Estimated reading time: 19 minutes
Hey Doc,
I’m sure you’ve touched on this before, but I’m really struggling with figuring out what I’d want in a relationship. A bit of backstory… I’ve written you before and you replied: “How to stop being bitter about women”. I was EXTREMELY angry back then, obviously. While I didn’t agree with everything you said, I have made some progress towards being better than I was then. I’ve seen some success in the recent months, and I’ve been dating a few women. My issue now is that I really don’t know what I want. You said it perfectly: “If you aren’t sure what a romantic partner would bring to your life that isn’t just about being a trophy that says You Won Manhood, then you need to sit with that question and really interrogate it.”
I get a bunch of matches on dating apps, and I get a few numbers in person, which have led to some dates here and there. I go out with these women and they’re… fine. I’m not really excited about them at all, I’m not really that interested in them and I don’t really want to text them or pursue them. Again, there is absolutely nothing wrong with them at all, they’ve all been lovely women. The girl that I’ve been seeing recently is very easy to talk to and has good energy, but she lives over an hour away and I’m not really physically attracted to her. Another woman I went out with was absolutely gorgeous, but conversation was like pulling teeth and so immensely boring.
In my gut, I feel like I should be over the moon about these women, especially the one I’m seeing now, but I’m not. I know it’s shallow, but I’m just not physically attracted to her at all. I know for a fact my standards for looks are way, way too high. I’m a good-looking guy, I work out and I’m taller than average, but my standards are far above my level of attractiveness. I really want to be happy with a woman that doesn’t meet those standards, but I haven’t been able to so far. Even if I were to get with a woman that does, I don’t even know if that would make me happy. If I’m being honest with myself, it’s about validation from others. I want others to see me with an attractive woman. I just want the trophy to show off to everyone else. At the same time, there is still a hint of that bitterness in me. I’ve put in an immense amount of work to get where I am today, internally and externally, and I want to be paid back for it. I understand this is wrong, and I’m more or less dehumanizing women with this thought process. I just took the girl I’m seeing now out to dinner. As she’s sitting across from me telling me a story all I could think was….”This is it? This is all I get.” I feel awful typing that out because she is a wonderful person and deserves someone who actually values her and will make her happy, and that isn’t me.
While I’ve seen more success recently, the opportunities are still hard to come by in abundance, so I don’t really think that I can figure out what I’m looking for by dating multiple women. I’m turning 30 soon and I feel like the clock is ticking….my parents are getting older and want grandkids, all my cousins are getting married and I’m tired of my aunts and uncles asking when it’s my turn. My best friend is getting married in October, and I’m the best man. When he asked me, I actually felt awful. Not that he asked me, but that I probably won’t be able to ask him to be best man in mine. I’m just not sure what to do or where to go at this point.
– Better, but Still a Bit Dejected
It’s good that you know your chief stumbling block is that you’re still thinking of this in terms of external validation, BSBD, because that tells you a lot about what you’re doing wrong. Now the key is to start unpacking the why of it and how you’re going to move past it.
There’re a few places where you should be digging in, starting with the fact that you’re looking at your self-improvement as an “investment” that you’re trying to get a “return” on. This right here is a significant part of the problem. I realize it sounds a little absurd to say “it was capitalism all along”, but… well, it basically is. You’re seeing this as though the only reason for any sort of self-improvement is the external reward that you get, instead of recognizing that the reward are the results of the improvements.
Exercise is a great example: getting fit can lead to aesthetic improvement, but the ultimate reward is… greater physical fitness. Your body moves better and more effectively, you feel more energized, your concentration and mood are better, your overall health and sense of well-being improve. Having a goal that you’re pursuing – running your first marathon, achieving a personal record lifting weights, being able to pass a physical for a demanding job like fireman or so on – can certainly motivate you and keep you going, but at the end of the day, the ultimate reward is a body that works better and all that means for your day-to-day existence.
The same goes for, say, learning how to play an instrument or how to paint or sing. The reward is in the improvement, in the learning, the growth, not the outcome. There’s a hell of a lot more satisfaction in accomplishing something you used to struggle with because you worked hard at it, instead of just hitting a button and POOF you have an outcome. You’re showing yourself what you’re capable of and what you can achieve.
Just as importantly though, is that when you’re doing it for yourself, not for the approval or judgement of others, nobody can take it away from you. When you’re focused on what others think, then what you have is precarious and fragile. Any person can wreck everything you’ve accomplished with a careless word or tossed-off criticism; suddenly the effort of months or years is brought down by a comment someone may never even remember making. But when it’s for you, when it’s about your journey for its own sake… it’s yours and yours alone, forever. You may never be Michelangelo, but nobody can take away the work you’ve put in or the progress you’ve made or everything you’ve learned.
