I Can’t Get A Date… What Am I Doing Wrong?

Hey there Doc,

My trouble is that I don’t know how to go about dating because I don’t understand how to get to know potential partners and have them be positive towards me as well.

Little introduction to me: I’m 25 years old, Never had a relationship or even things like a first kiss, finished my engineering degree in 2021 and currently at a temporary job while finding something longer-term. While studying I was in some local clubs, but moving during a pandemic shut that down. I have broad interests, spending time on all kinds of different hobbies. I play D&D, am learning some music production on a hobbyist level, I used to play volleyball a lot (and want to again) currently I mostly go to the gym to keep active. I have great friend groups both online and offline. The online ones especially helped greatly during the pandemic isolation times.

So far so good. I like where I am, I like where I am headed. My trouble is that I don’t know how to continue trying to date. I want a romantic partner, but so far I’ve only gotten rejection, no matter which way I tried.

I tried cold approaches, where the best reaction I got was a “no thanks”, and more people were uncomfortable than not, so I stopped. I tried warm approaches if I met someone in a friend group or club, responses ranging from “lets just be friends” to offended. I also tried online dating multiple times over multiple years, and have gotten exactly one conversation out of it, where she stood me up on our supposed date then ghosted me.

My problem now is: I don’t know what I am doing wrong. It HAS to be a me-problem at this point, I refuse to believe that everyone else is just wrong. If I’m talking to my friends I mostly just hear “you are doing it right, you are just unlucky”, which would be fair if we were talking about 1 or 2 experiences, and not literally all of them through 7 years.

I know the classic response is “be yourself, be authentic, be confident, get to know more people in non-dating environments” but what do you do if that doesn’t work? What do I change? Obviously at this point it’s also extra hard to keep confidence up. I used to be more confident in myself, but that also didn’t help with getting rejection and never positive feedback, so that crumbled over time.

Which is also a little weird because I used to think I was pretty good looking, I know I am a pretty good person overall. If I was a potential partner for myself I would like me is basically what I am saying. But then why doesn’t anyone else seem to like me? What do I need to change? Should I focus more on one or two of my interests and just drop the others? Should I go for more cold approaches again? Should I just live with being undateable? Is there some other way I am missing?

The only things I know are; first: that I don’t want to continue trying to date the way it’s going right now. Second: that I want to find a partner. How do I get those together?

Best regards, lots of love for the advice you give out.

Spinning My Wheels

Questions like this are frustrating, SMW, because there’re too many possibilities and not enough data for me to really weigh in. The way you’ve laid things out here, the only way I could really answer your question would be to follow you around like a relationship Richard Attenborough filming a documentary on rare woodland creatures.

So, instead, let’s talk about some of the likely problems, especially based on what you’ve told me.

First and foremost: yes, sometimes you can just have shitty luck. Yes, even for years. I’ve had friends who had multi-year long dry spells and unbelievably bad experiences when they did find dates. In those cases, I actually did follow them around and on a few occasions, went on practice dates with them. Almost every time, they weren’t doing anything wrong; they were just having a bad streak that had more to do with the dating culture than anything else. All of them considered just giving up on dating and all of them have since gotten into long-term relationships, including marriages.

Yes, I know that’s not the most satisfying advice. But sometimes it really is a case of “if you’re going through Hell, just keep on going”; sometimes the best move is to grit your teeth and white-knuckle your way through to the other side.

But if I’m being honest: the reason why your friends told you that is likely because they didn’t know what else to say. Much like “just be yourself” and “It’ll happen when you stop looking for it“, it’s the sort of thing we tend to toss out there when we don’t know what to say, but feel like we need to say something besides “that’s rough, buddy.”

So instead, let’s talk about what you can do differently that would improve your odds. First and foremost: you apparently need to adjust your approach. One of the things that leaps out at me is that you say that either people you’ve approached react badly or get offended. This, I think, is likely your biggest sticking point. If it really is the case that folks were getting offended by your asking them out and not just your jerkbrain rounding their mild reaction up to “catastrophic”, then the odds are good that you’re going about this the wrong way.

One of the first questions I would have is “exactly how are you approaching people?” If you’re doing cold approaches, just where and how are you doing them? Are you talking to folks at times when it’s more acceptable to hang out and talk? Are you focusing on having actual conversations and gauging people’s interest? Or are you charging in like Ataru Moroboshi out of nowhere and trying to get strangers to give you their number with no preamble?

(Google it, kids)

If you’re approaching someone in your social circle or who’re part of one of your clubs or hobbies, who are you approaching and what are you saying? Are these folks who you have an existing relationship of some sort with, even if it’s just acquaintences? Are they folks who have been showing interest in you or people that you’ve caught a vibe from when you’ve been hanging out with them? Are you asking them out on dates that are unmistakably dates?

In fact, are you asking them out on dates, or are you leaping straight to “I’m looking for a girlfriend, how about it?” Because if you’re more focused on the “getting a romantic partner” part, your issue may well be that you need to slow your roll way the hell down. I know a lot of folks who try to speedrun the dating process and that just doesn’t work. The early days of dating are very much about getting to know each other and trying to determine if there’s enough mutual interest, chemistry and compatibility; part of the point of a first date is to see if you’re interested in more, after all.

