I’m Struggling To Meet People. When Do I Admit The Problem Is How I Look?

I’m Struggling To Meet People. When Do I Admit The Problem Is How I Look?

Estimated reading time: 23 minutes

I wrote in a while ago about whether or not I had to lower my standards. I’ve been trying to go out and meet people, but I find that most of the women I end up interacting with are already in relationships. My friends don’t introduce me to single people, even though I’ve asked. I’m starting to think that single women are incredibly rare and impossible to find.

So, I’ve been trying apps. For a long time. I have professional photos, I talk about my hobbies and interests, I have a good variety of photos and prompts. I’ve had my profile reviewed online and by friends. I send a message with every like I send (I use Hinge). I get zero matches.

At what point do I have to admit that it IS my appearance? You’ve said in the past that sticking out on dating apps is easy, and that the bar is low. I try socializing in real life, but in the meantime the apps seem like a good way to meet people. Thing is, the only people I know who have any success on the apps are either very conventionally attractive or lesbians. I live in a medium-sized city, I treat people respectfully when I send messages, I pay for the app, I try humor, I ask people about their interests and passions, and all I get is silence.

I feel like I’ve done literally everything I can do to improve my dating app profile short of getting plastic surgery and liposuction. I’m still losing weight, but it’s slow going and you said to not wait until I’m thin to try dating. What I have gotten is complete silence from the apps, and meeting people in person is just difficult. It’s not so much that I can’t talk to women as much as single women are rare, and even rarer still are single women that I’m interested in, and of those none of the ones I’ve met are interested in me.

Like, I’ll sign up for a class, and when I show up it’s all old people. I go to a hobby group, and it’s all dudes or their girlfriends. I have friends who I’ve asked for help, and literally everyone they know is already in a relationship. I’ve been told by many people that I’m plenty personable, funny, easy to get along with, etc, but only ever in a friendly way.

Dating apps would be a good avenue to meet people if I could actually get matches. I see people that I have a lot in common with on the apps, but they never like me back. I’ve talked to some of my friends who are women, and they always complain about guys treating them like shit on dating apps, sending dick pics, ditching them on a date, etc. I don’t do any of those things, but nobody will go on a date with me. I know it’s not the case, but it really does feel like assholes get all of the matches. If sticking out is so easy, what am I doing wrong?

Face Time Means Face Problems

Can I ask you a serious question? Do you want the answer to be that your looks are the problem?

No, seriously, I want you to sit with that for a bit and really think about the answer to that. Because the real problem – and the answer to your question – is different, but being able to blame it on one particular issue is often perversely comforting. There’s a sense of release from responsibility when you can point to some immutable quality and say “well, there it is.” It’s one of the reasons why people get so spun up about the idea that women only want to date 6’ tall men or that their standards have become “too high”; it frees the person from having to keep trying and doing things differently and makes it all fait accompli. It’s almost romantic in a very nihilistic, French-New-Wave kind of way; “there is nothing to be done,”, you say while taking a drag on a Gitane while in a moody, black-and-white shot; “the universe, it is arrayed against you. You can struggle against the tides or you can simply accept your place.”

(It doesn’t matter that most of those supposedly immutable characteristics aren’t as immutable as people think or work the way they think it does; it’s about the permission structure, not the facts.)

The real problem, and the real answer is: dating and meeting people takes time, it takes effort, and you have to be willing to tolerate and manage friction. That friction is always going to be there, and the efforts that people take to try to avoid that friction usually only ends up creating new and different forms of friction.

Dating apps are a prime example of this. I’ve ranted on dating apps before, and I’m not going to go over how they’ve changed and why the way they operate now interferes with their stated purpose again; I have a metric fuckton of columns in the archives that have covered that over the years. What I will say is that dating apps are not real life, and are not a reasonable measure of anything that’s broadly applicable to anything outside of “how good someone is at using a dating app”.

But this is where friction tolerance comes in; getting dates from a dating app requires a willingness to put up with frustration, to accept it as part of the price of existence, and to work through it. In practice, it means being willing to experiment, try different approaches to your profile or how you’re connecting with people, even trying different apps that appeal to different demographics, and a certain amount of examining whether it’s worth actually continuing to use them.

To give a concrete example: you’re making a couple classic mistake in how you’re looking at things. Standing out, for example, is the start, not the end of how you get someone’s attention – in person or on a dating app. Standing out gets you noticed, but you have to give them reasons why they should want to engage with you once they’ve noticed you.

