A barstool conversation

By Caitlin Kelly


Grand Central Terminal; the view from Cipriani. What’s not to love?

Sitting at the bar is where I’ve had some of my best conversations — in Corsica, in Atlanta, in San Francisco and last Friday evening in New York City.

It was about 6:30.

Commuters were rushing to their trains north, to Connecticut and to Westchester, tourists, as always, posing on the steps and slowing rushed New Yorkers down as they raced for the 6:47 or whichever train was next.

Never get in the way of a New Yorker in a hurry!

I settled in at Cipriani , an elegant Italian restaurant in a balcony overlooking the station. I had a magazine and a Mr. C, a citrus-based cocktail. The bartender kindly plugged in my cellphone to charge it.

A handsome young man in a navy suit and white shirt, no tie, slid onto the stool to my left; a slightly older man with a head of wild black hair and oversized sunglasses sat to my right.

“How’s your week been?” I asked the man to my left.

He told me he’d just gotten a new job, and we toasted, clinking our cocktail glasses.

He seemed surprised I was happy to toast a stranger’s success. Why not? Who would be too churlish to deny him that pleasure?

It’s a big deal to flee a job that’s a poor fit for one you hope will be a much better one. Been there, done that.

That’s the beauty, I suppose, of being near the tail end of a long career. For someone only a decade in, every decision can still feel problematic because you’ve yet to make that many of them.

An investment banker, he admitted he didn’t much like the field, but — probably like many people, especially those unhappy at work — he had pretty much fallen into it. If you know anything about I-banking, the income is certainly seductive, but golden handcuffs are still handcuffs.

I urged him to start creating an exit strategy. Life is far too short to stay in a field or industry you really don’t enjoy, I said.

He looked surprised by my vehemence, and my insistence one could actually enjoy one’s work life.

We ended up talking for about an hour, sharing stories of family and work, of dating woes and East Coast snobberies, and the classic diss we’d both experienced: “Where’d you go to school?”, a tedious sorting mechanism. (The only correct answer being the coy, “In New Haven” (Yale) or “Providence” (Brown University) or another of the Ivy League.)

“I’m strapping, right?” he asked me, at one point. He was, actually.

It was a bit awkward to be asked, even though the answer was affirmative.

He was a little drunk.

It made me a little sad.

He was single, and just under half my age, a fact he finally realized but managed to handle with grace.

We had a good conversation with lots of laughter, a few of of life’s more painful challenges and a few high fives.

I like how the right bar and a drink or two can connect two strangers companionably for a while.

(Just in case, though:

  1. Make sure you don’t get drunk; stay safe!
  2. Make sure no one has access to your drink except you (beware someone dumping rohypnol; i.e. getting roofied.)
  3. Make sure you feel 100 percent comfortable with the tone and content of any conversation. If not, move or leave.
  4. Make sure you can leave quickly and safely, if necessary; trust your instincts.)


Do you ever sit at the bar?

Do you ever talk to strangers there?

19 thoughts on “A barstool conversation

  1. I generally don’t go to bars, sadly. There are no good ones near me, and even in college, where half of High Street is bars, I didn’t go out that much, just for drinking holidays like St. Patrick’s Day or Cinco de Mayo, or special occasions like my 21st birthday or senior pub crawl. It’s just simpler to have the one drink at home when I’m in the mood. Saves money, anyway, which is big for me.
    Still, it could be a setup for a novel someday. Who knows?

    1. Well, clearly I enjoy them. I don’t spend tons of time there, but it’s a good place to meet a friend without having to clean up my apartment or feel like I have to prepare a meal.

      It also really depends a lot on the bar; some are just gross, noisy, TVs-dominated and generic, and some are fantastic.

      The NYT just reviewed this book today…

  2. No not really because one drink and I’ll be dancing on the bar! šŸ™‚ I’m a lightweight when it comes to alcohol! I would probably hang out at a beach bar though, with friends. I wouldn’t feel comfortable going alone.

    1. Interesting. I always have a book, newspaper or magazine with me and happily sit and read, eat,drink. I’ve done a lot of travel alone and it’s less lonely sometimes to sit at the bar than at a table.

    1. Thanks.

      I was a bit shocked that — single — he felt so locked in already. With that kind of income, you can create enough cash to get out. But then, that much income is very seductive.

  3. Never bars….but I walk my dog twice a day, and I can relate to that type of encounters. People have told me much about their lives, while letting our dogs play together.

  4. In a rare deviation from those warnings from my youth (Never talk to strangers! Eat your vegetables! Always say “please” and “thank you.”), I often chat with strangers…but not in bars. I’m often concerned that (especially men) might get the wrong impression. I’m 59 and not nearly as alluring as I used to be, but I still have that “something” that men find attractive (or so Philip tells me, like, ALL the time!). Maybe he’s the only one who can’t resist me and he’s “projecting!”

    I am rarely alone when I go out to restaurants and bars. But while walking my dog or standing in line at a store, I start up conversations just to be friendly.

    I suppose there is something about alcohol that “lubricates” a conversation.

    1. I hesitated to add that warning at the end of the post — but I know how to do it safely and have never had a problem with a creep or felt scared. But I’m also very used to chatting up strangers of all ages and genders in my work.

      It’s interesting — guys either freeze me out because they think (get over yourself!) I’m hitting on them, or they’re quite friendly and chatty. I don’t make a habit of this, but sometimes it’s fun and enjoyable. I’m still FB friends with the guy I chatted w in Atlanta about 6 yrs ago (and we are both happily married.)

    1. That’s why I said it to him — he’s making good money and with no family commitments and huge mortgage to lock him in. Getting out is a lot easier under those circumstances. Nothing is sadder than a work/life wasted in needless, escapable misery.

      I get paid to talk to strangers! Much of the time, I enjoy it. Sometimes, though, I withdraw entirely to recharge.

      The worst than can happen? They’re aggressive (ugh) or boring (double ugh.)

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