How Do I Make REAL Friends, Not Superficial Connections?

Estimated reading time: 12 minutes

Dear Dr. NerdLove:

I regularly do social activities and hobbies, but I’m just completely unable to make any close friendships or any connection beyond the superficial. I have a mental block that prevents me from starting conversations with anyone, including people I know. Any time someone does start a conversation with me, I’m caught off guard, and I don’t contribute to the conversation in any meaningful way. I pretty much just go “uh-huh”, “cool”, or “yeah”, until the conversation fizzles out, and I only realize after it’s over what I should’ve said. No matter how much I try to imagine a conversation and how I could make one better, when a conversation actually happens, I’m caught like a deer in headlights. Alternatively, I think of something I might want to talk about, but I don’t know how to bring it up, or I don’t know if it’s too personal or would make them uncomfortable.

When it comes to starting a conversation, it’s an even bigger mental block. I never know when it will be acceptable to do so. Everywhere I go, I see people already talking to others. And even when I see someone alone, not talking to anyone, it still takes so long for it to even come to my mind that I should talk to them that either they go and do something else, or it would probably be awkward to suddenly start talking after lingering.

I don’t know if I should ever message anyone or even what would be appropriate to message them. I don’t know if messaging them would annoy them.

Whenever I’m in a group conversation, I don’t often contribute in any meaningful way. In my mind, I keep thinking about how I could contribute, and wait for an opportunity to do so that I can’t fully pay attention to the conversation, or I get distracted by something else. I think that any group conversation I’m in would be exactly the same even if I wasn’t there.

And I have no one to blame for any of this except myself.

How do I get better at social skills and make real connections beyond the superficial?

Chronic Wallflower

This is interesting, CW, because I can relate to some of this and some of it seems alien to me. For example, I know I have plenty of times where I would love to reach out to some people via text, instant message or social media, but I worry that I’d be bothering them or that they wouldn’t want to hear from me. Which is made all the more ironic when I see friends –  people who I like and respect very much talk about how they worry that they’re bothering people when they DM them. Meanwhile I’m sitting there saying “I am pretty much ALWAYS interested in talking to you”.

So never let it be said that this shit is logical.

The fact that you can’t think of anything until afterwards is something everyone experiences. It’s what the French call “l’esprit de l’escalier” or “the spirit of the staircase” – that moment when you’re walking away when you realize the EXACT PERFECT thing to say. So you’re hardly alone in that. 

Now, in your case, this doesn’t sound like a lack of skill or will so much as an anxiety response. I have a lot of questions that I’d love an answer to, like whether this is a relatively recent experience for you or if you’ve had issues with this all your life. And if it is a relatively recent change, what may have preceded it. If there was a particular inciting incident, then that might give more of an idea of why you have this particular block and how you could work to get around it.

I’m also curious as to precisely how this block feels, to you. Is it that always you can’t think of anything good or appropriate to say? Is it that you have SO many thoughts going at once that you can’t settle on just one? Or is it that your brain just vaporlocks when someone starts talking – you’d love to respond but your brain is just a dialtone now.

Some of what you describe – not knowing when it’s appropriate to jump into an ongoing conversation or how to start a conversation with someone else – sounds like a classic case of social anxiety and social awkwardness. A lot of times, this comes down to a feeling that you are being judged and measured and have to be “perfect” in order to make it through every social interaction.

You’re not alone in this. A lot of people worry that if they’re not the soul of Wilde-ian wit, dropping bon mots the way that a clumsy waiter drops forks or navigating the often chaotic nature of a group conversation with the skill of a pilot doing the Death Star trench run, they’re going to be exiled from society. But the truth is… these are all really just mental distortions. We vastly overestimate how likely people are to notice any malaprops, verbal missteps or just plain mistakes and overestimate how much they’re going to care. Similarly, we underestimate how much someone – such as that person standing by themselves, not talking to anyone – would appreciate somebody coming along and saying “hello”, even if it’s not as smooth as a fresh jar of peanut butter. 

Part of the problem is that we’re all the center of our own universe. Because we have a constant, 24/7 stream of our own perceptions, our own thoughts and our own feelings, we feel like other people are aware of them too. But the truth is that most folks are too caught up in their own shit to spare the bandwidth to give more than a single “…huh” to any mistakes we might make.

One of the ways you can get past this – especially while you work on other aspects of what you’re worried about – is to put the focus on other people. By giving someone else the spotlight, you feel less pressured to perform under the (not actually) withering gaze of others. The easiest way to do this is to just ask questions and let the other person talk. As I’m often saying, most people rarely talk to somebody who genuinely wants to listen; everyone is usually just waiting for their turn to talk, instead. By being willing to be the person who wants to hear their life story or their opinions on tropical fruit or whatever, you are giving them a gift. And of course, the best part of this is that it means you rarely have to worry about not having something to say. As long as you’re an active listener, other people will give you plenty to react to and to use as springboards to more questions.

Now there are risks to this. To start with, you’re not James Lipton and this isn’t “Inside the Actor’s Studio”. 

Unless you are, at which point I’d want to know how you came up with the Thundercats theme. And also how you wrote me this letter – dictated via Ouija board?

But my point is that what you want is conversation, not an interview. Think of a conversation like a tennis match. The initial question – “hey, what’s your story?” – is the opening serve. When they respond, they’re functionally volleying the question over the net back to you. You, then, take that answer, respond to it and put your own spin on it or relate to it, then ask your next question based on what they said. This lets you keep things going until either you or they drop the ball… at which point you serve the next question or topic.