This applies to the ways that you’re not as awful as the guys women complain about as well. You list off all the behaviors that women complain about on the dating apps and say that you’re not doing those things. The mistake that you’re making is that the absence of deal breakers or bad behavior is not the same as the presence of attraction or attractive qualities. The fact that you’re not doing the things that turn women off (things that happen after they match with someone, I might point out) is great, but that’s not enough on its own. That’s not giving someone a reason to say “no”. You also have to give people reason to say “yes”. That may mean examining your profile and tweaking and adjusting it. It may mean paying attention to who you’re messaging and how. It may even mean that you’re using an app that isn’t a good fit for you and where the people you’re most likely to click with aren’t on there.

The second mistake is not understanding that while you may not be engaging in the behavior that’s turning women off, the fact that other men are is exhausting them. The more bullshit and bad behavior you deal with on the dating scene, the greater the odds that you’re going to burn out and step away. So, while you’re not making those errors, you’re still having to deal with the effects of the people who are. It sucks, yes, but that’s life and we don’t live in a vacuum. Sometimes the problem is that other people are assholes and you happen to be around at a time when folks have been exhausted by all the assholes and they’ve bounced for a bit.

The former is something you can work on. The latter is something you just have to deal with. In both cases, it’s a matter of friction tolerance. You have to find ways to be cool with both if you want to use the apps to meet people.

But dealing with friction doesn’t mean putting up with pointless bullshit; it means paying attention to whether the amount of bullshit you have to put up with is at all commensurate with what you get out of it. I suggest people relegate online dating and dating apps to being a supplement for meeting people for precisely that reason. The effort you’re putting in isn’t just trying to meet people, it’s trying to navigate around all the additional restrictions and barriers the apps put in place because their goal is to frustrate you, so that you’ll pay to be less frustrated. They’re trying to find the sweet spot of annoying you in order to get you to convert as a customer but not being soannoying and frustrating that you quit the app entirely.

It doesn’t take long before the ratio of friction-to-reward becomes unbalanced, and so it makes more sense to deprioritize the thing that is causing more frustration than success. At least meeting people in person means that you’re out, putting yourself into fortune’s path by increasing the ways that you might meet someone instead of hoping that the algorithm is going to line up just so and the massive gender imbalance in the apps’ customer base doesn’t get in the way.

Meeting people in person still means dealing with friction… but it’s different kinds of friction, and friction that doesn’t come about as the result of someone trying to monetize your frustration. And it’s often friction that’s easier to deal with because the benefits are greater than just “do I get a girlfriend out of this or not?” Once you expand your interests beyond the narrow focus of “get a girlfriend”, it becomes easier to deal with the issues that may come up.

Case in point: there’s the issue of “right time, right place, right person”. Someone might be a great match for you, but if you’re not in the same place where they are, it doesn’t matter. Or you could meet them, but they’re not necessarily at a time in their life when they are available to date. If all three factors don’t line up – and there’s no way to guarantee they will – then things aren’t going to click.

Similarly, some of the friction comes from the simple fact that you’re dealing with other people; you can do everything “right”, but people won’t respond the way that you expect. That’s the nature of humanity and individuality; we’re not social robots who follow a strict linear flow of cause and effect or stimulus and response. So, you have to deal with the fact that sometimes people aren’t going to rock with you in the way that you hope, no matter what you do. It blows, but it’s life.

This is part of why meeting people in person is both playing a long game, but also about thinking beyond just who’s in the room with you. If you’re a regular reader, you’ll likely have seen me say that “you may not be meeting your next romantic partner at that meetup, but you may be meeting the person who’ll introduce you to them.” Sometimes that’s very literal – they introduce you to their single friend and you’re off to the races. Other times, it’s indirect; by being in their social circle, you create the circumstances that will bring you together with someone who is right for you, who’s available and looking. At that point: it’s all up to you to make the magic happen.

So, while the people you’re meeting at the various events may not be the folks you’re hoping to meet, having them in your life as friends (or at least as part of your network) increases the odds that you’ll meet the right person.

This is why I’m a big believer that the luckiest people are the people who are out there actively looking for fortune to strike. That is: they’re the ones who are doing the things that make it more likely that they’re going to encounter Mr./Ms./Mx. Right. That means going out, being social, talking to people, building connections and being open to serendipity.

