I’m Struggling To Connect With Women. What Am I Doing Wrong?

Estimated reading time: 12 minutes

Hi Doc,

I’m reaching out because I’ve been feeling a bit lost when it comes to relationships, and I’m hoping to get your perspective. At a recent event, I found myself feeling unexpectedly envious and isolated, which made me realize that there are some things I need to explore and understand.

A bit of context: in my twenties, I didn’t always make the best choices when it came to friendships. I’m naturally empathetic, and I’ve always felt a strong connection to people going through hard times, given that I’ve experienced my own challenges. Unfortunately, most of those connections ended up being unhealthy for me, and I had to let go of them for the sake of my mental health. Most of my social circle back then was made up of women around my age, many of whom I met in university. I’ve always connected more easily with women than with men, and this was a big part of my social life.

Since the lockdown, I’ve been trying to rebuild my social life, but I’m essentially starting from scratch. It’s been a bit of a mixed experience. I’ve met a lot of people and I’m generally well-liked in the circles I’m part of, but I haven’t found any deep, lasting connections. I’m starting to think it’s a compatibility issue. Most of the people I meet are either older, already have their established groups of friends, or are in relationships, so their time is limited or they don’t seem interested in creating new, sustained bonds.

Despite this, I keep getting unsolicited praise, telling me how great I am. Whether it’s in professional settings or through my hobby groups, I get constant compliments — how I’m “amazing,” how I “should” be in a relationship, or how I’m “attractive.” It’s all flattering and I do appreciate it, but it also creates this odd distance. For instance, a group of women I see in one of my hobby classes recently got together for drinks and apparently had a conversation about how surprised they were that I’m still single. I never know how to respond to comments like that, especially since I’ve never been on a date, so I usually just deflect and move the conversation along.

Here’s the thing: despite all the positive feedback, I’ve noticed that women in my age group (roughly 20-30) don’t seem to be interested in connecting with me, even at surface level. Aside from a couple of women I met in one particular class, the majority seem either distant or uncomfortable when I try to engage with them. This is even when I do get a chance to interact, which doesn’t happen often. They’re not always women I find attractive either, so it’s not as if I’m putting them on a pedestal. It’s really frustrating, and I’m not sure how to navigate it – especially since all the external signs suggest otherwise. This is where the feelings of envy and loneliness start to creep in. I want to connect with these women and possibly date, but it feels like they’re just not interested. As a result, I’m starting to feel like I’m somehow not worthy of their attention or a meaningful connection.

It’s especially confusing because, as I said earlier, throughout my life I’ve always been able to form easy connections with women – people who found me fun, comfortable, and easy to talk to. That seems to be missing now, and I’m struggling to figure out why.

I’d really appreciate your thoughts on this, as I’m not sure where to go from here.

Connection Error 633

This isn’t something you asked about, CE6, but this leapt out at me and I think it’s relevant: “I’ve always felt a strong connection to people going through hard times, given that I’ve experienced my own challenges. Unfortunately, most of those connections ended up being unhealthy for me” and “Most of my social circle back then was made up of women around my age”.

This is something I’ve seen a lot in guys in situations like yours. Hell, it’s something I see in who I was back in the day: it’s White Knight Syndrome. It’s the sense that you aren’t “worthy” enough to “deserve” love or affection or companionship on your own, and so you have to “earn” it in such a way that it elevates you. It’s a form of neediness and it’s not surprising that it ends up leading you into relationships that were ultimately not healthy for you. Toxic people love White Knights; their boundaries are weak and they’re easily manipulated because they don’t feel like they have the right to things like standards or boundaries.

But even when you’re not dealing with toxic asshats who’re taking advantage of you, you’re still putting yourself in positions of trying to help with problems that you simply can’t help with. You lack the qualification and training, and enthusiasm and a can-do attitude aren’t going to make up for it. And that’s before things like “caretaker fatigue” set in and the frustration of realizing that YOU aren’t magic enough to fix a problem by existing.

The thing is White Knight Syndrome – like a lot of forms of neediness – only gets resolved by developing your own sense of worth and internal validation. Without that, folks tend to go down one of two paths: leaning even harder into it (leading to outcomes that are commensurate with said leaning) or falling into a malaise of confusion and despair.

That second outcome tends to also come with a side of greater passivity and giving up your sense of control – something that I think is what’s plaguing you now.

Here’s the thing: the reason you are confused by things like your fellow hobbyists being surprised that you’re single is two-fold. The first is that you’re on the other end of something I point out to folks all the time: we don’t see the entirety of a person’s existence. We only see a small sliver of it, and only the parts that we’re there for – never the context, never what leads up to it or comes after. Your hobby friends are seeing how you behave when you’re around them and extrapolating based on that.

Because you’re acting in a way that reads more relaxed, personable and comfortable, they’re assuming that you’re like that all the time. It follows that they would then further assume that this would make you considerably more in demand as a partner.

But they’re not seeing the way you behave and act when you’re not there, nor do they have the 24/7 feed of the inside of your head. So they’re basing their assumptions about you on the highlight reel, not the unedited footage. In this case, it’s more positive than comparing your unedited footage to someone else’s incredibly curated portfolio piece, but that’s part of the disconnect.

And it’s what they’re not seeing – and honestly, what you seem to not be seeing – that’s part of what’s cooking your noodle here.

Looking at your current situation, what I’m seeing is someone who gives up at the first sign of friction, whether real or imagined. The big reason you’re struggling to make meaningful connections is that you’re being very passive and only willing to make an effort if the path is as smooth and as clear and easy as possible. Anything else and you give up quickly.

