Is It Time For Me To Quit Trying to Date?

Estimated reading time: 13 minutes

Hi Doc,

To really oversimplify my background: early 30s, kissless virgin, only been on 4 dates, one being a second date.

So, I had been curious about a coworker for about a year, and finally realized she wasn’t interested in me. I suggested several times meeting up, and she never said no but was non-committal. I let those answers and the ambiguity be the basis to keep hoping there was something. A bit after accepting that truth, she expressed concern to the company HR when she found out I might be moved to her section.

I don’t want to make it out like she was deliberately hurting me, she was perfectly right to say what she felt (even though I had moved on by then), but it was an extremely painful experience. I feel like every guy I’ve hated for being too pushy with women.

I have no plans to look for a girlfriend among coworkers again (and may turn down going out if the most improbable happens and someone asks me). I guess what I’m feeling now is just that getting a talking to by my company just really reinforced my negative feelings about being dating and relationships. I just feel really unwanted and no matter how attracted I am, and however much I fit what a woman says she wants, I’m not what she’s looking for.

I can honestly say that outside of a few people that fizzled within one date (and I suspect those were more due to sympathy), I have never known a woman to be attracted to me.

I’m trying to do more things I enjoy, and have had success. I have trouble with energy outside of work and finding motivation (I suspect some symptoms of ADHD) and my improvement is not linear. I guess I’m just struggling to find a reason to believe I can find someone. I’ll keep improving my life, but I don’t know if I should keep trying to find a relationship. It’s getting really painful to keep trying.

Tired and Lonely

OK TAL, I’m going to tell you something you already know: just because you think you fit what someone wants in a partner doesn’t mean that you actually fit. 

We’ll leave aside the question of “is that what they want or what they think they’re supposed to want” and focus on the list of traits.

If you’re a regular reader, then I’m sure you’ve seen me talk about how people in general and women in particular don’t date someone based on a list of criteria. Even when it’s less “he has the six sixes” and more about “I want to date a guy who’s into subtitled movies, picnics in the park and likes to write stories about shapes in the clouds”, that doesn’t mean that she’s automatically going to fall for someone who happens to tick those boxes on her checklist. There’s always going to be that unspoken – but understood – addendum: “…who I’m attracted to”. 

I’m sure that, if you look at your own life, you can recognize plenty of things that in theory should be precisely your shit. It could be a podcast, a book series, a movie, a restaurant, even a person. And yet, for whatever reason, it just doesn’t work for you. The movie doesn’t make you laugh or thrill you, the book or podcast doesn’t engage you and the person just leaves you cold. Even though, objectively, it (or they) have all the things you like.

Chemistry and attraction are always going to be the secret sauce to a relationship, even ones that seem perfect on paper. Without those, then nothing is going to happen.

Now I bring this up, not to reinforce the “women don’t like me” part and more to emphasize that you’re focusing too much on the “but I’m exactly what they say they want”  end and missing the forest for the trees. And if I’m being honest? I think part of it is because you’ve reached the point of looking for A Girlfriend and you’re just trying to find someone – anyone – to fill the role. 

There’re a lot of reasons why that’s a bad idea, chief among them the fact that women as a rule don’t appreciate feeling like they’re just the one who said “yes” this time. But more specifically for your situation is that it leads to circumstances where you don’t want to take a “not interested” at face value. When you hit that particular event horizon, the person starts to matter less than what they represent. A lot of times, what they represent is “your last chance at avoiding a lifetime of loneliness”, and when you hit that stage, it becomes very easy to choose to interpret a “soft no” as a “so you’re saying there’s a chance.” 

Just as importantly… when you reach that point, you’re often looking for a girlfriend, less because you have a deep and abiding affection for this specific person and more that you’re trying to prove something to yourself. And that’s where shit gets difficult.

Here’s the thing, TAL: dating means courting rejection. You’re going to get rejected when you’re trying to find a date, because not everyone is going to be a good match for you, and even people who might be a good match may not be in a place where they’re a match for you right now. And unfortunately, there really isn’t a way to know whether or not someone wants to date you without just asking them and making yourself vulnerable. 

