I have never had much luck dating. Whenever I ask anyone about this, they tell me I need to focus on myself. I need to find interests, work out, work on other goals. Then I do all of that… but still no luck. Then I’m told I need to do them for their own sake, not for women. So then I do that, still no luck. This feels downright Sisyphean, just constant shifting of the goalposts, still having no idea how to approach without being creepy, how to flirt, how to properly attract women.
When do these goalposts stop moving? When can I actually learn the skills I need to date? No matter how much I can lift, no matter how long and fast I can swim, no matter how many hobbies I pick up, that still won’t teach me how to properly approach, be not creepy, and flirt.
When does this happen that I finally learn?
Stuck In First Gear
So, this is something that comes up a LOT: the question of “when will I finally be good enough to date? How much ‘self improvement’ do I have to do?”
This is an understandable frustration; as you say SIFG, it can feel like you’re Sisyphus and his good buddy Bouldie, trying to make it to the top of the hill every time. It seems like every time you turn around, there’s some other thing that you’re supposed to do, that you were supposed to do instead, or that you’re just doing wrong and now you need to do it like this.
However, the chief cause of this frustration is that a lot of folks go about trying to get better at dating in an incredibly piecemeal fashion. That is: more often than not, what they’re doing is looking for that One Weird Trick that will turn their entire life around and make everything easy like Sunday morning. And, in fairness: there’re a lot of folks whose entire business model is predicated on selling the idea of “Do This ONE THING And Women Will Fall At Your Feet”, as well as the number of folks who will tell you “well… just be yourself,” as though that solved anything.
It never does. And — again — this is understandably frustrating. But the truth is that the people who struggle most with feeling like they’re stuck in a Red Queen’s Race — running as fast as they can and going nowhere — are almost going about things the wrong way. This starts with asking the wrong questions and, as a result, addressing the wrong issues.
Case in point: your question, SIFG. It sounds like you’ve gone into the piecemeal, “a little from column a, two from column b, one from column c” approach towards trying to solve your dating issues. The reason why this rarely works out is that the people who take this approach are treating dating as something separate from their every day lives. In reality, dating is a holistic practice; it’s not something walled off from the rest of you, it’s part of the sum totality of who you are as a person. If you’re having issues with dating, then this almost always ties into your life as a whole, rather than needing a magic bullet to fix the issue. To solve things, you want to figure out exactly where the disconnect is happening so that you can zero in on causes and solutions.
This is much harder to accomplish when you’re jumping all over the place and putting emphasis on different aspects of your life; doubly so when you don’t get why doing X or Y is important or where you should focus your attention. Take the way you describe things in your letter. You say you’re doing all of these things to get better at dating… but you don’t say where things are falling down or how, and that’s important. Are you, for example, having a hard time talking to people and carrying on conversations? Do you struggle with social skills and ways of connecting with people on an intimate level? Or are you having issues with self-esteem that make it hard for you to express yourself or show interest in the people you want to date? What are your goals for, say, swimming, lifting or picking up hobbies? Are you doing these because you’re hoping that they’re going to make you more attractive? Because you’re hoping that they’ll bring you in contact with people with similar interests and make it easier to meet women who you’re likely to be compatible with? Or are you hoping that these will make you attractive enough that women will do the heavy lifting for you?
All of these are entirely different issues, and ones that have entirely different fixes; bouncing around just means that you not only never fully develop in the directions that will help, but often result in your trying to apply them incorrectly.
Let’s take “work on yourself, find interests and hobbies for yourself”, for example, especially with the seeming conflict between “do this to meet women” and “do this for yourself”. The reason why folks will tell you to do X for yourself rather than to meet women is because a lot of dudes will pick up hobbies or dress in a certain way or — I shit you not — pick careers because they think that it will make them more attractive to women. The problem is that this means you’re not being authentic; you’re doing stuff that doesn’t actually speak to you, that you may actively dislike, in order to meet women. And while doing this could, theoretically, help you connect with women, it won’t actually lead to anything. Not only will it mean that you’re meeting people who you’re not compatible with, but that inauthenticity will bleed through. It’s really easy, for example, to tell the folks in a hobby space who aren’t there because they love the hobby. It doesn’t do you any good to pick up, say, swing dancing, if you don’t actually like dancing. Is it a valuable skill to have? Sure. Does it open opportunities for you? Absolutely. But if social dancing isn’t your thing — or worse, something that acts like 30 grit sandpaper to your nerves — then you’re spending a lot of time doing something you hate in order to meet people… who like the thing you hate.
I mean, I spent a lot of time trying to meet people in bars and clubs that I disliked before I had my long dark tea time of the soul and realized how much all of this had fucked with my head.
However, the benefit of picking up hobbies and skills for yourself, things that actually speak to you and that you enjoy, is that they help you be a more interesting, well-rounded person who lives an interesting and fulfilling life. A person who is happy with his life, who has things going for him besides “work/sleep/repeat”, is an attractive potential partner because he’s got his shit together. He has passion and joy in his life, he has ambitions and goals, drives that go beyond getting by. That means life with him will be more fun and fulfilling, which is a vital part of a relationship’s long-term success. And choosing things that authentically speak to you make it easier to meet women who share those interests, women who are actually right for you.
So if you enjoy exercise, lifting weights and swimming then by all means continue to doing all of that! They’re beneficial in and of themselves and they improve your life because you enjoy them. But what they don’t do is act like a magic girlfriend magnet… which is something a lot of folks expect. Even if you devote time to becoming an incredible salsa dancer or whatever, you still have to put in the work to meet women, connect with them and take them out on dates. They aren’t just going to just show up on your front porch one day.
