I’m Doing All The Things Women Say They Want, So Why Am I Still Single?

Estimated reading time: 17 minutes

Dear Dr. NerdLove: I hope you’re doing great. I’ve been reading your column for a while, and since you’re someone who worked at getting better with women, I feel like you can help me with my problem. I’m 25 year old single guy and I’ve gotten tired of being yet another kissless virgin who hasn’t so much as held hands with someone. I’ve been working hard to be more attractive to women. But no matter how much I improve, I can’t seem to make any real connections with them. I’m just super confused and frustrated.

After spending so much time as a dateless loser, I thought I’d put my time to good use and try to build myself into the perfect man that women all seem to ask for. I’ve read tons of articles and watched videos on how to be the kind of guy women would dig, and I’ve been putting what I learned into action.

Over the past couple of years, I’ve been focusing on different aspects of my life to be a better version of myself. I’ve been hitting the gym, eating right, making new friends, and even picking up some cool hobbies.

People always say that women like a confident guy with a good sense of humor, so I’ve been working on that too. I try to be confident without coming off as cocky, and I’m not afraid to crack jokes and have a good time.

One of the big things I’ve been working on is my emotional intelligence. I read what you said about women’s standards and what they’re asking for from guys, and I’ve been trying to put that into practice. I’ve been learning how to be more empathetic, understanding, and supportive. I’ve also been practicing good communication skills so I can really connect with people on a deeper level.

But even with all this effort, I keep getting rejected or worse. Women talk about wanting guys who are open with their feelings, who can be vulnerable and shit and who can be good communicators, right? But then you get someone like me who’s all of those things, but as soon as I get real with someone, they act like I’m nuts or like I dropped my pants and pissed on their foot. I’m not saying that I broke down about my dog dying when I was away at college or anything, but I express the slightest bit of vulnerability or show that I’m an active listener and I hear about how she told her friends that I’m being weird.

And the craziest part is, they seem to go for guys who don’t put in half the effort I do.

This whole situation is just bumming me out. I can’t help but wonder if there’s something wrong with me, or if I’m just not doing enough. It feels like I’m fighting a losing battle, and I don’t know what else to do.

Doc, I could really use some advice. I’m tired of feeling like I’m not good enough, but when I try to be what women say they’re looking for, I get shut down for it. Am I missing something or doing something wrong? How can I finally make some real connections with the ladies?

Doing The Work

You say you’re a long-time reader, DTW, so I hope you’ve seen the times when I said that you should be working on yourself for your own sake, not because you think it’ll make you better with women.

Well… this is why. You end up putting yourself in a position where you feel like you’ve done all this work – and I want to be clear, this was a lot of work, and you should be proud of what you’ve achieved – and it’s not ending up with the results you were expecting.

There’re two big disconnects here that are almost certainly the main reason why you’re having issues.

The first is was your reliance on “what women say they want” as gospel. While there are some aspects that are broadly true – such as women wanting men who are better communicators and more emotionally available – the things that women want is going to vary widely from woman to woman. Yeah, posts Reddit, Insta reels or TikTok may get a lot of views and engagement, but views and engagement aren’t the same thing as a shopping list, nor is every woman looking for all of those things in those exact ways.

One of the mistakes a lot of people make – myself included, back in the day – is that when they try to mold themselves to what they think women want, they usually end up trying to be someone else. They’re functionally trying to go from being Johnny Maidenless to Jason Momoa or Henry Cavill or whatever celebrity terminally-online guys have convinced themselves are the Avatar of Sex this week. The problem is that… well, you’re not them. All you’re doing is trying to put on someone else’s style and persona and attributes and wear them like a bad-fitting suit. Even under the best of circumstances, it’s pretty obvious that this isn’t who you are and you’re about as comfortable in that skin as you are in pants that are a size too small. You might be able to squeeze into them, but it ain’t gonna be a good look and you’re not going to like how it makes you feel.

At worst, however, you’re going to make other people uncomfortable, because it’s the social equivalent of the Uncanny Valley. People can see what you’re going for and what you’re trying to look like, but it’s going to be just… off. You aren’t going to be congruent with yourself and so there’ll be lots of little things that just don’t fit up right, and that’ll put people off.