But you have to be ready to not just take rejection, but to take it for what it is, not what you think it says about you. If you start taking the wrong lessons, then all you do is set yourself down a path that’s going to make things worse.

Let’s take the example from your letter. The lesson to take away from this isn’t “I have become the pushy asshole I hate, I should never try again”. The lesson you should learn is “if you don’t get a ‘yes’, then take that as a ‘no’ and move on.” If you’d taken that noncommittal response as the polite “no” that she intended it to be, then this wouldn’t be an issue. It would still suck, because nobody likes being rejected, but it doesn’t mean that you need to turn down any and all possibilities just because you work for the same company or whatever. 

What you’ve done is taken this one instance – one that, to be sure, was an error in judgement on your part – and turned it into yet another method of hammering yourself in the nuts.  And that’s the real problem here.

“But Doc,” I hear you cry. “It’s not just the one time, it’s all the times.” And yes, we will and should acknowledge that you’re having a hard time meeting someone. But the answer to that isn’t “well clearly nobody will ever love you and you should just give up”. The answer is “OK, so if that’s not working, let’s figure out why and how we can change that.” Because, yes, it can be changed. If you want different results, you have to do things differently. 

The first thing to do is to start changing the way you talk about or to yourself.  There is a difference between “no woman has ever been attracted to me” and “I don’t know that a woman has been attracted to me”. That’s an important distinction because… well, you don’t. All you know is that the women you’ve asked out haven’t been into you; that’s not the same thing. One is definitional – you are defining yourself as being unloveable. The other is informational: you aren’t aware of people who might have been attracted to you, but that doesn’t meant that they don’t (or can’t) exist.

I’m sure you haven’t been attracted to every woman you see, nor have you approached every woman you’re attracted to. So if it’s possible that you may have been into someone but did nothing about it… what makes you think that this couldn’t be true for women? You don’t need to be all Pollyanna and say “many people are madly in love with me, I just don’t know it”, but acknowledging that shit sucks right now doesn’t mean that shit’s going to suck forever is important.

Similarly, deciding that women only went on dates with you out of pity is not only not likely to be correct, but not helpful. Again: all that is just another case of your jerkbrain crafting a narrative to use to hit yourself in the nuts with. Saying that to yourself is just another way to run yourself down, not something that could lead to finding shit to improve upon. All it does is sap your willpower and your drive to improve, just overloading yourself with more negativity and self-recrimination which – again – isn’t helpful. 

And that “not helpful” part includes things like “well, I’m clearly a horrible person and should never talk to women again” when you’ve made a mistake. The attitude you want to take is “Ok, I messed up here, how can I do better so I don’t mess up again?” 

Just, y’know, without falling back to “just decide to be alone forever and give up ever wanting things”. Because that’s not a reasonable reaction, that’s just throwing your hands up and saying “nobody loves me, everybody hates me, I’m going to the garden to eat worms”. 

Do you want to do better? Do you want to have greater emotional strength and energy, so that those set backs don’t destroy you? Then stop running yourself down and start incorporating more positive self-talk into your life. Tell yourself “ok, that didn’t work, but I’ll learn and do better next time”. Or “OK, I’m not putting the best version of myself out there, I’m going to fix that”. Acknowledge the setback, but also focus on the temporary nature of it, and focus on the fact that you can and will do better.

So, nobody has shown interest in you? OK… well, right now, it doesn’t seem like you like you very much either. So maybe you need to fix that, first. Nobody is going to want to date a guy whose whole outlook is “It’s ok if you don’t want to date me; I wouldn’t want to date me, either”. 

There’re a lot of reasons why I say “the first love of your life should be the love of your life”. That is, do you like who you are? Do you like your life? Do you have a life that other people could share with you and be happy? Because right now it sounds like the answer is “no” and you’re hoping that a girlfriend will be the solution to it. Except – and I meant his sincerely – then what? What, precisely will a girlfriend bring that will make the rest better? Because I can tell you from personal experience that just having A Girlfriend won’t change anything for you. It won’t make you a better person, it won’t make your life better or more engaging or more interesting and it definitely won’t cure your depression or lack of motivation or anything else. All the good things that you – or many others – hope a girlfriend will bring to them are things you have to bring yourself instead. 

