Estimated reading time: 12 minutes
Hi Doc,
So the last few months I’ve been dedicating myself to dating.
I’ve come a long way from not being able to say hi to a girl, but flirting and asking for numbers. I’ve also been active on OLD and attending singles events when I can.
But even through my confidence is sky high, I’m not getting results apart from a few numbers. I haven’t even gone on a date with a girl yet, much less had sex.
I know I’m attractive enough. I know I’m confident. I know I’m charismatic. But it’s just not translating into results.
Recently I’ve actually had to stop pursuing dating so hard because I just felt so burnt out. I’ve been scouring the internet to find advice for blokes in my position. But all of these just contain stuff that I’ve already internalized and mastered.
I’m still talking to girls at work, and I feel less pressure now that I’m not aggressively pursuing something. But it dosen’t change the fact that I’m still utterly lost when it comes to it.
I’m at my wits end trying to figure out what exactly my problem is; And frankly I’m sick of losing sleep scrolling Reddit and google searches trying to find a solution.
So my question is:
What issues am I facing in dating if I’ve already built confidence?
Desirous of Dating Debugging
First of all, D3, you should be proud of the work you’ve been putting in and the progress you’ve made. This is one of the reasons why I talk about how you should focus more on progress and milestones, rather than on the final outcome or the ultimate goal. I understand that you’re frustrated because you aren’t getting the results you were hoping for yet, but you have made significant improvements and changes. That’s no small thing, and I think you’re not giving yourself credit for it.
I also think that you should give yourself credit for recognizing that you’re starting to burn out and need to take a break for a moment. I know that it can feel like giving up or admitting weakness, but putting things on pause while you take a mental health break is a good thing. Paying attention to your overall emotional state and being aware of when you feel the frustration rising to troubling levels is good, not just for your emotional health, but for maintaining the progress you’ve been making.
It’s incredibly easy to fall into the trap of going “on tilt” – a state of where you let your frustration and disappointment push you into making increasingly wild, irrational and often overly aggressive plays in order to try to brute force a win. Someone constantly going all-in on every hand, for example, is someone who’s no longer playing with care or strategy and is just trying to make a win happen at any cost. At this point, it’s become about trying to soothe a wounded ego and even a win won’t make up for the amount of money lost in the process.
So it is with dating; when you feel like you’re putting in all the effort and getting nothing for your work, it’s easy to end up in a headspace where you’re no longer trying to find a partner so much as just make the frustration go away.
The problem is that when you get into this headspace, it’s very hard to actually think rationally and pick up on where you might be making mistakes. A lot of people will pick up bad habits or adopt poor strategies for trying to get women to talk to them or pay attention. Many fall victim to the slapdick grievance peddlers’ snake-oil solutions, which inevitably only serve to make them angrier, more frustrated and more willing to throw good money after bad. Still others will stop looking for a partner and instead start trying to fill a hole marked “girlfriend”, not caring about how poor of a fit that person may be. Worse, some end up with a toxic relationship with someone they would never have dated in other circumstances.
Taking a break, focusing your time and attention on other things that actually feed your soul and bring you contentment and meaning is invaluable at times like these. Much like taking a break when you’re about to snap your Xbox controller in frustration, stepping back and just not thinking about it for a while gives you the bandwidth to think clearly again and figure out what may be going wrong.
Case in point: you’ve got the confidence locked down, but so far, this isn’t turning into dates. This one’s fairly easy: confidence isn’t the magic attraction formula, and it’s not going to get you dates by itself.
Now that’s not to say that confidence doesn’t matter. It does. Confidence is important when it comes to dating, on many levels. Being confident in yourself makes it easier to meet people, strike up conversations, build connections and ask someone out on a date. Similarly, it’s a significant part of charisma – that sense of certainty, purpose and faith in oneself is incredibly appealing. But confidence on its own isn’t going to be what makes someone fall for you.
Confidence is tricky, in part because it’s an aspect where its presence isn’t going to guarantee success, but its lack makes failure much more likely. It may help to see this as a trait that lets you roll with advantage (in D&D terms: rolling two twenty-sided dice and choosing the higher of the two rolls) while the lack sees you rolling with disadvantage (where you choose the lower of the two).
Some of this is because of what a lack of confidence says about you (the general “you”, not you specifically, D3) – if you don’t believe in your own worth, value and capability, why should anyone else? There’s a reason why nobody advertises a product as being “not great, but give it a try anyway,” after all. That’s going to put people off.
However, that lack of confidence also carries a message about what a relationship with you would be like. Not only does it tell them that you don’t see that you’re worth their time, but that a relationship with you may well mean that they’re going to spend a lot of it propping you up. Most people are struggling enough managing their own emotions and feelings of self-worth; they aren’t going to want to have to manage a relative stranger’s as well. Especially if that stranger is correct and doesn’t bring anything to the table in that relationship.
Is it possible that someone may overlook this? Sure. But its stacking the odds against you and making it far more likely that things won’t go your way.
Here’s the thing: attraction is a holistic experience. It’s about the entire person – the sum totality of who they are, rather than any disparate aspect of them. Someone can have the cheekbones of an angel and the abs of a Greek statue, but still be utterly repulsive to others because of their attitude and personality. On the other hand, someone who looks like a Deep One dipped in nicotine can be absurdly charismatic and attractive because of their wit, passion, talent and gift of gab. Does that mean that one’s physical looks don’t matter? No, they do… but they aren’t the alpha and omega of dating. They’re just a part of what someone may or may not find appealing about you.