Now, don’t get me wrong. This doesn’t mean that self-improvement is bullshit or you shouldn’t try. What it means is that you should be working on yourself, not trying to carve yourself into somebody who you’re not. Much like expecting a girlfriend to transform you into a different person, if those aspects weren’t already there, you aren’t going to bolt them on successfully.

This is why “just be yourself” is actually good advice, just applied poorly by others. Self-improvement isn’t about being someone else, it’s about learning how to be your best self, addressing aspects of yourself that need to be changed, polishing other parts and generally leaning into the things that make you uniquely you.

And to be fair: “you” is a concept that’s always in flux. A lot of what we think of as “us” – that core of who we are – isn’t as permanent as we think. More often than not, those are things that we decided are our limits, rather than being the true boundaries of our self or skill. When we say “I can’t wear that, that’s not me”, that may be true… but that’s only because that’s something you decided, not something that is carved in stone. So it’s absolutely possible to, say, pick up a hobby or interest that you would’ve sworn was “Not You” or dress in a way you never would’ve thought you could pull off.

But that’s different from trying to be someone that other people think you should be. Picking up “cool” new hobbies isn’t useful if those hobbies aren’t things that actually speak to your soul or your interests. I can go to a hockey game and have a good time and be surprised by my enjoyment of it, sure. But if I tried to get into hockey just because I thought I needed to be into it to be popular with women, then it wouldn’t work. You can shove martial arts, “getting fit”, or any of the other usual recommendations into that same pile. If you genuinely enjoy working out or lifting weights, then that’s awesome! If you find that you like the benefits of that workout or studying martial arts or taking dance lessons, then I’m happy for you. But if you’re taking those up because someone else told you that this is what you need to be attractive to others, then all that’s happened is that you’re trying to be someone else’s idea of sexy, not embracing what makes you sexy, specifically.

The second disconnect you’re having is the idea that you make these changes and then boom, you reap the rewards. Let’s use emotional intelligence as an example, since you bring it up in your letter.

You talk about how you’ve been working on being more in touch with your emotions, more vulnerable, more empathetic, better at opening up and so on, only to have people respond badly instead of positively. Just communicating that you have emotions isn’t emotional intelligence. Part of that intelligence is the when and how you share those. But I’m going to be generous here and assume that you’re both being genuine in those moments and you understand the difference between being vulnerable and unleashing a torrent feelings like you’ve got the emotional equivalent of norovirus.

There’s a hard truth to be had here. Part of why it can be hard for men to cultivate more emotional IQ, even when people are literally begging us to do so, is because, frankly, a lot of people aren’t used to it. Seeing a guy who’s actually kind of got his shit together, is ok with being vulnerable – when it’s appropriate – and is able to make space for, understand and reflect other people’s emotional reactions? That’s going to seem weird or unusual to some, especially when they’re more used to guys who are more closed off. You can want something, but still not know what to do with it when you have it.

Part of having emotional intelligence is understanding that.

And that’s before we even get to women who have reason to be cautious around dudes who wave around their “sensitive, thinking man” cred like a banner. There a lot of folks who make a big performance about their emotional intelligence or feminist cred or whatever who were actually predators in disguise. A quick Google search on Hugo Schwyzer can be helpful as to why some folks get their guard up around dudes who make a display of how Not Like The Others they are.

(We will now pause to appreciate the irony of my saying that…)

Another aspect of it is understanding that just displaying these new traits like the tail of a peacock that finished therapy isn’t the point of cultivating emotional IQ. You don’t do it because you can wave your certificate of “look, I understand my own feelings” and get laid as a rewards. You do the work because it makes your life a little better and makes things a little better for the people in your life, too. It makes you a better potential partner; it doesn’t guarantee you a partner.

My suggestion is that you may need to take a little time and do some self-reflection. Get real with yourself – actually real, not just kicking yourself in the nuts and calling that being real – and ask how much of this is genuinely who you are and how much of this is you trying to be someone else. If you’re not in touch with your authentic self, then how can anyone else be?

