How Do I Stop Wasting My Time Trying to Meet People?

How Do I Stop Wasting My Time Trying to Meet People?


Estimated reading time: 14 minutes

Dear Dr. NerdLove,

Just wanted to start by saying that I have been reading through your blog a lot lately. I feel like that this is one of the few blogs that I have read that addresses real questions by people who struggle in dating and provides practical advice. As I have struggled to find advice among peers, I thought I might get help from you.

A brief summary of my early dating history. I was a depressed teenager who suffered from hypothyroidism. I got my health fixed and struggled in dating in my early 20’s due to my lack of experience. This led me to pick-up artistry. I didn’t have malintent, but obviously I wasted a lot of time dating toxic and incompatible women.

This all changed when I was 23. I met a wonderful woman who approached me when I was literally walking down the street. Let’s call her Ashley. Ashley was kind, pretty, smart, and loved me for who I was. She was older than me (32), but she was patient with me in my inexperience and helped me sort through a lot of my issues. Long story short, while we had amazing chemistry, we had different values systems and so our relationship didn’t last.

Ashley and I ended things a year and a half ago. I understand why things had to end with Ashley, but it has affected my dating life. Ashley treated me well, put forward a lot of effort, and constantly told me she loved me for who I was. Early on, she would tell me how attractive I was and how she was always excited to see me.

I feel like I am in a weird spot. I have been on a few dates since Ashley and met a few other girls, but nothing seems the same. Not that I am hung up on Ashley, but don’t feel like putting forth the effort since I feel like when I make the effort they are not interested. I haven’t been out on a date in a while now. The only time things have ever gone well in my dating life was when women approached me or made a significant amount of effort.

The thing is though, I am torn because I know women don’t normally approach, but when I approach it usually goes badly. I try to talk to women, but they usually don’t hold conversations. I do get approached by other women, but that usually happens a few times a year on average.

I always get the same advice when I ask my friends for help. It is either them telling me about my job, my looks, my material possessions, or that I am a great guy and women would be lucky to have me, or I get the classic “It will come when you least expect it.” After a significant dry spell, I have decided that I am looking for something a little less fatalistic.

Am I a victim of my high expectations? Is there any advice that doesn’t involve being a sitting duck? How do I keep a balance of not putting too much expectations on women to like me off the bat, while also not wasting time with disinterested women?

Back In The Saddle

There’s a lot here, BITS, but this is a case where it all really comes down to one thing. And that thing is the ratio of effort to reward. You’re understandably frustrated that the level of effort you’re putting in isn’t commensurate to what you’re getting back. It’s understandable that this makes you less interested in actually putting in effort in the first place.

But here’s the thing: the real issue isn’t the ratio of effort to reward, it’s the kind of effort you’re putting in and the way you’re doing it. Part of the reason why you’re getting frustrated is that you’re going about things in a way that’s far less efficient and less effective than others. And if you can be anything, you should be efficient.

Fortunately for you, the answer is in your letter already; you (like many people) are just misunderstanding it. It’s also something that you’ve already experienced.

I’m talking, of course, about the classic “it’ll happen when you least expect it”.

The thing about “It’ll happen when you least expect it” is that it doesn’t mean “sit around, cross your fingers and wait”, it means “go about your life and do other things so you don’t get burned out, and you’ll be more likely to run into folks you’d want to date.”

It’s about taking a break from an activity that’s becoming a chore and being open to serendipity.

Consider how you met Ashley. You weren’t actively looking. You were just out doing your thing and she approached you. This, literally, happened when you least expected it. But it was because you weren’t expecting it that it was possible. You were in a place where you were capable of responding to an opportunity that presented itself, but because you weren’t actively looking, you were in a more relaxed headspace. This meant that not only were you being more authentic and in the moment, but you were also not worried about achieving a particular goal or outcome. That made everything easier.

Think of it this way: how many times have you been playing a game where you’ve gotten stuck on a particularly nasty boss fight? Every time, you get absolutely bodied and to add insult to injury, the last checkpoint was a good ten minutes before the boss. So now you’re trying to rush back to the fight, just to get beaten like a kettle drum and then you get so frustrated that you’re getting sloppy and now you’re getting taken out by the grunts before you even get to the boss fight.