It also means being willing to endure the friction of “sometimes you just gotta wait”. Or “sometimes you have to build up the friendship meter the long way before you can get to where you want to be”. Or saying “ok, well, the people who were at the meeting this time weren’t who I wanted to date, but I enjoy this anyway, so I’m going to keep coming and see what happens”.

That’s why I tell folks to do things that engage them and that they enjoy, rather than taking classes or going to events that they dislike. It’s a hell of a lot easier to handle the friction when you’re actually enjoying the activity or the group. And if you’re there because you enjoy the group, rather than solely because you’re trying to meet a potential date, you increase the odds ofmeeting someone who would be a potential date, because you’re being your authentic, joyful self, who’s fully engaged with the group. That’s far more appealing to someone who shares your interests, and it means that when you domeet a potential special someone, you’re more in the moment instead of being lost in your own head and focusing more on trying to impress them or win them over.

This, in turn, is why “it’ll happen when you least expect it” is a true, if unsatisfying answer. It’s incredibly easy to let the friction affect you so much that it starts to impede your ability to connect with people. It’s very similar to getting stuck on a particularly difficult boss battle or level in a game; you get frustrated, you get sloppy, you make mistakes, which makes you more frustrated, which makes it even harder to focus. But if you take a step back and do something else for a while – in game or out of it – and then come back to the challenge, you often find that the time away has reset your frustration and you’re able to attack it with renewed focus and skill… and then suddenly you are able to overcome that boss with ease.

This isn’t just friction tolerance, but friction management. You’re not just enduring the frustration, but taking steps to lower your overall sense of frustration by changing your focus, your goals and where you’re spending your time. Yes, I know that when you’re lonely or you’ve been single for longer than you would prefer, you want that to change as quickly as possible. But, again, this is precisely why friction tolerance and management are vital skills; that desire for quick results gets in the way and makes things worse.

Now is this a satisfying answer? No, probably not, because “here’s something else you need to work on” isn’t what you want to hear. But that’s the thing: it’s not “something else”; it’s part of the whole. Dating and socializing aren’t discrete parts of your life that can be segmented and siloed off; it’s part of the holistic nature of you and who you are. It’s a little like cross-training; you’re doing different things that all combine to create a stronger outcome than the sum of its parts. And, like many forms of cross-training, you combine what you’re doing in order to grow and improve more efficiently.

Going out and doing things you enjoy that help you meet other people who enjoy those things improves your social skills, increases the number of people you’re meeting and gives you opportunities to build relationships. Some of those relationships are going to be platonic. Some of them have the chance to be sexual or romantic. Spreading out your attention and having a broader overall goal – instead of just “I need to get a date ASAP” – makes it easier to tolerate and manage the friction of trying to date. And that increases the likelihood that when you do meet that special someone, you’ll be ready to take full advantage of the moment.

As I always say: nobody said it would be easy. They just said it would be worth it.

Good luck.

Doc,

What the hell is wrong with me?

I genuinely don’t understand why I seem incapable of building lasting friendships or meaningful relationships, let alone having any success romantically.

The hardest part is that I have no idea what I’m doing wrong. I am kind, considerate, approachable, and someone people feel comfortable around. I enjoy making people laugh, I listen, and I do my best to leave people feeling better than I found them. I look after myself, have hobbies, and I’m considered attractive. My interactions with other people are almost always positive, which makes this so confusing because I have tangible evidence that I can build trust and have a positive impact on people. For example, I’ve spent years working with the younger generation, and when I recently left one of those roles, I was overwhelmed by the sheer number of messages I received. Many of them had only known me for a few months, yet they wrote about how I’d helped them through difficulties, listened without judgment, or made a genuine difference in their lives. That doesn’t exactly fit the image of someone who’s unpleasant, creepy, or impossible to connect with.

However, whether in a professional setting or a casual one, my relationships with other adults rarely progress beyond surface level, and almost none of those connections ever develop into genuine friendships.

I’ve been attending the same social hobby for years. Everyone knows who I am, but I seem to exist on the edge of every group. I watch people naturally fall into conversations, make plans, become part of each other’s lives, be friends on Facebook, all the while I never quite become part of anyone’s circle. I’ve made the effort. I’ve invited people out, started conversations, and tried to build relationships, but it always feels one-sided. If I stop trying, the connection usually disappears with it. I’ve tried other hobby groups over the years, with the same effect.