And it’s important to consider just whose approval you’re trying to win or seek and why. What, exactly, are you hoping to prove by getting a “trophy” girlfriend and who are you proving it to? What is that going to do for you? How is that going to make your life meaningfully different in any way, shape or form? Congratulations, you’ve got a girlfriend who makes other people jealous… and so now what? What will that actually do for you? How will that change your life?
Here’s how: it won’t. You will have, at best, a momentary thrill. A flickering feeling of “yes!” And then doubt will set in. You won’t feel happy or secure in your relationship because hey, turns out your “trophy” isn’t an inanimate object, she’s a person, who has her own goals, dreams and ambitions – ones that I can all but guarantee don’t include “be a pretty object for other people’s consumption”. You’re going to be continually feeling the specter of doom hanging over you as you fear that you didn’t really improve, that this is all smoke and mirrors and trickery and it’s all going to come crashing down around you any moment. Worse, if your self-worth is entirely based around what other people think about your girlfriend… what’s going to happen when she’s not wearing Instagram-ready makeup at all times? When she’s not dolled up to the nines every single moment of every single day? When you both get older and time and gravity affect you the way it affects everyone? Are you going to hope you can trade her in like a used car and get a new one? Spend your entire relationship on a treadmill of maintenance to the point that you don’t have the time or energy to just enjoy your life?
And worse, what happens if your relationship doesn’t work out? If you two break up for any of the reasons why couples split? Now you’re not only dealing with the pain of a break up, but also the loss of your entire sense of value and self-worth.
The problem here is that you’re treating this like you’re in a competition that nobody else is aware of, performing for the pleasure of judges who don’t exist, for a score that nobody actually cares about. At most, you get temporary notice from strangers, many if not most of whom will be happy to shit all over your accomplishment and tell you why it doesn’t count. And that’s a toxic reason to do… well, pretty much anything.
Now let’s take a step back and consider the people you’re dating. Clearly, physical attraction and a sexual connection is going to be important for you in a relationship and that’s fine. Making physical attraction a priority is an entirely valid and legitimate choice. Nobody is going to seriously or sincerely tell you that you shouldn’t date people you’re not attracted to. It’s not going to do anyone any good; if anything, it’s going to cause harm to everyone involved.
However, I think it’s worth asking yourself if you’re not getting in your own way here. The “this is be best I can get?” you mention is important, because it ties right back into that return-on-investment view I mentioned earlier. You’re treating their interest in you as a judgment on you, that the fact that they like you and want to go on a date with you is somehow a measure of your worth as a person. It’s that sense of “well, I deserve better,” but why, exactly? What about you “deserves” a different, presumably superior person, and how do you make that judgment?
Alternately, is “the best I can get” about the fact that you’re on a date with someone you’re just not physically into, and you’re worried that you’re going to have to resign yourself to a lack of physical attraction if you want a relationship? In that case, then I think it’s worth asking yourself why you said “yes” in the first place. You are, after all, allowed to not go on dates with folks you’re not into. And seeing as you liked them well enough to match with them in the first place, then perhaps the question is “did you say yes because you’re afraid to turn down any opportunity?”
By that same token, is it possible that you’re talking yourself out of any interest because you feel like that invisible audience and imagined judges are shaking their heads at you? Are you not giving them a chance because you’re comparing them to the Playboy Playmate you think you’re supposed to be dating? When you’re not feeling it for them, whose voice(s) are you hearing that tell you that you’re not? Yours? Or someone else’s? Would you feel differently if you didn’t feel like you were being judged or “expected” to date a particular look or type? Would you be willing to give them a chance if you knew that nobody would give a damn and would approve regardless of whether they were someone else’s idea of hot or not?
While you’re considering that, I would also recommend that you stop giving such credence to your aunts and uncles who are asking “when it’s your turn”. They’re asking because they want you to be happy, and they think that they’re helping… but it ain’t helping. If anything, it’s making things worse, because it’s increasing that sense of pressure and sounds like the relentless tik-tik-tik of a clock. That’s contributing to the feeling that time’s running out when it isn’t.