Then, instead of seeing how far you can embed your controller in the drywall, you set things down, turn off the console, go for a walk, take the evening off and generally just give yourself a break. Then you come back to it a day or two later and… well shit, you just blazed through that fight like it was nothing.

What happened? You gave yourself a break. You let your brain relax and unclench, you gave yourself permission to not worry about this incredibly frustrating thing and that let you reset yourself to a better place. Then when you came back, you were ready, rested and able to take on the challenge without a haze of exasperation.

This is one of the reasons why I tell people – especially folks who’re coming from a red-pill or PUA background – to change up how they’re meeting people. Part of the problem is when you (the generic “you”) are doing “approaches”, you’ve given yourself a fail condition: you succeed (get a number, get a date) or you fail (you get nothing). By definition, this means that you’re invested in the outcome, which means that now you’re not being authentic. You’re trying to achieve a goal, and that goal is “try to convince this person to like me enough to go on a date with me.” 

This is not the goal you want to have. 

The problem is that when you have this mindset, you’re focused on the end result, not the person as a person. You’re often far too busy trying to plan the next thing you want to say or trying to read the tea leaves, rather than just trying to get to know them. You’re (again, the generic “you”) also often coming from a place where you’re trying to justify your interest in someone and trying to win their approval. The problem is: you don’t know if they’re worthy of your approval. You know nothing about them except that you find them attractive. So you’re coming to the interaction from a place of insecurity (“please like me”), giving them more importance than they’ve actually earned at this point and you’re worried about the outcome more than the quality of the conversation. This creates a situation where, even if things work out, it won’t be great in no small part because you’ll have a much harder time ever feeling secure in whether they even like you all that much.

So, taking this back to “it’ll happen when you least expect it”: the best way to put this into practice by going about and living your life in ways that just bring you in contact with other people. Ideally, you’re doing things that you love in ways that will help you meet other people who also enjoy those things – an instant commonality and easy point of bonding. But even if you’re just out trying something new or just wandering around, being relaxed and open to whatever comes your way makes everything much easier – both in terms of creating a connection, but also in terms of not psyching yourself out and putting more barriers between you and other people.

The key here is to not “do approaches”, it’s to just be social with everyone. Being curious about folks and wanting to know more about them works far better – both in terms of the connection you create but also the mindset you’d be working within – for forging connections with people because you’re not focused on the goal. You’re just talking with people without any real outcome in mind. If you have a good conversation with an interesting stranger? Excellent! If you get a date or exchange contact info with someone you find hot? Even better! And if things go nowhere and they’re not holding up their end of the conversation? Ok, well, it’s a shame, but that just means that they’re not someone you need to expend any more time or energy on.

That relaxed, open and friendly attitude also translates into making you more approachable by others. As I’ve said many times before: nobody is going to be so invested in a stranger who’s giving “do not disturb” signals that they’re going to ignore all of those and try to forcibly drag him out of his shell. They’re just going to assume that he doesn’t want to be bothered. Someone who’s giving off an attitude of warmth and approachability, being friendly without having an obvious agenda? That’s a person who’s far more likely to have people who’ll say “hi” first. And this could be as obvious as someone literally coming over to say hello or someone using an observation or comment to get the conversation started.

Someone who comes over to compliment your shirt or your glasses or tattoos? That’s often someone who’d be interested in talking a little. And other people who see you being friendly and talkative will know that they are likely to get a warm reception too if they were to say anything. Or if you were to talk to someone else, they would also know that you’re a sociable, friendly guy.  

Be more social and be willing to talk with folks, including people you aren’t interested in dating. Be curious, get to know them, find out what makes them tick and what makes them cool. Find out whether they’re someone who’s worth your time, rather than worrying about convincing them that you’re worth theirs. This will dramatically up the number of times you meet people who you enjoy talking to and increase the likelihood of someone else coming over to talk to you.

It also means that you’re more likely to get a positive response from people when you ask them out. If, over the course of this conversation, you feel like you’re catching a vibe, it’ll be the most natural thing in the world to say “hey, I’m really enjoying talking to you. I’m doing $COOL_THING this weekend and I think you might really enjoy it. Would you like to go?” That feels vastlydifferent than a guy who’s only at the coffeeshop, dance class or whatever to get dates… and is more likely to be both appreciated and welcomed.

Good luck.

