Why Enneagram Fives Are Great at Liking People and Terrible at Letting Them Get Close

I used to think that I was just bad at making friends. Not in a dramatic “nobody likes me” kind of way, or because I was hiding behind the excuse that “I’m just shy.”

The truth was stranger than that. I'd meet someone, genuinely like them, sense they liked me too, and then... nothing. We'd stay stuck in that pleasant orbit of good conversations that somehow never solidified into an actual friendship.

When I discovered that I am an Enneagram type Five, I began to realize why. I wasn't avoiding people – I was avoiding what came after them.

The Art of Keeping People at an Arm’s Length

Every would-be friendship starts with a conversation. Most people experience this as a single event, the chat where everything clicks. The Enneagram Five, however, experiences it as the beginning of a potentially ongoing obligation, and we all know how deeply Five’s fear obligations! We’re the type that guards our energy. We worry that being obligated to others will drain our resources and strip us of our much-needed autonomy. Yikes.

For me, this fear showed up in a perverse social strategy where I’d react like a deer in headlights and pull back from the start. Someone chats to me at the gym? I keep it as brief as possible, a polite cold shoulder. A coworker suggests grabbing lunch? I say I’m too busy, even when I’m not. 

To others, it probably looked like someone with social awkwardness or an introvert preferring their own company. But to me, that first, seemingly low-pressure conversation was the first step to a commitment that I did not want, and I was trying to prevent a future version of myself from becoming indebted: 

• If we had lunch today, would they expect lunch next week? 
• If I stopped to chat at the cable machine, would they want me to spot them every time? 
• Would I now have to maintain this level of engagement forever?

The Urge to Push Even Close Friends Away

It wasn’t just strangers I kept at arm’s length. Even with people I'd already been talking to for months, people who by any normal measure should have become friends by then, I found new ways to keep a wide distance. 

My texts, if you were lucky enough to get them, were short and to-the-point. The logic went like this: 

• If I send someone a few long and enthusiastic messages when I am in a chatty mood, will they expect this level of energy from me every time? 
• If I reply straightaway, would I have to do that all the time? 
• What happens when I disappear into one of my rabbit holes for a few days? Would they think I’d ghosted them? Would I have to explain myself?

Even with friends-friends, people who had actually earned that title, I struggled to ask them to go with me somewhere, or even ask for the smallest favor, because, in my head, I was thinking: If I asked for their help today, would I open the door to them asking me for something in return?

Now, I know this sounds selfish, and it isn't how healthy friendships work. Healthy people aren't consciously keeping score or expecting you to maintain the exact same level of engagement or availability forever. They understand that sometimes you're chatty, sometimes you're quiet, sometimes you’re busy and need to disappear into your own world for a while. People have partners, responsibilities and years of relationships they have to manage. Even if I become close with someone, I know I’m not going to be the center of their social universe, and they’re probably not going to ask for more than I can give. 

But no matter how logical that sounds, there’s still a truth that makes those fears feel very convincing to an Enneagram Five – every friendship has some strings attached and sooner or later, you have to pay the piper. 

The Four Wing Soulmate Standard

Buckle up, because this is where it gets complicated. As a lonely person who instinctively kept people at arm's length, I really couldn’t afford to be choosy. Yet I had incredibly high standards for the friendships I did try to make. I blame this on my Four wing.

Enneagram wings are the two personality numbers directly adjacent to your core Enneagram type. You can have a balanced blend of both wings, but most people heavily lean toward one, their dominant wing. For me that’s a Four, and it acts like a sidekick to my Type Five behavior. 

Fours are all about creativity and sensitivity. They strive to be true to themselves and detest anything that feels fake or shallow or ordinary. Sounds great, right? Only when it comes to making friends, the Four part of me didn't just want a friend to hang out with, it wanted someone who understood me on a level no one else could. It didn’t just want a friend who would show up when needed, it wanted a kindred spirit, a platonic twin flame, someone to share secrets with and prioritize each other above everything else. For years, I'd single out one person I clicked with and hope they'd become my “soulmate friend.” I'd had friendships like that as a child and even in college, so I assumed that was what friendship was supposed to feel like. That’s a lot of pressure to put on a fledgling adult friendship!

I cringe now, but I remember getting really mad when a new friend cancelled our plans to meet up with someone else (“Am I not supposed to be the no. 1 priority?”). Another time, I felt seriously slighted because a friend kept certain parts of his life private instead of telling me everything ("Aren't we close enough to share everything?"). 

The paradox is obvious once you can see it. The version of me that recoiled from a lunch invitation was the exact same version of me that expected total exclusivity from the one or two people I did let close. So I wasn't rejecting closeness per se. The more comfortable truth is that I was terrified of any closeness that wasn't happening entirely on my terms, at my depth, on my schedule. Arm's length for almost everyone, and then an impossible standard for the handful of people who made it past that distance. No wonder my friendships never had room to breathe. 

Now it seems obvious that the high-intensity, all-or-nothing energy that comes from needing to know someone on an uncomfortably intimate level veers into toxic codependency rather than healthy adult friendship. But it took me a long time to learn that lesson. And if I’m honest, it was circumstances that nudged me out of my own way, not some grand insight I arrived at through self-reflection. 

My Personal Breaking Point

Tony Robbins once said, “change happens when the fear of staying the same is greater than the pain of change,” and that was totally the case for me. I hit a wall where pushing people away was hurting me more than my fear of being overwhelmed, more than my need for raw emotional intimacy.

When I began working remotely and then moved to a new country where I knew no one, the small circle of friends I’d gathered as a by-product of working at an office and being in one place for a long time disappeared. With that gone, I had a choice – get out there and build a social life from scratch, or continue to live in a complete, unsustainable void. 

The breakthrough, if you can call it that, wasn’t some grand gesture of extraversion or turning up to every event, club and social group inside a 100 mile radius. It was in letting relationships unfold one interaction at a time, without running the numbers on where it might lead before I'd even had a second conversation. 

I just showed up and let people surprise me. 

You Don't Have to Hit Bottom First

I know that advice is a little trite. I could tell you, fellow Fives, that you have to hit the rock bottom of total isolation before you learn to let people in. I could tell you, type Fours and Four wings, that you have to live through the suffocating intensity of one-sided codependency before you understand that's not how most people define friendship, or want it to be.

But I won't, because it doesn't have to work that way.

You don't need a breaking point to see that your fear of engulfment is mostly self-imposed, and that you can test the waters of friendship without diving straight into the deep end. If you're a 5w4 like me, you can start small. You can reply to the text without calculating what it commits you to. You can say yes to the lunch. You can let one friendship stay ordinary for a while before you decide whether it deserves to be extraordinary. Most people are not asking to be your soulmate. They just want to know you a little, and that’s a much easier thing to give.