There’s a lot of points in your letter where you’re making assumptions about people based on your view of yourself and letting those assumptions dictate your actions and poison the outcome. Take, for example, the idea that folks with social circles are simply done making friends. While it’s often true that trying to find time to hang out with your friends gets harder as you get older, that’s very different from the assumption that they’re just not interested making friends or meeting new people, or integrating new people into their social circle. That’s drawing a lot of conclusions based on facts not in evidence and it goes right back to that low sense of self-worth. You’re telling yourself that people who already have friends wouldn’t be interested in also being friends with you or bringing you into their social circles because what reason would they have to bring you in? You feel as though the people who would want to be friends or have a closer, more meaningful relationship are folks who don’t have better options already.

The problem here is that because you think these folks couldn’t possibly be interested in you because you’re you, you don’t put in the same level of effort that you would otherwise. You’ve assumed you’ve failed before you even started, and so you half-ass it… maybe even just quarter-ass it. But the fact that you’re half or quarter-assing it is a big part of why you fail; making friends requires you give them the full ass.

The same goes for people who are older or who are in relationships. Yeah, they may not be the people you want to date… but they can be your friends. You can have friends who aren’t within +- 2 years of your age you know or who are partnered. And they also know other people – people who may well be single and looking for a guy like you!

But to do that, you have to be willing to put more than a token effort into trying to make friends with them. You also have to stop deflecting or pushing people away if they bring up your good qualities or say things like “wow, I’m surprised you’re single”. It’s a lot harder to build the sorts of connections you want when you keep swatting compliments away or refusing to accept that maybe people honestly think this about you.

When they bring up their being surprised that you’re single and you deflect or change the topic, you’re reinforcing your own feelings about yourself. You’re trying to ward off the possibility that you may be more than you believe because… well, because you won’t let yourself believe it. You could say “yeah, it’s a mystery to me too, so if you know anyone you think I might vibe with, hook a dude up!” or even “aw, thank you! I sincerely appreciate that!” Instead, you refuse to accept it and – in the process – put another barrier between you and people who are trying to be your friends.

This is why solving you issue requires that you stop assuming that you are so unworthy, so unlikeable that people “with options” wouldn’t like or accept you. You have to be willing to invest time and energy into making friends and realize that the key to building and maintaining stronger friendships is regular and repeat contact instead of trying to speedrun it and deciding that it’s impossible when it doesn’t work out.

And honestly, there’s a lot here that makes me wonder how much of that the unwillingness or discomfort with being closer you mention is your perception rather than reality. I suspect that at least part of the issue is the way that you’re going about trying to get closer with people.

I wish you’d said more about your efforts and what actually happened, because the vague generalities you give are, well, vague and general. They don’t provide much insight or data to work with.

There are, however, a few things in your letter that make me think that your behavior changes when you’re trying to get closer with people.

Let me ask you a serious question, and I want you to put some thought into the answer: do you tend to get more intense or more personal with those people you said seemed distant or uncomfortable? Is it possible that, because you feel like you’re trying to achieve a specific goal here, that you get a little over your skis? I ask because hooo damn did I get the same way, back in the bad old days. I have snatched defeat from the jaws of victory far more often than I care to think, because I got weird about it, instead of just being the guy I was when I wasn’t trying.

Yeah, I know, “try without trying” is like a stupid person’s idea of a Zen koan, but it’s true. Think of it like Bill Murray trying to win over Andi MacDowell in Groundhog’s Day. You can watch him try harder and harder to make it happen, especially after he almost got there the first time, and it keeps getting increasingly less authentic, more desperate and more disturbing.

I suspect that’s part of what’s going on and what’s getting in the way. It’s not about the effort, so much as the intensity. And that intensity is there because you’re struggling with that sense of worth and deservedness; you end up feeling like you’re in a race to lock things down before they wise up and reject you. And because you’re coming into these interactions half-rejected in your own mind, you end up starting off feeling like there’s not much point and so you barely try. However, when there’re times when you sense that there’s a chance you might pull it off this time, you get keyed up. Either way, you end up making a mess out of it and just reinforcing the idea that you’re not worthy.

You are capable of impressing people and getting them to like you and be interested in you when you aren’t actively trying to get them to date you. Those hobbyist friends who are surprised you’re still single are proof. The way you behave with them is the way you should be behaving with the people you might want to be closer with or might want to date – just with more intentionality, less passivity, and a hell of a lot less giving up so quickly.

A lot is going to be contingent on slowing your roll and letting things develop at their own pace. Taking the energy you have with the hobby friends you’ve impressed and bringing that to having some one-on-one conversations with the folks you want to get closer to, without angling for more, will get you a lot farther. Most friendships tend to be born out of just hanging out and talking; the closeness and intimacy comes as you get to know each other and earn one another’s trust. That takes time.

But that is going to require that you let go of a lot of assumptions and prejudgments. You’re going to have to focus on enjoying the conversation for the conversation’s sake, rather than seeing it as the first step onto a relationship escalator. And you’re going to have to start learning how to see your own worth and embrace your own value ­– seeing yourself as someone folks would love to get to know, not the lesser option. This is why I keep telling people: you have to be your own best friend and biggest hype man. Gas yourself up the way you’d talk up your best friend. Treat yourself like a priority, not an option, so you stop thinking that’s all that you deserve.

That makes it easier to actually want to invest the time to make friends and to push past the first signs of friction. If the only way you can connect with people is if the path is as smooth, straight and direct as a drag race, you’re going to be holding yourself back from a circle of friends for a long, long time.

Start building yourself up, and then pair the same sort of behavior that’s charmed your hobby circle crew with purpose and intention. I think you’ll find the connections come a lot easier and more often if you stop thinking that you’re the lesser choice in the buffet.

Good luck.