unless he’s legitimately had some sort of damage to his dome, you should be worrying less about the ‘why’ of it all and focus more on the “knock it the f--k off” side of things. And failing that, dipping out, so at the very least you’re not dating someone whose response to grief is to whip it out and wiggle it at you. 

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