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I’ve Had The Same Best Friend for 31 Years. Here’s What I’ve Learned About Friendship

We haven’t lived in the same city since 2002—but we’ve only gotten closer over time.
A photo of two women in brightly coloured clothing standing against a bar, used in a piece on long-distance friendship.

The author, right, with her best friend Shana. (Photo: courtesy Talia Leacock)

I was three and living in Barbados when I met my best friend, Shana. I’ve always been an unabashed extrovert, and I approached her on our nursery school’s playground and declared her my friend. Though Shana has always been deeply discerning and slow to trust, she immediately accepted my friendship. We’ve been inseparable since.

That’s not for lack of physical distance. When my family moved from Barbados to Florida just after my tenth birthday, it marked the beginning of a friendship that would span thousands of miles, multiple continents and countless flights. Through it all, our bond has remained unbroken. 

Shana is still the first person I call with good news (or bad) and I continue to be her go-to sounding board. We are partners in shenanigans—whether it's dancing our hearts out in the streets of Barbados during Crop Over or getting lost and finding adventure on our travels. And we have each other’s backs on serious things too. Together, we’ve built businesses, navigated heartbreaks and mourned losses.  

After 31 years, here’s what our friendship has taught me about life, love and womanhood. 

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Sometimes you just “click” with someone

My friendship with Shana has always felt predestined. Our fathers were acquaintances before we were born. When we were babies, they crossed paths and mused about having daughters the same age. They couldn’t have imagined that we’d find each other and forge a friendship on our own. 

Our instant bond has made me much more open to connections that just feel right. Ten years ago, an acquaintance told me that he thought I would get along well with his friend, Amanda, because we had very similar energies. A few months later, I met her through another mutual friend. My friend was right: I was drawn to Amanda just like I was drawn to Shana, and I immediately knew I had found a kindred spirit. Amanda is now one of my closest friends and I’m the godmother of her beautiful daughter.

Of course, I don’t expect to have lifelong friendships or partnerships with everyone I “click” with. But I’ve learned to welcome unexpected relationships, whatever their season or reason.   

Strong friendships take work

Today I live in Toronto and Shana lives in Barbados, but rarely a day goes by that we don’t speak. It wasn’t always easy to stay in touch. As preteens, we made phone calls using time-limited international calling cards. By our teens, we graduated to Skype and email. Today, it’s WhatsApp calls, where our conversations cover everything from the minutiae of what we ate for lunch to the insights and epiphanies from our individual therapy sessions. But we’ve always found a way to connect.

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We don’t have a deep conversation every day, but we commit to checking in regularly, even with a quick text or voice note; and when either of us is in crisis, we drop everything to answer the phone. That kind of commitment is one of the pillars of our friendship, and it’s become a practice I’ve applied to other relationships in my life. Remaining close to people despite distance, schedules and life challenges means putting in the work to not only stay in touch but to make that contact meaningful. 

True friends hold you accountable

Shana is my biggest cheerleader, but when I’m out of line, she’s the first to tell me. She doesn’t let it slide when I fall into bad habits or slack on working toward my goals. She’s also quick to let me know when I’m not handling conflict well. A few months ago, I made a mistake with a client, and I drafted an email to address the issue. After reading my draft, Shana asked me, in her signature direct manner, why I was over-explaining myself and grovelling instead of just offering an apology that reflected my genuine feelings. Her question stung, but she was right, as she so often is. 

I don’t like to be told I’m wrong—who does?—but I know Shana calls me out because she loves me enough to want me to be my best.

A great friendship sets a high bar for romance 

Accountability is only one of the many ways my friendship with Shana has shaped my understanding of love. Our friendship is also defined by support, kindness, consideration, honesty and a willingness to see and understand each other even when we disagree. 

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When I was married, there were times I felt frustrated that my ex-husband didn’t offer me these things as consistently as Shana did. Some might argue that’s an unfair benchmark. I disagree. That she’s loved me so well for decades is proof that I’m not asking too much, and I won’t lower that standard for future partners. 

There is no “right way” to be a woman 

Shana and I have lots in common, like our senses of humour, love of writing, obsession with fashion, unwavering ambition and propensity for tears. But we’re also different in significant ways. She wants to have kids; I want a hysterectomy. She’s adventurous; me, not so much. I’m a social butterfly; she’s introverted. 

We don’t judge each other for these differences. We just are who we are. Our friendship is a constant and beautiful reminder that women get to make our way in the world on our own terms, and we can go through life together, even if our paths differ.  

I consider myself lucky to experience a friendship of this depth and breadth. It is a gift to have someone in my life who has been a lighthouse when I felt lost in the darkness and whose growth I have been able to witness and support in return. I cannot wait to see the joys and lessons the next 30 years of our friendship will bring. 

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