But it’s important to note that attraction isn’t a passive experience, it’s active. That is: it’s not just about someone standing around being hot and then everyone throws their underwear at them. Attraction is in what someone does as much as in how they look – how they carry themselves, how they interact with others and, critically, how they make people feel. Tom Cruise is famously charismatic in no small part because of how he makes everyone, no matter who, feel like the most fascinating person in the world. Jack Black and Matt Berry are talented, expressive, creative and funny – they make people feel good through their humor. Will Smith and Chris Evans both radiate personal warmth and approval, helping others feel seen and validated.
A lot of the effort that goes into being attractive and building attraction can also go unnoticed. Many of the common signs that a woman is attracted to you – laughing harder at your jokes than they may warrant, being very complimentary, asking questions to get to know you better – are about endearing themselves to the person they’re into. It may not be as immediately obvious as flirty banter or the effort they’ve put into their style and presentation, but it’s still done with an aim of how it makes the other person feel. The sense of “this person thinks I’m funny!” or “they really value my opinion!” makes the recipient feel good, which makes them want to prioritize the time they spend with this person, rather than time spent with someone else.
So I think it’s going to be important for you to think about the interactions you’re having with people and the kinds of emotions you’re working on bringing out in them. Being mindful of the ways you talk to them, the things you talk about, showing them that you’re interested in them as people and want to know more about their interests and opinions are all important. You want them to feel that interpersonal warmth, to feel validated and appreciated when they talk to you. The more they enjoy talking to you, the more’re they’re going to want to spend time with you. The more fun you help them have, the more you increase the odds that attraction is going to grow.
Now this is a balancing act, and it’s easy to tilt too far from “being fun to talk to” to “putting on a show”. I suspect that’s another part of the problem you’re having. You even say that you’re still talking to women at work, but now without the pressure of trying to get results. That’s important, and I think you should really pay attention to the difference in how that feels versus the way you were talking to women you were ostensibly trying to pick up. I rather suspect the difference is palpable and noticeable. Even if it isn’t to you, it definitely was to those women.
When you get hung up on outcomes – getting someone’s number, getting a date, getting laid – you lose focus on the fact that you’re supposed to be enjoying yourself and getting to know the other person. You end up trying to do things “the right way” and get a specific result, instead of being in the moment and just vibing with another person. This changes your body language, your vocal inflection, even just the overall vibe of the interaction… and not for the better.
I still remember talking to an attractive woman at a bar who interrupted me and said “Are you practicing a bit right now?”, prompting me to crumble to dust before her eyes and blow away. But she was right; I was so focused on being “fun” and “entertaining” that it came across like I was workshopping my tight 5, not having a fun, flirty conversation. That tends to come off as really impersonal and off-putting; it doesn’t feel like you’re talking to someone or being a person. At the time, I, like you, had been putting a lot of pressure on myself to perform – with an emphasis on “performing”. Once I learned to dial back my expectations and just enjoy talking to people, things proceeded much more smoothly and successfully.
This is why, when you’re ready to give dating another go, it’s going to be better to let go of the outcome and just focus on having enjoyable conversations with interesting strangers. Yes, I realize that it sounds entirely contradictory to pursue success by letting go of the desire to succeed, but that’s precisely how you avoid going on tilt. If you can learn to value each conversation and interaction for its own sake, instead of pressuring yourself to get a particular result, you let go of the performance of it all and instead can just be in the moment. It means that you won’t be in your own head and instead can just focus on getting to know this person and figuring out what’s interesting or cool about them. That will make you much more charismatic and attractive than being yet another dude hitting on them on a Friday night.
I’d also point out that being able to just enjoy the moment for what it is, rather than trying to get a date or avoiding rejection will help increase that sense of attractive confidence and charisma that you’ve been working on.
The last thing I will tell you is that I can guarantee that you’re moving too fast – that is, you’re trying to get immediate results instead of letting things breathe and grow. If you’re defining success as getting a number or a date (or a sloppy make out session or…) on the same day that you’ve met someone… well, there’s a big part of your problem.
A lot of guys, when they start really focusing on dating, get hung up on getting results and getting them quickly. Part of the reason why pick-up artistry fails most men is because they’re trying to convince a relative stranger to be interested in starting a romantic or sexual relationship with them after having known them for maybe 20 minutes. They’re often expecting meeting women and dating to look like Ryan Gosling picking up various women in Crazy, Stupid, Love or John Hamm bringing home women he just met in Mad Men, and then getting increasingly upset when it doesn’t work that way for them.
Well, a big reason for this is that this just isn’t how the vast majority of people start a relationship. It’s very rare for someone to start dating someone they just met that day, and even less so from a cold approach at a bar or club. Most of the time, we date people we’ve met in lower-key circumstances, and usually have gotten to know over time. When we meet our partners in person, it’s almost always in the context of mutual friends or shared interests or activities and often having met multiple times.
That last part is crucial. Propinquity – the tendency to form connections with the people we see and interact with the most often – is one of the most underrated and overlooked aspects of attraction. The more we’re exposed to something or someone, the more likely we are to grow an attachment to it. The more you hear a commercial jingle, the more likely you are to buy the product. The more you hear a song, the greater the odds that you to start to like it.
So it is with people. Part of the reason why we tend to develop crushes on classmates or co-workers is because we interact with them regularly. Not only does that give us a chance to get to know them, but it also triggers the propinquity effect, which builds greater fondness and interest.
If you want to have more success, it’s going to help to slow your roll and take the pressure off yourself to get results. Seeing them often and having good conversations with them will get you a lot farther in terms of getting numbers and dates than trying to speed run the process and get a date before the bartender announces last call and the lights pop on.
Good luck.