The other risk is that many people will realize that they’re dominating the conversation and turn it back around to you… and now you’re right back to the very thing you hope to avoid. Which is what actually leads to my next point, conveniently enough.

The other part of the problem you’re experiencing, is that you’re stuck in your own head. You’re so busy thinking about what to say or how to say it that you’re not actually able to participate in the conversation at all. So it’s not really a surprise that your responses are experiencing some lag and you only come up with a better thing to say after the fact. You are, for all intents in purposes, off in your own little world and the signal takes time to get there. 

And you’re also rapidly running out of oxygen.

So how do you get past this? You stop thinking so much. Yeah, I know, you’re thinking about everything because you’re worried about making some sort of critical misstep. Well allow me to point out that you’re able to navigate in the world without having made mortal enemies of your employers or authority figures in your life, nor have you been run out of town for saying something so egregious that nobody could tolerate having you in their presence for a moment longer. You have made it this far in life without having been so offensive that nobody would allow you to be part of polite society. So perhaps you might be willing to cut yourself a bit of slack and not worry quite as much about being “perfect”.

Of course, it’s easy to say this. It’s a lot harder to put it into practice. But practice is precisely what you need – practice in reacting instead of thinking, in just being in the moment instead of being in your head. It can seem a little counterintuitive, but thought often is the enemy of wit. If the secret of comedy is timing, then the last thing you want is to be in a ten second delay. So, by getting better at being in the moment and just responding, without being as worried about it being the exact right thing to say is going to be invaluable. 

But how do you get to that point when you’re regularly drowning in flopsweat over basic conversations? Well, you take classes. 

Specifically, improvisation classes. 

Here’s the thing about improv: we tend to think of it as being all about people having the funniest, cleverist ideas and being able to toss all these hilarious jokes, gags or bits out at a moment’s notice with just a prompt from the audience. But that’s not how it works at all. It’s not about being funny or clever; in fact, trying to be funny is the opposite of what you want. Improv is about being in the moment, reacting to what others have given you and building on it. If you’re thinking about what to say next or trying to get this perfect funny line out, then you’re doing it wrong. You’re not being in the moment, you’re being in your own head. You’re not building with others, you’re trying to show off – the opposite of collaboration. And conversation, when done properly, is a collaborative exercise. If you’re focused on the right thing to say or trying to get to a place where you can say the thing you’ve got in mind, you’re not collaborating any longer.

In improv – especially at the most basic level – you’re trying to work with your scene partner and work with what they give you and vice versa. That means that you work at paying attention to the important things – the settings, the setup, your character, their character, etc. – and let those be what inform what you say next, in that moment, without planning it in advance. Thinking slows you down, creates delays and means you’re not paying attention. That, in turn, breaks the scene. So you learn to stop thinking and just start doing instead. Being funny in those cases comes from the setup and buying into it as wholeheartedly as possible, rather than having the gift of gab and a filing cabinet of humorous responses. 

So it is with having interesting and productive conversations with people. If you stop thinking quite as hard about how to bring something up or how to find the perfect response and instead focus on responding to what they say, right then and there, you’ll find that things flow much more smoothly and organically. 

Now, improv is a skill – a Voltron-like gestalt skill built out of other, related skills, but a skill none the less. That means that you’re going to go through the same progression as you would with any skill – unconscious incompetence, where you’ve never done it before, ever and so don’t know what you’re doing; conscious incompetence, where you are all too aware of what you don’t know and what to do; conscience competence, where you can do it, but it takes effort; and finally unconscious competence, where it becomes something you do without thinking. So you have to be willing to embrace the sucky part, where you feel awkward and ungainly and are absolutely sure that you’re fucking up to levels that nobody in history has ever fucked up before. But by pushing through and not letting that throw you, by continuing to practice that skill through deliberate use, you’ll get to the unconscious competence stage much faster than you’d realize.

Once you get to the point where you realize that you don’t need to think as much about maintaining conversations, the rest  becomes much easier. You won’t be as worried about trying to find places where you could join into a group conversation, because you’ll just see an opening and go for it… like pretty much everybody does. Nor will every conversation just be moments of someone trying to connect with you only to get monosyllabic answers in return. 

Getting out of your own head will make it that much easier to actually make connections with people, where you’ll realize that getting personal or sharing things that connect to your core values and interests isn’t so bad or scary. In fact, you’ll quickly realize that most people enjoy those deeper, more meaningful conversations, because they give us genuine insight into the person we’re talking to.

Of course, now I’m going to throw a curve ball at you. One thing that helps, especially when you’re trying to break through a block like the one you’re dealing with, is going to be the opposite of everything I just told you. I would recommend having three or four stories or anecdotes – but no more than that – locked and loaded in your back pocket at all times, stories that you can fire off without needing to think. These are useful for when you have those dial tone moments and you can’t think of anything else, or you’re powering through an awkward silence. You don’t even need a smooth segue; sometimes, all you need is a “hey, that reminds me, check this out…” to transition into it. The benefit of these is that you can have them ready for specific occasions, and have worked out the narrative rhythm, proper inflection and pauses for responses in advance. 

Over time, you won’t need them as often as you might at first. But just knowing that you have something locked and ready to go in case of a conversational emergency will give you enough confidence to go and get one started. 

Oh, and one more thing. You – and everyone, really – are vastly underestimating how much your friends would appreciate getting a DM or instant message from you. You don’t need an excuse or “good” reason outside of “I like talking to you”. So reaching out with a “Hey, we haven’t talked in a bit, how are you?” or “I saw $CRAZY_THING/$FUNNY_THING/$GOOD_THING and thought of you, what’ve you been up to?” 

I think you’ll be surprised (and gratified) by the response. 

Good luck.