Some changes you’ve made may need to go by the wayside. You may need to go back to basics and approach aspects of your new life from a different angle – one that’s genuine and congruent to who you are, not just trying to fill a shopping list. People who are going to want you are going to want you because you’re the best version of you, not someone else’s vision of What Women Want.

And to be clear: that doesn’t mean that you’ve wasted all this time. You’ve made a lot of progress, and you should be proud. It’s just that sometimes the path of self-exploration means you go down some wrong turns or dead ends and need to backtrack a bit. But if you can see this as your learning more about yourself and becoming more in tune with your true self and highest good? Then that’s not a waste of time; that’s you learning more about who you actually are, rather than who you think you’re “supposed” to be.

Good luck.

Hi Doc,

Just recently started to read your column, and it’s super informative. I wanted to see if you can give me some advice because it feels like my head is about to explode.

My girlfriend and I have been in a relationship for 5.5 years now and we are in love. We’ve discussed a future together and are planning on staying together for the foreseeable future. However, there is an issue that I have a problem with and it is our sex life. My girlfriend in the past has always portrayed herself as being someone who is “down for whatever”, but there are moments where it isn’t happening at all. We’ve had many discussions in reference to our sex life and how I feel like there should be more physical since we only see each other 3 days out of the week.

It sucks because, admittedly, I am not someone who can contain one’s emotions and I can become very distant when I am denied sex. We’ve discussed in the past about my performance, and I have done many things in order to better our sex life, but still I feel like once out of the week is too little for me. 

I feel awful for being this way because then I start to feel extremely guilty for the way I act. Especially since I know in my heart that this woman is very special and I’d be a fool to leave her, but this feeling of sexual angst is leading me to look for other avenues to release that stress.

Please help me realize if I am in the wrong? Or if there is any other solution to get around this?

Please Help!!

Frozen Out

So, I feel obligated to start this by pointing out that once a week isn’t that bad for a couple that’s been together for nearly six years, especially if you’re only seeing each other three times a week. But hey, I get it; you’ve got your sex drive and you want more intimacy with your partner. That’s absolutely legit.

I do, however, wonder if frequency is the problem, or if there’re other aspects to this that need to be addressed. Sometimes focusing on how many times you’re having sex – by which I’m presuming you mean penetration – ends up obscuring possible solutions or compromises.

I kind of wish you’d given me more information, FO, because I have a lot of follow-up questions. The first, admittedly is “what does ‘down for anything’ mean?” This is a really ambiguous statement that could mean that she’s willing to try different things, even if she’s not necessarily into them, it could mean that she’s willing to have sex whenever… and if you and she have different understandings of what that means, that could be the core issue right there.

I would also like to know what, precisely, you feel like you’re missing by only having sex once a week. I don’t mean this as a judgment of you, but as a way of getting to the actual things you feel are lacking. Is it just that you want more orgasms, straight up? Is sex part of how you feel connected and valued by your girlfriend? Are you missing the overall sense of intimacy that comes with sex?

Understanding what, precisely, you feel is lacking is important to addressing that lack. Sometimes the issue is that what you’re asking for and what you want are two different things.

But the most pressing question I have is: ok, you’ve talked about your sex life with your girlfriend and your performance, but have you asked her about her end of things? How does she feel about the sex you all are having? Is she frustrated by the frequency too, does she just have a lower libido than you, are there other things that might be affecting her desire in general?

See, that last one’s important, because that could be an important clue that could tell us whether the issue is just mismatched libidos or something else.

Case in point: one of the things that leaps out at me in your letter is your awareness that, if you feel “denied” sex, you get distant. That’s a little troubling on multiple levels, FO. The phrasing alone is going to send some people’s hackles up. If you’re framing your frustration as being “denied” sex by your partner, especially to her, then you’re going to run into problems. Saying you’re being denied makes it sound like you’re being refused something that’s yours by right. Even if you don’t mean it that way, that framing and phrasing can hit differently on an emotional level and exacerbate an already-existing issue. If your girlfriend’s feeling unsexy, tired or otherwise isn’t interested in sex right now, saying that she’s “denying” it to you is going to make her even less interested.