Want a better, more engaging social life? That’s on you; a girlfriend won’t fix that for you. Want to feel better about yourself as a person? That, too, has to come from within. A girlfriend right now won’t make you feel wanted or desired; it’ll leave you worrying that she’s about to dump you at any moment because you can’t accept your own worth. Without that baseline of self-worth and internal validation, all a girlfriend will be is a rug over a gaping pit… and anything you put on that rug’s just gonna fall straight in.

I realize this sounds like I’m minimizing your pain and your frustration. I promise you: I have been there, I have done that and I printed the t-shirt. I’m telling you what you need to know. And what you need to know is that first you have to be someone you would want to date. That doesn’t mean “go to the gym until you’re a sculpted Adonis”, it doesn’t mean “be smoother than Lando Calrissian on satin sheets with a magnum of Colt .45 on ice”, and it doesn’t mean “change everything about yourself until you’re a carbon copy of Pete Davidson” or whatever. It means that you have to build the kind of life you think you would have if you had a girlfriend. That includes things like “talking to a therapist” and “decouple your sense of self-worth from your relationships” because honestly? It sounds like you’re dealing with depression on top of ADHD. 

Am I telling you that you need to go change everything about yourself? No… but I am saying that you’re clearly not happy with who you are at the moment. So maybe it’s worth looking at some of those aspects of yourself and saying “ok, what parts am I most dissatisfied with and how do I change that?” 

(Besides being single, that is). 

And yes, change is possible. But it takes work, it takes time and it’s not going to deliver instantaneous results. And if you make changes that are entirely about attracting the sort of women you think you’re into rather than making changes that are genuine and organic to who you are as a person, then it’s only going to make things worse. You don’t want to be someone else’s idea of a desirable man, you want to be the best version of yourself. And sometimes becoming the best version of yourself means letting go of things that you have decided are just Who You Are, not because they’re involate or unchangeable, but because you gave up on trying to fix things. It’s very easy to say “welp, that’s just who I am, I’m Johnny No-Maidens”, instead of saying “Ok, I said that I can’t be someone who talks to strangers, but what if I’m wrong?” or “I’m not someone who can dress like a cool person” or otherwise be the person you want to be.

Which is not to say that everything is changeable or that you can become the EXACT person you think you should be. You will encounter things that can’t be changed or aren’t going to be congruent with who you are. But that just means you shift to “ok, so how do I adjust and work around this?” instead of throwing your hands up and saying “it’s too much/too late/impossible” and giving up.

And speaking of giving up: one thing to consider is that you’re tired and you’re frustrated, and that’s making things harder for you. You’re stuck on the same part of the boss fight and not only can you not beat the boss, but you’re getting so worked up that you can’t even get to the same stage of the boss fight; now you’re getting bodied before you even take down their first life bar.

When you hit this point, the answer isn’t “do the same thing BUT HARDER”, it’s to put down the controller and walk away for a bit. Right now, yes, you should stop trying to date. You’re getting frustrated, you’re getting upset, you’re blaming yourself and it’s making everything worse. Give yourself permission to stop trying and just focus on yourself for now. All those things I told you to do? You should focus on those, not on trying to beat the boss. Taking the pressure to get A Girlfriend off the table will free up resources to just be good to yourself for a while. You will close out the extraneous mental apps that are sucking up all your available bandwidth and you can take that and apply it to making a better You, instead. The game – or dating, in this case – will still be there when you’re ready to get back to it. Except this time, you’ll be rested, relaxed and ready to give Slave Knight Gael a wedgie… metaphorically speaking.

Take a hiatus from trying to date, even from looking. Think of it as an extended vacation while you get back into fighting shape. Go through my site, use the resources I provide, possibly book a coaching session or two and work on yourself. Not only will you be ready to start looking again, I’m willing to bet that you won’t have to. Take care of yourself the right way, and you’ll find that amazing opportunities will just seem to fall into your lap like magic. Except it won’t be magic. It’ll just be the side-effects of your hard work and progress, things that will happen organically because you created the circumstances for them to occur.

You’ll be ok. I promise.

All will be well.