Dear Dr. NerdLove:

Brief context, working towards dating again, it’s been a few years since my last relationship ended. I’m in a new city, and don’t already have friends here. That’s not what I want to ask about though, you’ve covered most of the basics on social skills, presentation, and building confidence elsewhere.

What I did want to ask about is, should I be on social media? Earlier in my life, I didn’t use Facebook because I wasn’t very social, and didn’t see much point in it. I had friends I met in High School, and met my first girlfriend in college. But now finding myself in a new place, and building friendships and hopefully dating starting from nothing, I’m wondering if I should rethink that. Is this something people will expect to see? Will it seem odd not to have social media? Am I holding myself back by not being on social media?

The reason for asking, instead of just proceeding, is that my reasons for not having social media have changed. This isn’t the place to go into detail, but I have a strong dislike of their business practices (privacy violations, the entitled attitude that any information about your life belongs to them to sell to advertisers, anything is okay as long as it makes money, etc.), to put it simply. I’d rather not support companies like Meta if I don’t have to. But sometimes the world doesn’t really give us choices, if this were truly something that is going to be a barrier, I suppose I’d put it down as a battle to fight another day.

And yes, I’m fully aware similar such objections can be raised about many, many other things we (and I) use every day. But I suppose this one gets to me more than others for some reason.


Social Media Luddite

You don’t need to be on social media if you don’t want to, SML. If you want to maintain a principled stand against Meta and other big corporations, by all means, do so. There’re even some good resources on how to avoid using apps tied to them; Cory Doctrow talks frequently about how to break away from big tech and bring down surveillance capitalism.

And honestly, I understand the feeling that holding out against Meta when others are just as bad can feel like selective outrage. However, there’s just so many places where you can’t opt out for varying reasons that it’s understandable to go all Picard and declare that THE LINE! MUST! BE DRAWN! HERE! in a place where it is feasible to refuse to participate.

(Also, there’s a certain amount of ‘horse-having-left-the-barn-already’ with regards to your data. Facebook is very good at identifying and tracking people by proxy – by looking for the person-shaped hole left by their friends who are using their services. So if you decide you need a permission structure to join Instagram or whatever… there you go.)

Will people think you’re weird? I mean… possibly. There will likely be folks who are somewhat discomforted by not being able to learn more about you online. Googling people, checking their Instagram grid and so on is fairly standard practice – out of curiosity, out of a desire to check to see if you’re who you say you are or to see if any obvious red flags pop up. Not having as big of a presence online means that there’s less for people to see… but that also may mean some folks may worry that this is a sign that you’re hiding something.

This tends to be more generational – Gen X is less likely to find it weird than young Millennials and Gen Z – so that may be a consideration. However, with the increasing awareness of just how much Meta and other companies mine and abuse our data, a lot of people would also get it. It might not be a stance that they could see themselves taking for a lot of reasons… but they’d get it.

But I wouldn’t worry about that. I honestly don’t think there are enough folks who would take this as a red flag that it would meaningfully hinder your chances of meeting people. I think the bigger issue would be about convenience and staying in contact with folks. That might be a challenge that’s harder to overcome.

The thing about social media and its relative ubiquity is that it gives you more areas with which to stay in contact, to make plans and otherwise conduct your social life. Instagram is one of the biggest apps in the world and a lot of people use it for staying in touch with their friends via its DMs. The same goes for WhatsApp; it’s a Meta property, but it’s also how a very, very large population stays in touch. For many people, it’s functionally the entire Internet. Not using those cuts down on ways of staying in communication with people – especially as folks are less and less inclined to talk on the phone.

There are non-Meta affiliated options like Signal or Telegram, but they don’t have the same userbase, are less likely to be used by folks who you might want to date and are less intuitive to use. So you may well find yourself having a harder time staying in touch simply because you don’t have a presence on the apps they use.

The same goes with planning. A lot of folks I know stay on Facebook in part because it makes it a lot easier to organize parties or events – having one place where folks are able to RSVP, ask questions, or where you can update everyone at once about any changes is incredibly convenient. Yes, you can always use third party services like Evite and the like, but again: the ubiquity of Meta and Google and the like make it more convenient.

At the end of the day, I think the question of whether to use social media is going to come down to convenience and utility more than anything else. If you’re dating people who are more comfortable texting or calling, then clearly this will be a non-issue. You’ll just have to decide if the trade-off of privacy (and principles) for convenience and contact are worth it for you.

Good luck.