The Charm of Drinking Alone

On Dressing for the Evening and the Hope of Finding Connection in a City that Never Sleeps

The Loft at Waldorf Astoria is the usual place I come to every week. Not every day, mind you. But every week.

Perhaps it is the fact that the spot sits on the 56th floor, among the thirty tallest buildings in town — offering the full, wide landscape of Bangkok, especially at dusk. You see the LED lights everywhere. From the vibrance of Ratchaprasong, full of traffic jams and malls, to the end of the horizon that vividly gives you the feeling of the city that never sleeps.

Cocktails are probably the other thing that brings me back again and again. As a bar recognised by Tatler, the classics I love — Americano, Negroni, Martini, Whisky Highball — have never disappointed me.

Though lately, since every concierge, waitress, and bartender remembers my face and the dinner attire I wear for the place, I have taken to asking the bartenders to make something unique, something that fits my mood. My last drink was a Bangkok Sling. Normally it would be the Singapore Sling, which uses pineapple juice. This one used guava, with a spiced garnish, to make it Bangkok in his own interpretation.

That is the charm of cocktails, I suppose. The art of making a drink to tend someone’s soul, in whatever mood they arrive in.

But the true highlight — the reason I am addicted to this place, and to many great cocktail bars across Bangkok — is the ambiguity of it.

You never really know what you will see, or who you will meet, that evening.

The experiences vary.

From witnessing a shouting match that almost turned into a fistfight, at the very level of five-star hotel prestige. To the economist who also adored Martinis and James Bond, and ended up in conversation with me until midnight. To the elegant lady in a black dress who walked over and asked me to take a photograph of her, and who later became a companion hard to forget — an orchestra performance one night, an afternoon museum walk another.

Which has led me to a realisation.

Perhaps the reason I am so eager to put on my evening attire — not necessarily a dinner jacket, but something appropriate to the mood and context of whichever bar I intend to visit — to put on a good fragrance, to walk into the night, to sit at the bar, to sip a well-made drink, and simply be there, alone — is the desire to make a connection, in a metropolis that tends to get lonelier every single day.

A big city. Especially Bangkok, where lights, neon, and the sound of automobiles and motorcycles run at all hours. Even with millions of lives living in the very same city, to find someone to simply sit down with — to have an inspiring conversation, to connect at a substantial level beyond a shallow exchange on social media — is rare.

And putting myself alone at the bar allows me to deal with it.

Not perfectly, for sure. Some nights, it gets even emptier than before.

But many times it has given me unforgettable evenings. And a small hope that real-life connection — without mutual followers, without the algorithm’s introduction — is still possible. Even if it becomes harder and harder to find.

So: the evening, in modern evening attire.

Think of a midnight-blue worsted wool dinner jacket with a satin shawl lapel — the kind Cary Grant wore in To Catch a Thief, or Sean Connery in Dr. No. But forgo the bow tie. Forgo the galon-striped trousers. Keep only the jacket, as a reminder of the ritual, of the sophistication of wearing one to a place that still deserves it.

Even if no one else is wearing it anymore.

And then the place itself. The 56th floor, carrying that prestigious Manhattan name. The gold shimmer of the Art Deco interior.

I think it is a charm that nothing else replaces. Especially if you go alone — and see what the universe might hand you.

Something, or someone, to observe. Or to engage with.