Fortunately, it’s an easy problem to solve: you tell them to stop. The answer to the question is “when I meet someone who’s right for me,” and that’s all they need to hear. If they ask again, you can remind them that it’s been asked and answered, and that you’re not interested in discussing it further. If they continue to push, you can make it clear that you are living your life on your time and at your own pace. You will settle down when you find the person who’s right for you, not who’s right for them. If they remind you that your parents are getting older, you can tell them that every time they ask, you add another year for how long you’re going to wait… so maybe they should stop asking. You are allowed to have boundaries with family, after all, including family who are being pushy and intrusive.
But more than anything else, I think the best thing you can do for yourself is to work on killing the judge and audience in your head that’s telling you that you need to meet their approval. Like I’ve told people before, think of what you would do if you were living your life solely for your own satisfaction, your own enjoyment and contentment instead of living it for others. How would it be different if you knew, down to your bones, that nobody would ever know or care or judge you on all those criteria that you’re holding yourself against and you had total freedom to live your life as you chose? What would you do differently? Who would you be interested in?
I think, once you give yourself permission to focus on what you want, not what you’re “supposed” to want or what other people think, you’re going to have a much better time of it. By letting go of trying to live for other people’s approval – especially when it’s imagined approval – you free yourself to truly work on one of the most important relationships you can have: the one with yourself. Get to know yourself, what you truly want, free from the pressure of expectations and judgement and what would honestly make you happy.
Do that, and I think you’ll have a much better idea of what you want… and who.
Good luck.
Why is it that the women who seem most compatible with me in terms of age and life stage are also the ones who completely ignore my existence?
I’m a classic late bloomer romantically. As a teenager and young adult, I had essentially no success with women. We can speculate about the reasons, but it’s one of those questions I’ll probably never fully answer for myself. Fast forward into my twenties, and not much had changed. I was constantly surrounded by women in the 18–30 age range, yet I still had no luck romantically.
Now I’m in my thirties, and objectively my life is in a much better place. I’m doing well professionally, socially, and personally. I’ve also become a talented dancer over the last six years — genuinely out of passion, not as some elaborate strategy to pick up women — so I regularly spend time in female-dominated environments.
Still, nothing has really changed. I remain invisible to the women who, on paper, should be the most compatible with me.
What makes it confusing is that I’ve always connected with women more easily than with men. Most of my close friendships throughout life have been with women. In my twenties, many of my friendship groups were made up almost entirely of women, some single and some partnered. Now in my thirties, the women I naturally connect with tend to be older than me, already in relationships, have children, or are otherwise unavailable. At the same time, as I’ve grown older, I’ve occasionally noticed much younger women — late teens or early twenties — at least acknowledging my existence. This isn’t to say that I struggle to connect with people at a similar life stage to myself. For example, I regularly visit the home of a woman my own age to practice dance moves, and we get along exceptionally well. The difference is that situations like this are the exception rather than the norm, and they’ve always remained strictly platonic.
So, all of this leaves me with a strange conclusion: I can’t be entirely unattractive or off-putting to women, otherwise they wouldn’t consistently gravitate toward me socially or feel comfortable spending time with me one-on-one. Many of my female friends have openly wondered why I’m still single. One in particular regularly insists that I could get a date if I really wanted to. Yet despite this, the women who actually seem appropriate for me romantically never seem interested.
For example, when I attend dance events, I often have women laughing with me, asking me to dance, and clearly enjoying my company. They’ll usually make a point of sitting next to me, and I’ve even had a couple lean against me while we’re talking or rest on my shoulder. I’m naturally quite flirty, so I tend to make playful remarks, occasionally with a subtle sexual undertone, give compliments, and generally try to be pleasant and respectful to be around. I’m quite popular. Again, these women are all unavailable in some way.
In contrast, there are single women within my own age bracket who have been attending these events just as regularly as I have, yet have never once made an effort to speak to me or dance with me, even when we’ve been sitting in close proximity to one another. I’m not even getting the chance to show my personality or flirt a little, because it feels like there’s a titanium wall between us. The strangest part is that I’m not doing anything differently with any of these people. I don’t know how else to describe it, other than the overall vibe they give off indicates that they have no interest in me at all.
I once heard that a seven-year age gap in either direction was considered the outer limit for dating compatibility. Ironically, in my experience, the women within that range seem to find me the least appealing. So here I am, having never dated, wondering what on Earth I am doing wrong, or if it will ever happen.
Wanted By The Wrong People
I want to point out something important that I don’t think you’re realizing, WBTWP: there’s a difference between compatibility and attraction. Just as you can be attracted to someone without actually being compatible with them (hoo boy, can you ever…), you can be compatible with someone but not feel anything for them. This is how you can have someone who’s hotter than a volcano god in a heat wave, but who leaves you cold.
