As I raised a glass of sake in a limo with a group of Japanese businessmen whom I met an hour earlier, heading to an undisclosed party that they assured me would be a good time, I thought, “Damn, I love drinking with strangers!”
I do. To me, it’s a sport, like hunting, but without the senseless death and ecological destruction. I’m not talking about chitchatting as you wait for your table at a restaurant. I’m talking about digging down deep and engaging, connecting and, if things go right, heading out to another venue for additional shenanigans. Think of it as a social one-night stand. Everyone should do it at least once.
The key, though, is to start early. Happy hour is ideal. Start too late or after too many drinks and, like me — another story, another place — you may end up in some drug den in Boston, praying your Uber driver won’t be scared off by the sound of gunfire.
So start early and go to a bar you’ve never been to. Not a club or a lounge. Those places come with particular intentions. Bars are for drinking, and the people who love it. Also, if this night goes sideways, you don’t want it all to have begun at your regular watering hole and risk having to explain shit to your favorite bartender.
Also: You have to go alone. You don’t want some friend acting as the voice of reason and talking you out of a potentially good time. And don’t worry about looking like an alcoholic. In my experience, alcoholics are typically drinking with friends.
Now grab a seat at the bar. I’m a fan of the seat at the elbow or next to the server station. This will keep a constant flow of people looking to order and get yourself a drink. Beer. Whiskey. Vodka. Tequila. Or a specialty cocktail designed by the establishment.
That’s the list of things you’re permitted to drink. No wine. No one has ever kicked off a rager with “Let’s bust open some Chardonnay and get this muthafucka crackin’.” And, oh yeah, stay off your phone. You get to updating your status or staring at your watch like suddenly you need to know the time of day and strangers will think you’re waiting for someone. Thus, the invitation to join them will never come.
The “them” in question? Your new crew. Finding your crew is the most crucial part of the night. Avoid groups of coworkers or you’ll find yourself faking interest in their ramblings about how everyone hates “Jim in accounting” before they part ways early, when they run out of work gossip. Remember — they’re not friends. They just work together.
Tourists are great. European ones are the best. I kicked it with some Irish tourists who came straight from the airport and plopped their suitcases down by the bar, which turned out to be a smart move. At our third bar, one of them disappeared into the bathroom and emerged in different clothes, explaining he threw up on himself and didn’t want to ruin the night smelling of Guinness.
The group talking loud, egging their friends to stop nursing their drinks, is the one you want to roll with. Three is the perfect number of people. If it’s two, you’ll often find yourself on the outside of the conversation. Same with four. Anything more than four is a field trip you’ll be wishing you hadn’t signed up for. Three is just right.
Once you find your desired group, don’t overthink the approach like some douche trying to articulate the perfect pickup line. Keep it simple. Make mention of the music in the bar or the cocktail they just ordered. Don’t worry, things will move quickly. At first you’re chatting, having some laughs, then another round, and pretty soon you’re sharing secrets. It’s amazing what people will share with someone they will never see again.
When Brooke from Memphis whispered she had just discovered her boyfriend, who was only a few feet away, was cheating on her with a man and she liked the idea of the guy who’s fucking her getting fucked by a guy, I just nodded. I didn’t judge. She was sharing a secret.
You also have to share a secret. It bonds you with the group. They have a history, and now they’ll have a piece of yours. Make it something you’ve never told anyone. Once I shared I had been caught stealing at Best Buy and the police officer was so stunned I had stolen a John Coltrane CD collection to listen to and not sell that he pulled over and told me to get out of his car. I had never told anyone, but the group of strangers laughed, and I exhaled. Sometimes your secrets are easier to share with strangers than with friends.
Ask them what they have planned for the night or where to hang after happy hour. If they’re not getting the hint, ask to join them. People never say no. It’s why serial killers find victims so easily. Probably not the best example, but it’s true.
Once they lay out the itinerary, the answer is “Hell yeah, let’s do it.”
That phrase expresses your unwavering commitment to the unknown. Saying no isn’t an option, unless it may result in death, incarceration or permanent scars, and the last two may be worth the risk, depending on the circumstance. “Yes” will take you to strange places, talking to people you never expected.
Those Japanese businessmen were a blast, but I informed them a night of drunkenness here ain’t officially over until you’ve soaked up the giggle juice with pancakes served in a little slice of Americana we like to call Denny’s. Two bites into their Grand Slam breakfast, they agreed. I had never felt so American.
When you decide you’re done, call it a night. Maybe you’re tired or you’ve run out of money or shit got weird when you were invited back to the hotel to get high or have a foursome or, as I assumed, both. Connect with your new “friends” on Facebook if you want, but drinking with strangers isn’t about making friends. It’s about making a connection that doesn’t involve a “Like” button. Social media has us more connected yet lonelier than ever before, and I would much rather chat with a stranger in a bar than text with a friend from my couch.
When you’re old, unless you’re a Kardashian, you’re not going to remember the number of likes you got on Instagram. But you’ll definitely remember the night you hung out with that guy who was banned for life from Best Buy, whom you drank with and ended up at Denny’s, watching the sun come up.
