A Scotsman, a Mexican and an Australian go to a bar…

It could be the start of a joke, yet this was actually a regular occurrence when I lived in Bogotá, Colombia in 2014. I met Alan (Mexican) and Pete (Australian) when we lived in the same group house.

We quickly became close friends and spent the next several months with constant hilarity, nightly family dinners, weekend trips, and lots of partying. It was a glorious time in our early 20s that could never be replicated. 

Fast forward to 2022. The three of us met in Tepotzlán, Mexico. I was going through a divorce and in a very challenging place emotionally.

I was in no mood to party, and I was unsure and a little anxious about how we would navigate this time together. After all, our friendship was borne from partying and hedonism.

I needn’t have worried. Without any prior coordination, it transpired that each of us had brought some sort of ritualistic artefact to promote calm and healing. Instead of beer, cigarettes and Aguardiente (Colombia's national liquor), we had candles, palo santo, and incense.

Cue much hilarity about where we had come from to arrive together at that moment.

Noticing a misalignment

I was blown away at how each of us had evolved in our unique ways and yet had come together on a similar vibe after all that time. I felt extremely grateful and we supported each other immensely in those days.

We could connect in ways that were healthier and more reflective of who we are now, while keeping the history and nostalgia and the memories that originally brought us together.

This combination is wonderful, but it is not guaranteed.

As we do our inner work, not all friendships will evolve in this way. Perhaps the types of conversations that nourish you have changed - you want to “go deep” and your high school friend isn’t comfortable with your vulnerability.

Instead of going to a bar with your college friends, you’d rather go for a hike, do crafts or chat over tea.

When you start to notice this friction, it can feel highly unsettling. Childhood and young adult friendships are very special - you know each other’s families, you were witness to each other's formative experiences and many “firsts”.

There is a shared history that cannot be replicated by new friendships. Naturally, there is a part of us that does not want this to change or “lose” those long-term friendships.

Experiencing yourself and the world differently

When we met our friends at high school, college or a previous job, we were at the same stage of life and we saw the world similarly. We shared something important in space and time.

As you embark on your journey of self-discovery, you experience yourself and the world differently. The essence of what you are looking for in a friendship is shifting. What interests and nourishes you is changing.

That’s not to say that the way you approach life is better or worse than the previous version - it’s simply a different way of being. And that translates to different types of conversation, different levels of depth.

Spending time with old friends can feel more effortful now than it once did. Outwardly you may still appear the exact same to your friends. Your friends expect you to be the same, to do what you’ve always done together, to have the same conversations.

You don’t feel secure enough yet in the person you are becoming, so you slip back into a previous version of yourself, and it feels like wearing a shoe that doesn’t quite fit anymore. Such regressions are totally normal.

You spend the night reminiscing about old times. This is amazing for a while, but can be draining when the friendship itself is nostalgia, frozen in time.

Often, it’s not the friendship that feels wrong - it’s the version of ourselves we revert to inside it.

It's very important to notice if we judge others and compare at this stage - a form of self-protection that can arise when we become more conscious yet feel self-conscious about it. When I experienced this, it helped to catch myself when I was on my "spiritual high horse".

I went to one of my closest friend's bachelor party with a group of guys from high school who I hadn't seen in several years. Having developed meditation and yoga practices, started therapy, and read several psychology and self-help books, I felt I was unshakeable and secure in my new identity.

Turns out I was not as secure as I thought. I presented as the 30-something year-old man I was at the time, but inside I was being driven by a nerdy, shy, socially-awkward teenager*. This is the version of me I subconsciously told myself they knew and expected. The regression was humbling.

While we still had fun reminiscing and creating new memories, I knew I was performing and afraid to show them who I was becoming.

*I am still a little nerdy, shy, and can be socially-awkward, but I now embrace those qualities rather than let them control me.

We can break up with a romantic partner. What about a friend?

Here's the thing. This is rarely a black and white scenario where we have to decide to break up or not. That’s the beauty of friendships. They can expand and contract, and closeness can change over time.

Some friendships and acquaintanceships naturally fizzle out and we do not need to be proactive. For others, there is too much history and prior closeness for this, and a clear break or an honest conversation may be what we need.

Maybe you feel close enough to your old friend to share what you’ve been discovering about yourself. Or to share something about your friendship that has been troubling you but haven’t felt able to mention before.

It could be this level of honesty and authenticity that allows the friendship to grow and deepen. Your friend may respond that they are on a similar journey but have also felt unable to “come out”, to be a black sheep in the group where the status quo dynamic reigns.

The reality is that some friendships, including very close friendships, may currently be incompatible with where you are now. Letting those friendships go or taking a break can feel very heavy.

Not just because this is a person you love, with whom you shared so many good times. But because we are giving something up and we don't yet have something to take its place.

Grieving the relationship that once existed

We are letting go of something we cherish. Not necessarily the loss of the friendship itself - we don’t necessarily need to dramatically cut people out of our lives - but the loss of the version of the friendship that was familiar and comfortable.

Yet it is this quiet courage that is essential as we become our authentic selves. The ability to step into the unknown and let go of what no longer serves us. To risk losing a confidant, even if recently we haven’t felt truly supported or seen by them. Accepting the loneliness we feel as our social circle becomes smaller. Feelings of guilt at “hurting” someone we deeply care about. 

This is one of the hardest parts of this path. We need to grieve the parts of friendships we no longer have.

We need to get into a relationship with our loneliness and begin to accept - without attributing any fault or blame - that we may not get the support we need from the people who were once our closest confidants.

And we are faced with the prospect that there are simply fewer people in our lives at the moment who are available to provide that support.

Once we have made space for new relationships that reflect the current versions of ourselves, people will start to appear. We will encounter friends who are willing to “go deep” and still thrive with lightness and fun.

We will find companions who are committed to their own consciousness journey and stepping away from old patterns. We will start to build community and realize that we are not alone.

Older friendships take a new form

And we discover that our older friendships can still be there for us, even if they are in a different form. If we took a break, we may find that a new version of friendship is available. Perhaps different to what it looked like before, but still a beautiful connection that nourishes us.

Our friend may have seen our example and begun their own journey of self-inquiry, and we can begin to relate on that level. 

And if not, if the friendship does not resume, we can be grateful for the relationship we had and hold that person in our hearts, knowing that we acted with honesty and compassion. This is no failure, and nobody is to blame. These lessons are essential parts of our growth.

When we stop forcing ourselves to fit old shapes, something else becomes possible. We make room—for new ways of relating, for deeper connection, and for a social life that no longer costs us our integrity.

Journalling Prompts

• Are there friendships in your life that carry a tinge of obligation?
• Do you catch yourself performing in your friendships rather than bringing your authentic self?
• Are there any difficult conversations you have been avoiding in your friendships?
• What is the essence of friendships that you look for with new friends?
• How do you respond when loneliness arises?
• Where do you feel drained vs expanded in your friendships?