And then there’s dating. I get on well with women and treat them as I would anyone else. We laugh, chat, have good conversations, and I can be playful, but I always seem to end up in the same category: someone who’s nice to be around, but never someone they’re interested in romantically. It’s bloody frustrating, especially when people assume I’m popular with women simply because I always seem to be surrounded by them or because I’m having my picture taken with a group (so, on the bright side, I have “social proof”).

I’m not cruel. I’m not manipulative. I’m not someone who deliberately pushes people away. So why do I always end up alone? Why do I find myself sitting on my own late at night, in a field, crying my eyes out and screaming out in frustration, wondering what everyone else seems to understand that I don’t? It’s painful!

At this point, I genuinely don’t know what’s missing. If there’s something about me that stops people from wanting a deeper connection, I wish someone could tell me, because from where I’m standing, it feels like I’m doing everything I reasonably can, and it still never seems to be enough.

Wrong Side of Right

There’re a couple of things to consider, WSoR, and part of it is recognizing that the nature of the interaction you have with people is going to affect how they see you. It also means that results in one interaction don’t necessarily count towards gauging other interactions; the credits just don’t transfer.

There’s a difference, for example, between the relationship a mentor has with his mentee(s) and the relationship with friends. While a mentor can become a friend, the skills and behaviors that make someone a good mentor are not the ones that necessarily lead to more friendships with people outside of that mentor/mentee dynamic. There are a whole host of differences, such as the inherent power/status dynamic between a mentor and the person they’re mentoring, which isn’t going to be present when you’re making friends or finding dates.

That doesn’t mean that what you’ve accomplished with younger people isn’t impressive or that you shouldn’t be proud of it! You absolutely should. It just means that there isn’t a 1 to 1 correlation between “good mentor” and “good at making friends”, and it’s not a reliable indicator as to what you may or may not be doing wrong.

The same thing applies to the things that you’re not. Like I said to Facetime Means Face Problems, an absence of drawbacks isn’t the same thing as the presence of merits or desirable traits. Every relationship, whether romantic, sexual or platonic, isn’t just about keeping your foot off the brake, it’s about putting a foot on the gas; you have to give them reason to want to spend time with you, not just be an absence of reasons to avoid you.

It’s a little like being “nice”. “Nice” is, well, nice, but it’s not necessarily appealing. You want to aim for more than just pleasant. You want your presence in someone’s life to be actively enjoyable for your being there. That comes in many different forms, but all of them involve how you make people feel when you’re around. Many times, the people who struggle with “you seem like a good person but I’m not feeling the spark” is that they’re not actually giving that person anything to spark off of.

While spontaneous chemistry is a thing, most of the time, chemistry has to be built through behavior and interacting. Helping someone have a good time while showing interest and inviting a response is part of how you build chemistry. I can have a perfectly pleasant time talking with someone about, say, our cat’s crazy antics, but that’s not likely to lead to a date. But that, combined with mutual flirting or other activities that engage them more than just on an intellectual level very well might. It’s the combination of removing the breaks while applying the gas – having reasons to say “yes” while removing reasons to say “no” – that makes the difference. One without the other simply doesn’t work.

But let’s talk about having a hard time making deeper connections, despite having these positive qualities and a lack of negative ones.

One of the things I notice with folks who have a hard time making deeper connections is three-fold. One is that they are often not allowing other people to go beyond the surface level – certainly not in a way that folks would appreciate. Many times, the issue is that they never really get beyond small-talk and into more meaningful conversations. Now, before people start saying that this is why they hate small-talk, the thing to realize is that the point of small-talk is to establish a consensus of reality and gauge not just compatibility but surface-level commonalities. That is: you’re learning about them, finding out whether you vibe, and what things you have in common that might lead to deeper, more meaningful conversations.

The problem is that people who seem to struggle making friends don’t transition well to those deeper conversations. Most of the time, the conversations don’t get any deeper; when they do, the conversational bid is often a little too deep or done in a way that feels inappropriate. It’s a little like establishing that you both really enjoyed this season of Widow’s Bay, but then one person launches into how life hasn’t been the same since their grandmother died.

