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Drake Came Into My Bar and I Made an Ass of Myself

Lessons in setting intention

Drake sitting in a lounge with friends

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Nobody told me opening a bar was a bad idea. Actually, everybody told me that it was a bad idea. My father said “son, don’t tell anyone you own a bar, people get shot in bars.” So ok, it’s a cocktail lounge. A bar/lounge/restaurant.

My partner Steven and I decided to hide the lounge behind a coffee shop front end, making it a speakeasy with a cool hidden entrance. I’m not going to link or name it, that’s not the point of this post. Wait, I think I just lost all credibility. This guy doesn’t have a bar-lounge-speakeasy! He’s just making shit up.

Ok ok. Coffee Oysters Champagne in downtown Toronto. It’s a beautiful place, you know how I know? Because a friend of my sisters who came to visit soon after it opened said to me, “Sanjay, don’t take this the wrong way, but this is so much more than I thought you were capable of.” Yup, you and me both sister.

So one afternoon, our coffee shop manager comes and finds me in the back, saying “Sanjay, may I?” That’s cool bar-lounge-venue speak when interrupting another staffer or manager. I said “what’s up?” He says, “You’re a Leafs fan right? You might want to come out to the coffee shop, but come quickly.”

I jogged to the front of the lounge and peeked through a door into the coffee shop, and what to my wondering eyes, but sitting there having a hot brew are Auston Matthews and a teammate who might have been Mitch Marner, I’m not sure because I immediately ducked my head back into the lounge and said to my colleague, “Dude! That’s Auston Matthews! Dude!”

He asked me, “Aren’t you going to say hi, like hey I’m the owner or something?” I said, “No way. He’s here to have a coffee, not be pandered to by some idiot who thinks he’s a big shot because he owns a bar/lounge/bistro.”

He said, “At least tell him about the Speakeasy?”

Gaining confidence, I replied, “No. We don’t tell people who don’t ask. No need to make an exception. But boy is this a great story to tell my friends.” And then to my regret, I walked back into the lounge and started texting my friends. Because what I SHOULD have done is at least saunter past their table in the coffee shop and photo bomb them or something. Then I’d have a way better picture for this post.

On hearing the story the next day, one of my friends, Kevin, said to me, “Why didn’t you talk to him? You should have talked to him. He’d appreciate it, you’re the owner after all.” Kevin probably doesn’t know this because I’ve never told him, but I respect the hell out of him and I took his advice to heart. Auston Matthews never came into the shop again, but.

Drake did.

Wait, it gets better. Drake actually came into the speakeasy and it wasn’t even the first time. It was a few weeks after my Maple Leafs encounter and Drake brought an entourage into the lounge from an even more secret back door, where our staff had ensconced him in a curtained off private booth, and he put a couple of bodyguards outside to warn off the riff raff.

With Kevin’s advice echoing in my head, I saw this all happening and after completely ignoring Drake the last time he had come in, this time I decided I was going to say hello. I imagined him smiling and shaking my hand, telling me what a great place we had, maybe inviting me to sit down for a few minutes. I imagined.

So I walked up to one of the guards and said, “Hi, I’m the owner, I just wanted to say hello to Drake.” They graciously opened the curtain, and Drake looked up at me with a quizzical expression. I said, “Um, hello, my name is Sanjay, I’m one of the owners here and I just wanted to say thank you for coming in, we appreciate your business.”

He smiled uncomfortably, accepted my outstretched hand, and mumbled something like “Sure sure, thanks.” Then he turned away from me to resume the conversation I’d interrupted with his companions. I was left standing there while everyone ignored me, so I quickly backed out of the booth and went and hid in another room where I could gather my thoughts.

I felt like a complete idiot. Well what did I think his reaction was going to be? I’m not a Drake fan, I’m not going to tell him how much I liked pineapple fruit or whatever that song was. I’m sure he’s thinking “Geez, I hope this dork doesn’t ask for a picture. Can’t a guy just have a drink?”

Sorry Kevin, it was good advice, but you probably thought you were giving it to someone who could think of something interesting to say. Sorry I let you down.

I want to make it clear here, Drake could have behaved differently, but he wasn’t the problem. I was. I didn’t approach him with a plan, and I especially didn’t approach him taking into account what might be going through his head. I had no intent other than a vague sense that I should, and that my status as an owner somehow offset Drake’s status as a celebrity. The difference was — he was the customer.

It was a good reminder that we move through life with intention. Make friends with people you like, not people you think you need. Think about what the other person is thinking. Taste your words before they come out of your mouth. Don’t spam people. It doesn’t work and it lowers your value. Be kind.

Drake hasn’t been back since that misstep. I tell myself it’s because we don’t play hip hop at my bar-lounge-grotto, but I know the truth. He doesn’t want to run into that dork owner again.

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