Someone can be a great match for you in terms of shared values, backgrounds, interests, ambitions and goals, but that doesn’t mean that you’re going to be attracted to them or vice versa. Compatibility means that the two of you could mesh well as a couple; attraction is what inspires them to want to give it a try.
The fact that a particular person may be a good match isn’t feeling it isn’t a marker of anything other than they’re not feeling it, for any number of reasons. Attraction isn’t a mathematical formula, it’s alchemy and sorcery, and it’s not going to work exactly the same every time because you can’t account for every variable. The stars could be wrong. They could be asexual. You could look like their ex. Or family. Or they just have a weird thing about guys with your specific hair color.
Now, there’re a few things that are in play that make a difference in the reactions you’re getting. One is that the people who are older than you aren’t taking this seriously. There’s a freedom that comes when you’re not concerned or focused on the outcome, one that frees you to just have fun with it. They can flirt just for love of the game, because they’re not worried about what happens next. That doesn’t mean that the flirtation isn’t appreciated; after all, even if you’re not going to the party, it’s always nice to be invited. But the fact that they know, and you know, that it’s not going to go anywhere means that they’re allowed to enjoy it for what it is.
Meanwhile the people who are closer to your age, the ones who you are (theoretically) available and you might want to date? The vibe is going to be different. The likelihood that you’re taking this seriously is significantly higher and that changes the math for them. Especially if they’re used to dudes who are going to dance classes to get laid, rather than to dance. It’s not necessarily personal; many times, that firmly affixed feeling of indifference (the “bitch shield” in PUA parlance) is often about warding off dudes who think that women are objects to be consumed instead of people. So there’s every chance that the issue at hand is just… other people suck. Which, y’know, sucks for you, but that’s how life is sometimes. It isn’t fair, but life ain’t fair, and all you can do is deal with it.
Now there’s also every chance that you’re simply not their type. They may not necessarily want or like the flirty guy, or they think you’re giving fuckboy vibes with the way you’re dancing with the older ladies. Or they may not be single. Or they may simply not be interested in meeting someone at their dance classes – especially if they’re interested in competitive dance or are pursuing it seriously for its own sake.
But the other thing I notice is that… well, it doesn’t seem like you give them much of a chance to actually get to know you. You say that they don’t acknowledge your existence, but it doesn’t sound like you’re even asking them to dance. If anything, it sounds like you’re bouncing off their aura before you ever even talk to them, rather than asking them to dance and getting turned down. So maybe the problem is that you’re treating the way that they’re not as visibly enthusiastic as a wave-off and simply not engaging with them at all. If you were to just ask them to dance and see how the dance goes, you might get different results.
Speaking of different results, you may want to consider whether your flirtatiousness is the issue. One thing that’s incredibly helpful when meeting someone is to adjust your approach to the person, rather than taking a one-size-fits-all attitude. Some people aren’t going to be receptive to the Captain Jack Harkness vibe and will bounce right off of it. However, if you dialed it back a notch or two (or three) and matched their energy, you might get better results.
Think of it like dealing with a big, enthusiastic golden retriever. There’re folks who are going to vibe with that big happy puppy energy and want to roughhouse immediately. Other folks, however, would prefer a lower key level of friendliness from that big dog and not be bowled over with the desire to play. However, once they have a chance to feel comfortable with it, they’ll be ready to toss the ball and give it belly rubs.
And some folks are closer to cats, who would prefer an opportunity to approach cautiously and need to investigate things at their own pace before they feel ready to play.
As a general rule, I’ve found that coming into an interaction at “their level plus 10%” works well. It still can be fun, but without feeling overwhelming, and if they’re enjoying your presence, they’re more likely to raise theirenergy to match yours. This sort of pace-and-lead approach tends to lead to a building sense of fun and connection more reliably than coming in hot; not everyone wants you to be at a 10 when they’re at a 2.
The final thing to consider is that maybe you’re not going to find someone to date at the dance events. That’s also fine; it’s not the only place to meet women, and not everything you do needs to also be in service of trying to get a date. You may have better luck meeting people in different events. That doesn’t mean you’re doing anything wrong, per se, just that things aren’t going to line up the way you need. Especially if, as I said, you’re having to deal with the context of other people’s behavior poisoning the well first.
But I’d recommend focusing on being outcome independent, adjusting your energy to meet theirs and to actually ask them to dance before you assume they just don’t like you.
Good luck.