By that same token, just because these can all make you a better match for folks, that doesn’t help if you’re not able to take advantage of opportunities when they arise… or, for that matter, if you can’t recognize them when you come across them. Yes, there’s a lot of luck involved in meeting women, but luck really is the byproduct of preparation and opportunity coming together. All of the opportunities in the world don’t help if you aren’t in any position to pursue them. Lots of folks seem like they’re perfect on paper but just can never make the whole “attraction” thing happen because their skill sets suck. I’ve worked with hot, rich guys who can’t bring themselves to just open their mouthes and talk to people… and the truth is that nobody is going to be so invested in you that they’ll do all the work. The hottest of the hot may get attention, even people willing to make the first move… but there needs to be reciprocity. Even the women who’re willing to make the first move are going to get bored or frustrated and move on if the person they’re moving on doesn’t respond, doesn’t show interest or proves to be ten pounds of shit in a five pound sack.
(Ask any of your friends who sleep with men how many hot dudes they know that made themselves unfuckable by opening their mouths…)
You say that you don’t know how to approach women or flirt with them… and, well, there’s your problem. No amount of lifting or “cool” hobbies are going to substitute for actually opening your mouth and making the words go. That’s back to the issue of looking for your car keys under the streetlight because you can see better there. If you’re having issues with knowing how to read folks or how to flirt or even just to be a good conversationalist, then that is what you should be focusing on. And if I’m being honest… well, if that’s your issue, it sounds like been getting in the way of asking for help too because all of what you described isn’t gonna help.
So in this case, it sounds like you have an issue of using your words and actually asking for what you need help with. If you’re just telling people “I’m having a hard time dating” or “I don’t know how to meet women”, then you’re going to make it a lot harder to get the information you need. You’re setting yourself up to get a lot of generic or unhelpful advice.
Now let’s say that this isn’t just an issue of needing to get better at talking to women or knowing how to flirt. Let’s say it really is an overall issue of “needing to start from scratch” and you aren’t sure what needs to be worked on.
This is where it becomes important to start getting organized and methodical. If you want to improve at something — or a lot of things — then you want to make a plan so that you aren’t just bouncing from topic to topic, hobby to hobby or skill to skill. That’s not even a good way to be a jack of all trades, just a lot of half-developed, not terribly helpful skillsets and abandoned hobbies.
Drafting a plan means figuring out what needs work, what your end goals are and how to best achieve those goals. Sometimes it’s easy to see how to get from A to Z. Other times you need to start at Z and work backwards; what would be the step before Z? What would you get you to that step? And then the step before that one. Now, this can be tricky, especially because a lot of people have incredibly unrealistic ideas about what it takes to be attractive to women and that can lead you down some dead-ends.
However, sometimes the key is to think outside of the box; occasionally the key to reaching your goals means that you bankshot off something that seems like it might not be directly related. One of the tricks that helps people get better at flirting isn’t related to flirting at all: it’s to study improvisation. By taking some improv classes, you learn how to get out of your own head, to quit trying to come up with the “perfect” line or the cleverest quip and to just be in the moment. You learn how to be in the moment with the person you’re talking to, to focus on them and to be a collaborative conversational partner, rather than anxiously studying every possible micro-expression in order to gauge how you’re doing. Will you also get funnier? Possibly… but that’s not the immediate point. It’s to learn how best to get out of your own way and enjoy talking to someone for its own sake, rather than hoping to hit all the attraction switches and prove that you have sufficient “sexual market value”, or whatever the fuck the term is this week, to a relative stranger.
The key to improving quickly and to not overwhelming yourself is to find ways to incorporate practicing these skills in your everyday life. This is, for example, why I push practicing having brief, low-investment conversations in places like waiting in line for coffee. Not only does this help you find more opportunities to practice and develop your social skills, but it also turns “talking to strangers” from something you have to think about into muscle memory. This means that when it actually counts — such as having an opening to talk to your cute classmate while you’re heading to your Victorian Lit seminar — you don’t have to push yourself through approach anxiety or force yourself to make an approach. All that practice means that talking to people is just something you do, so it’s much easier to strike up a conversation and see where it goes. And if you’re comfortable starting a conversation with someone, it doesn’t take much more to say “I’m really enjoying talking to you; would you like to grab coffee at the Student Union?”
It’s also worth noting how many of these skills build on one another. Folks freak out about flirting because they are too in their own heads. Learning how to get out of your head makes it easier to feel more confident. Feeling more confident means that you take more opportunities when they present themselves. Taking advantage of those opportunities gives you changes to flirt. Flirting leads to dates, dates lead to relationships. You cultivate these skills that lead you to your goal because you figured out how to shut up your jerk brain and just be in the moment.
So it’s not that the goalposts keep moving, SIFG, it’s that you need a little more organization, you need to ask the right questions and focus your attention on the right areas for the right reasons.
Now, sometimes it really does come down to “don’t know where to start” or “don’t know what I need to work on.” In those cases, that is when it’s time to get a little outside help. However — as I’m sure you’ve seen — getting help is easier said than done. Your friends, as well meaning as they may be, may not be able to help. Not because they don’t want to but because they don’t know how. Part of why people keep defaulting to anodyne, generic advice like “just be yourself” is because while they want to help you out, they may not have anything concrete to offer but feel the need to say something.
But that’s where I come in. Between my books, podcasts and videos, upcoming courses and an extensive archive, I’ve almost certainly got you covered. If you need something more personalized, I have private coaching options available.
I get it. It can feel maddening and frustrating and every time you turn around it seems like there’s something else that people are saying you need to do. But if you slow down, take a deep breath and focus on what, precisely, that you’re struggling with, you can find your way through to social and romantic success.
You’ve got this.