As a general rule, regardless of whether you’re doing warm or cold approaches, you want to focus on connecting with people and having a good time with them. One of the single most reliable indicators as to whether someone will go on a date with you is if they have fun talking to you. The  more someone enjoys spending time with you, the more they’re going to want to keep spending time with you. We instinctively prioritize our relationships  with the people whose presence makes us feel good, appreciated or valued; this is what’s known as The Reward Theory of Attraction, and it’s incredibly powerful. When Jessica Rabbit says the reason why she’s into Rodger is because he makes her laugh, she ain’t lying; a good sense of humor is incredibly attractive because of how it makes folks feel.

And if people are actually offended by your asking them out dates – not just “I had one person get upset at me for seemingly no reason”, but multiple people being genuinely offended by what you said or did? Then it’s time to ask some of your friends to be brutally honest about how you’re coming across to folks who don’t know you well. That would end up being something to zero in on as fast as humanly possible.

Another important question is how much time and effort you’re putting into reading the room and looking for actual interest. Part of what trips folks up is that, when they go in completely cold, they usually have bad luck because… well, because they chose to hit on someone who wasn’t even remotely interested in them. Watching for signs of interest and prioritizing folks who like you and want to spend time with you is an important part of upping your success. The way folks get this wrong is that they look for far more intense or over-the-top signals than the majority of people will ever see. It’s not about looking for someone who’s been eye-fucking you from across the room all night – though if you encounter that, then go talk to them – it’s about less obvious signs. Someone who gives you a long smile when you make eye contact, for example, is a good sign. But so too is someone who always seems to be hanging around you, waiting for you to notice. Or the person who always laughs at your jokes, even when you’re pretty sure it wasn’t that funny. Or the one who’s showing more than casual interest in what you’ve been up to and what plans you may have coming up.

Now the unfortunate truth is that social calibration is the sort of thing you refine through practice, experience and, yes, getting shot down. So part of doing better at dates is being willing to put yourself out there, make mistakes and to learn from them.

But let’s say that you’ve got most of this on lock. Ok… what next? Well, this is when you live by the maxim of “if you want things to be different, you have to do things differently”. That means you need to start changing things up and figuring out what works for you and what doesn’t. One of the mistakes that a lot of guys make is that they tend to get stuck in ruts. They stick to doing the same things over and over again, partially because it’s all they know, but partially because they feel like they shouldn’t have to change their approach. A lot of times, they won’t make more than a token effort at doing things differently and, even then, not for long. More often than not, they’ll do something differently for a day or two before going back to the way things were in the first place because the new stuff didn’t work instantly and it was uncomfortable and weird. And hey,  that’s understandable. Getting out of your comfort zone is difficult! Unfortunately, it’s also necessary. Your comfort zone is frequently a bad basis for comparison; just because something’s familiar doesn’t mean it’s what you need.

One of the changes might be who you’re approaching. Sometimes we aren’t pursuing the folks who we actually want to date so much as who we think we should date. Sometimes this means that you’re pursuing folks who you’re not actually interested in because of what your friends might think. Other times it means you’re approaching people you find less intimidating or “easier” to talk to, but not folks that you feel strongly about. And since people can tell when they’re not your first choice, that tends to backfire against you in a big way.

Another might be your style and presentation. Yes, you can have good bone structure and a strong build, but a bad hair cut, poor skin care and ill-fitting, non-stylish clothes can undercut all of that. This is another area where folks tend to get stuck in ruts because they’ve locked themselves into a particular style, size, hair cut or what-have-you for years or even decades. Making those changes can seem like a betrayal of who you are – you’re not the kind of person who wears those cool clothes! – or requires that you try colors and sizes that you might never try unless you were pushed into it. But again, just because it’s familiar and comfortable doesn’t mean that it’s a good look for you. And as I’ve said many times before: a simple hair cut and a basic skin care regimen can utterly transform how you look, virtually overnight.

And one last thing to consider: ask your friends for help. I don’t mean “ask them what I’m doing wrong”, I mean “ask them for help in meeting people”. If cold approaches is your bag, one of your friends acting as your wingman or wingwoman could help you feel more confident while you’re out and about. Your female friends can be especially valuable here; having attractive women in your life who clearly like you and enjoy spending time with you is a form of social proof. It tells others that you’re vouched for as a good guy, who’s got a lot going for him. That can make a pretty significant difference.

Similarly, ask your friends to set you up with an introduction or point you towards someone they know. Even in the age of ubiquitous dating apps for every possible permutation of relationships, most people meet their partners through shared activities and mutual friends. So tell your friends that you’re on the market and to let you know if they know someone they think you’d click with. Maybe they could provide you with a direct introduction. Maybe they could invite them along the next time you’re throwing a party or hosting an event of some kind. You’ll still have to do the heavy lifting yourself – there’s no skipping that part – but having a friend vouch for you goes a long way towards making that love connection.

Dating can be a confusing, even frustrating task at times. In those moments, it’s good to take a moment, take a breath and do a deep and impartial examination. Figure out what you’ve been doing that isn’t working for you, make adjustments and see where things take you. Before you know it, you’ll hit your stride and break through those sticking points.

Good luck.