
A couple of weeks ago I found myself on a last minute trip to Montreal. I had a lot of vacation time left and didn’t want to spend it lazing it around my apartment, plus I had a Via Rail coupon I needed to use before it expired at the end of the year.
Normally when I travel I have some kind of rough itinerary, but this time I really only wanted to see friends I haven’t in years, and Leonard Cohen’s mural and grave. Maybe bravely order a coffee in French.
November isn’t a kind month in the northern hemisphere; and as it turns out, also not a particularly ideal time for visiting Montreal. I tried to book some sightseeing tours, only to find they were shuttered until spring. I had a lot of time to wander, but the weather didn’t want to cooperate either. It rained most days I was there, and when the sun did peak out, it was bitterly cold.
Still, I hadn’t been in the city for eight years and hadn’t seen those friends since then too. I was a bit nervous. Would they think I’ve aged brutally? Would we still have a lot to talk about?
My first night there my girl friend met me late afternoon and thankfully, it was if no time had passed at all. After an early dinner, we wandered the downtown in the rain. Nothing felt familiar to me, despite having been to Montreal many times before. I don’t know if it was the darkness, or the turnover all cities have gone through since covid, but I couldn’t get my bearings. My friend gamely tried to show me how to follow the blue arrow on the maps app, but to no avail. I got lost whenever I was on my own.
The next day after attending an extremely loud Remembrance Day ceremony (they fired 21 actual cannon shots!!), I somehow managed to find my way to Leonard Cohen’s mural and a lunch with some colleagues, but not before walking the wrong way enough times to add multiple kilometres to my journey.
That evening a pal and his wife took me out for dinner and then drinks. Being a Monday night, not a lot was open. We found our way to a tiny bar on a second floor that had a handful of games. Some old pinball machines, broken skeeball, live action Pong and a claw game.
Hanging over the bar was a stuffed pickle. It looked something like this, and I was determined to have it.

I asked the bartender; who was also the owner, how I could get that pickle. He pointed at the claw game shoved awkwardly into the corner next to the pinball machines.
“You have to win it.”
He handed me a couple of tokens that came with my beer. Wanting to warm up first, I decided to test my luck on the ‘love machine’ which reminded me of a Simpson’s episode. It wouldn’t start. The owner came over to reset it. The game pronounced me ‘a passionate lover’ but the printer had long run out of ink and there was no paper either, so you’ll have to take my word for it.
Emboldened, I went to face the claw. Strangely the night before, my girl friend and I visited a store (?) that was entirely claw machines. We saw a man with a shopping cart full of plush toys, and asked him his winning strategy. He told us you have to find the toys that had more shape to them, like an alligator or dinosaur. They were easier to grip.
We thought he got to keep that entire cart full of plushies, but instead, he needed to turn them to trade for one larger stuffed animal. Based on how much he spent to win it, it seemed far more economical to just buy it somewhere. But I guess that’s less satisfying.
Now feeling like I knew the secret to defeat the claw machine, I looked for the toy that seemed to have the most edges. I figured if I won, I could ask to exchange it for the pickle.
After multiple failures and running out of tokens, I gave up in frustration and went to play the broken skeeball machine. The numbers had long since worn off and it didn’t print out tickets anymore. But the scoreboard still worked. I asked the owner what score I needed to win the pickle. He told me 450. My first roll was a 50 and I thought I was going to do it, like Rudy finally getting to play, or Michael Jordan’s flu game.
Instead, I missed all my other shots. And the owner was unyielding. The stuffed pickle remained tantalizing out of reach. He did however give me a pickleback shot for my birthday. And after some chatting, let me try some actual pickles had had brined himself, and a pomegranate molasses he’d made too (take that Bobby Flay).
I felt a kinship with those barely functional games. Sure, their shine was faded, the paint chipped and half the lightbulbs burnt out. And sure, most people have long since moved on to video games that look like slickly produced films. But they still stood proudly, if not a bit wobbly.
Like me, they’ve aged. But when you’re playing them, nobody is paying attention to that. Maybe there’s a lesson in there for me too.
The next day, and my last day in the city, my dinner plans got cancelled and I found myself with a free night. I briefly considered going back to the bar and trying to win the pickle again. But then I remembered I had no clue where it was, or even what it was called. And I knew if I returned, I’d ruin the magic of stumbling onto a place unafraid to be genuinely rundown and nostalgic in a time that’s so irony poisoned.
Sure, you can spend enough to fill a shopping cart full of stuffed animals, but sometimes it’s just better to accept futility.