It works better to use those early, simpler commonalities to find other commonalities that veer deeper – ones that are more indicative of shared values or interests, ambitions or goals. Talking about Widow’s Bay, for example, could lead to talking about shows, books or games with a similar feel – the Alan Wake/Control games, shows like Twin Peaks, folk horror and the like – and what draws you to them in the first place. This, in turn, makes it possible to talk about other, tangentially related interests or values; if watching certain shows or reading certain books made you decide you wanted to be a writer, or that you enjoy X because it’s a distraction from Y.

This leads to the second problem: you have to show folks that you’re interested in them. Not by inviting them to do things, necessarily, but showing that you pay attention and that you care. One of the reasons why Tom Cruise is so magnetic and charismatic is that not only does he make people feel like the most interesting person in the room, but he remembers things about people and asks about those things. He’s famous for remembering little details like a grip or PA mentioning that their brother or cousin had a big exam coming up and asking them how it went, or inquiring after their wife or husband. The fact that he not only paid attention but cared enough to ask about it later makes people feel incredibly special and seen, which endears him to them.

Asking about things that your acquaintances had brought up before or mentioned in passing, asking how things are going in their lives that goes beyond “what’ve you been up to” all makes a real difference in how people see your relationship to them. You’re showing that you’re interested in them as a person – not just as a fellow fan of whatever or someone who also enjoys the same hobbies. That is part of what leads to a friendship being about more than just being activity buddies.

You need to also be willing to share about yourself as well. The easiest way to do so is using the method I mentioned earlier: relating in some way to the shallower topics. Explaining how you got into a particular genre or what that fandom lead to, or how this was tied to an ambition of yours or a person who introduced you to it… these are all little tidbits of information for the other person to pick up on that don’t feel overwhelming or inappropriate. It allows them to get to know you as a person, first in context of your shared interests and then in the context of someone they like spending time with.

The third thing is that it takes time to make friends, and that time isn’t always immediately obvious. The people who seem to fall into effortless conversations and make plans tend to be ones who’ve already put in that time when you weren’t there to witness it. While there’s always the chance that some folks had immediate chemistry – again, it does happen – that made developing a friendship quickly, most of the time, they’re people who have some form of pre-existing relationship that they’re building on. They may know each other from before you joined the group, have connections outside of where you met them or otherwise simply have had more opportunities to grow their connection to one another.

Often, the reason why it seems like people can’t quite crack the barrier of connection while other people do is simply because it’s too early or too soon. The level of your relationship simply isn’t there yet, because you haven’t spent that much time together, building it to that point. They may not feel like they know you that well, or that your connection – though growing – is at the point where they’re necessarily ready to meet up with you outside of the activity or venue. That’s ok; it just means that you’re still working on getting to know each other and building that connection.

The thing that often trips people up is that the time it takes to get to that point isn’t just being in each other’s physical presence; it’s in how often you interact and how. Spending more time talking one on one at the meetup or talking in a group helps build that connection; being at the same event but not interacting much, if at all won’t do it. The latter may mean that you’re someone to nod at, someone they recognize, but the former makes it more likely that they’ll seek you out to talk to you or think about inviting you to an event that they’re hosting.

But a thing to consider is that part of getting to the point where you’ve spent enough of that time that you’re moving past acquaintance and into casual friendship is that sometimes you have to be the one who’s being proactive about it. This means that yes, if you’re not actively pursuing and maintaining that connection, it’s going to fall apart. This doesn’t mean that they don’t like you; it just means that you haven’t reached the point where you’ve got that foundation of a relationship that will hold up on its own. Yes, it can be frustrating when it feels like this early acquaintanceship is one-sided, but that doesn’t mean that it always will be. It simply means that not everyone is going to have the time, energy or bandwidth to give equal attention to everyone who’s asking for their time. It’s not a lack of interest so much as “you can’t spread your attention equally to everyone at all times”. So sometimes you have to be the one willing to take the lead until you reach the point that you’re now someone they can or want to connect with.

Is that frustrating? Of course. But as I said earlier: you need to learn how to deal with and manage friction if you want to exist in the world.

Now, maybe there’re some underlying problems that you aren’t aware of or some way that you’re coming across to other people that’s getting in the way. Maybe you’re having a string of bad luck in finding groups where you simply just don’t vibe. But if you’re generally well-liked and well-regarded, the odds are good that the issue is one of time and the deliberate building of a connection, not some inherent flaw.

Focus on the changes I mentioned and I think you’ll see a difference in how your relationships develop.

Good luck.

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