Grief is a stranger I have yet to meet. Or perhaps I have, though only as a distant acquaintance in the form of heartbreak, which in itself lacks permanence (a good thing, I suppose). Yesterday, over a comically large martini laced with brine and blue cheese olives (I like my martinis made with gin, dirty, and shaken—thanks for asking), I spoke to a boy about grief: what it meant for him to have lived through it, and perhaps more importantly, how it feels to continue living with it. 

At 36, I feel like I’ve experienced a decently vast range of emotions, and yet grief is one that has eluded me all this time. I guess I should be thankful. Some may even consider it a gift. Call me glass half empty, but I prefer to think of it as a curse that will simply strike harder than ever when it does. Grief is currently waiting for me—this much I am certain of—even though it remains on standby for at least the next 2-3 years, or so I hope. What I’m less certain about is whether it’s silly or even pitiful for it to come from the passing of a dog, one I call Guinness. The boy, with one hand on his wine glass, reached out to hold one of mine with the other. It isn’t, he said. I’m still not sure.

Guinness is a 13 year old border collie mix. Her mom was a majestic purebred border collie with grey and white markings. She looked like cookies and cream, and so went by the name of Oreo. One day, Oreo went for a walk and returned knocked up, completely unbeknownst to her owners. She got bigger and bigger each day, until finally one day, she could get bigger no more and ended up delivering a litter of six puppies - two light brown, two dark brown, and two black. We still don’t know who the father is, but whatever breed(s) he was, his DNA sure had a way of collaborating with nature to create perfect symmetry.

I have wanted a dog for as long as I can remember. Oreo's, shall we say, dalliance provided the perfect opportunity. I begged my mom tirelessly to let me adopt one of Oreo’s offspring. By the time my mom grew weary of my pleading and agreed, only one was still unaccounted for—a little black puppy with white markings on her chest that resembled an imperfect cross. She also had white fur on all four of her paws, which made it look like she permanently had on ankle socks. “She’s a little crazy, that one,” Oreo’s owner said with a small shrug, perhaps to offer an explanation as to why she was last to be picked.

It didn’t matter. It was love at first sight. I named her Guinness because she was black and white (doh). I also happened to be obsessed with all things Irish in my early 20s—something I blame on the Ireland football team’s improbable run in the 2002 World Cup, followed by an absolutely cracking St. Paddy’s Day spent dancing through the streets of Dublin, naturally with a pint of Guinness in hand. I even have live, laugh, love tattooed in Irish Gaelic on my arm - a decision I now chalk up to simpler, more reckless times.

Guinness became a part of my family at a time when I had just moved back in with my parents in Singapore after spending four years living alone as a college student overseas. It was a jarring adjustment, trying to figure out who I was and who I had become while returning to a country I called home yet barely recognized (oh hey there, Marina Bay Sands, when and where did you come from?). I was also nursing an overly romanticized heartbreak stemming from a long-distance relationship in LA that I was still (foolishly) holding out hope for.

So, I watched Guinness grow. I watched her learn how to navigate a brand-new world she had just been thrust into. I thought that by watching her, I might learn something myself about adapting to an unfamiliar yet increasingly familiar environment. Watching her teach herself to climb stairs—hesitant at first, then persistent—made me realize that fear is something that can only be conquered by doing.

And conquer together we did. Guinness witnessed both the intense joy and disappointment that came with every one of my careers. She saw friendships and romances come and go, licking in earnest the tears I shed each time (she likes the taste of salt, although I like to think she understands that salty liquid doesn’t naturally appear on human faces unless something else is wrong). She was even a part of my wedding party—in fact, the photo of her wearing a flower corsage around her neck is the only one I keep from that day given how short-lived my one and only marriage was.

Guinness has seen me in the throes of my deepest, darkest depression - a time I remember vividly and one I hope never to relive. It was Guinness who made me will myself up from the cold wooden floor I spent hours upon hours lying on contemplating the hopelessness of my life and its mortality. In the end, I didn’t have a choice but to get up to walk and feed her, lest I risked getting charged with animal cruelty or letting the same floor I lay on fester in filth.

Guinness and I no longer live in Singapore. Together, we have embraced new chapters of our lives, moving across the world to the US, and then moving cross-country from LA to Miami. Along the way, we have continued to create countless memories through our travels - from the Las Vegas Strip (with the Cosmopolitan easily being her favorite hotel) to the vineyards in Napa Valley and even the beaches of Costa Rica. 

According to scientists, Guinness is roughly 77 in human years. Today, she suffers from osteoarthritis, which makes it hard for her to climb stairs even though it was one of the very first skills she mastered. She also struggles to get up from the floor sometimes, though unlike me, it’s her body, not her spirit, that’s letting her down.

I don’t know how many more years I will have with Guinness, nor when grief will finally come knocking on my door. When Guinness was younger, her black fur was deep and coal-like, practically glowing with a sheen of youth. Today, it has faded to a smoky grey, like ash scattered over time, and each passing day etched into a growing number of white hairs.

They say that grief is just love with no place to go. I don’t yet know if that’s true. But as the boy sitting with me shared stories of the people he had lost, I realized one thing: love doesn’t vanish with grief, it simply changes. It softens, shifts, and slowly finds its way into what comes next.

P.S. If you enjoyed this piece, please consider (pre)ordering my first book - Digital Mavericks: A Guide to Web3, NFTs, and Becoming the Main Character of the Next Internet Revolution. It is a beginner-friendly guide to entering and navigating the crypto industry, filled with heartwarming stories of real-life builders and creators that I hope will inspire you as much as they inspired me.