Be Better Guys Tips on Drinking Alone in a Bar


Because I travel and I often do it solo, or I may stay at a hotel that may be different from others I’m traveling with (I’m loyal to Westins; try ‘em, you’ll see), I often drink alone at the bar. Going into a bar alone can feel weird. Usually, I go into bars with my wife, either for a drink before a show or to have dinner at the bar, something we love to do

But when I’m solo, and it’s too early to go to bed, and I’m done working, I’ll still go to the hotel bar. I’m not a TV watcher. Not in my room. Never turn it on. So I tuck in my shirt, throw some water on my face, grab a book or magazine, and head to the bar.

The key to walking into any bar alone is confidence.

If you stroll in with a sort of an “I have nothing else to do, and I know everyone’s looking at me because I’m alone” look, guess what? Everyone WILL look at you and wonder what your problem is.

Instead, walk in as you belong there like you’re looking for someone. Walk-in with confidence. Survey the scene. Find a spot at the bar, get a stool, and take it. I usually don’t put myself in the middle of a bar; I go for the end. I can watch the scene from there.

I usually sit down and make small talk with the bartender. If it’s a guy bartender, it’ll be about sports. If it’s a woman bartender (my favorite kind), I’ll ask about her. Been a busy night so far? Did you work a double? Whatever – just something to engage her.

Most women bartenders initially give me the usual disdainful brush-off.

Quick answers, no eye contact, just transactional. But some, not all, linger when you order that second drink. See, you’ve been hanging around at the corner a bit. You’ve been watching, maybe reading your mag or checking out the ballgame. But you’re also looking at the other folks at the bar. And that’s when you comment: “When are you cuttin’ that girl off?” or “You’d think that dude, with his whole scene, would go for something other than the Bud Light.” Something to engage. And sometimes, not all the time, you start to chat and the evening just got a little more fun.

I don’t ever go to pick up single women at a bar.

Once I tried, just for sport. I was in Dayton, Ohio, at a Mexican joint with a staff of ex-Hooters castoffs in tiny shorts and bottle-bleached hair. There I am in my business khakis and dress shirt, looking as square as their dads. So I tried to chat up a waitress, just for fun. Failed. No, imploded. Why? ‘Cause I’m not the pick up a girl at the bar guy and now that I’m married, I clearly haven’t improved any.

But I do like to chat up women bartenders, and in that, I have great success. I’m not a threat. And I have no interest in any extracurriculars. I wished I had when I was once in the W in Chicago, but I let it go because, well, I’m a wuss. And I’m married.

It’s still fun to go to bars solo. Just check out the scene, see what’s what, and if nothing else and the place is boring, and there’s no sightseeing to be had, so you had a sweet bourbon or glass of beer and read your book and enjoyed a little time by yourself. Hard to even get that these days, so you learn to find happiness in the li’l things.