But the fact that you “get distant” when you feel like you’re being “denied” sex is almost worse in some ways. Whether this is what you intend or not, that can end up feeling like you’re trying to punish her for not putting out. Getting the silent treatment for not having sex is the sort of thing that builds resentment in a relationship. If she’s having other issues, like a lower libido or feeling unappreciated or just not enjoying the sex you’re having, then getting the freeze-out is going to just be the cherry on that particular garbage sundae. Again, while that may not be what you intend, that can leave her feeling like you see her as a sex-dispensing machine and not just your girlfriend. That’s a pretty dehumanizing way to feel, you know?

This is why I think you and she need to have an Awkward Conversation. I know you’ve been talking about issues with you sex life already, but I wonder if you’ve been as fully honest and vulnerable about it as you may need to be.

So schedule out a time to talk, when you both know you won’t be interrupted. Ask her to hold any questions or interjections until you’ve said your peace. Lay out precisely what you feel is missing and why this bothers you. Don’t just say “I want more sex”, especially if that’s not the ultimate issue. Explain what you’re feeling, what you’re missing and why that bothers you. If it’s because you feel less loved or less connected with her, tell her.

And if it is a case of wanting more sex, period… well, say that too. Explain how you feel, why you feel this matters and – importantly – what some possible solutions might be and why that would make things better.

BUT. Once you’ve said YOUR side of things, you then say “and how about you?” Then you let her share her side. How she feels, what she’s been experiencing, how she sees this. And – importantly – you accord her the same respect that she gave you. Yes, you may feel like you need to jump in to explain or clear the record. Stifle that impulse. She was quiet until you finished, you can be quiet until she does.

Once you and she have both explained your side of the situation, make sure you understand what she’s saying. Say, out loud: “Ok, I want to make sure I’m understanding you. You’re saying…” and then repeat her argument as you understand it, in your words, to make sure you’ve got it. This will also be the invitation for her to do the same for you and her understanding of your side of things.

Once you both have a grasp on what the other is feeling or how you and she see the situation, then you seek compromise. If there’re things affecting her desire for sex, then that may mean that you need to give her a hand there, even if it means just being understanding and adjusting your expectations. It could well be that backing off and – importantly – not giving her the silent treatment will free up the emotional bandwidth that she needs to handle things on her end.

Or maybe it will mean that you change your definition of what “sex” is, to be broader than just tab-a-into-slot-b. If sex meant that you were getting penetrated three times a week or more, you might get tired of it too. But if you and she can reach a compromise where there’s still intimate contact but not penetration, you’ll be getting more orgasms than you currently are (and vice versa). Oral sex, a masturbatory assist, even some dirty talk while you jerk off can all be ways of fostering that intimacy and connection and physical pleasure in ways that could work for both of you.

Or if it’s an issue of feeling connected and valued… well, maybe there’re other ways you can achieve that without trying to force desire where there isn’t any. Massages, especially foot or back rubs without expectation of it turning to sex, for example, can be an incredibly intimate and sensual experience. So could, say, a long, relaxing bath together.

But also, keep in mind: those compromises work both ways. You may need to be willing to give yourself the ol’ five-finger shuffle or invest in an insertion toy like a Tenga for those times when you need to get off but your girlfriend isn’t willing or able. Yeah, it’s not exactly what you want, but I can promise you it’ll help tide you over until she is feeling it.

Incidentally, if you’re aware you’re giving her the freeze-out when you want sex but aren’t getting it and you’re still doing it, even knowing that it’s not helpful and likely hurts her? Then you may want to seriously consider talking to a counselor about why you do this and how to stop. Knowing that you’re doing a bad thing doesn’t get you points when you continue doing it. If you’re legitimately having difficulty NOT doing it, then digging into how this became a conditioned reflex for you is going to be important.

And if that’s not enough of a reason to go talk to someone, consider this: that may be the step that saves your relationship from your own unhelpful behavior.

Good luck.