How to talk to someone sitting alone in a bar

Have you ever wanted to talk to someone sitting alone at a bar? It’s not as hard as you think. Just a mental hurdle you need to jump. Here are three easy steps to starting a conversation. But first, a story.

Last weekend my friends and I were out at a Scottish bar. Drinks, live music, and servers with sleeve tattoos wearing kilts. My friend Kaylie, a woman in her 20s, spotted “a handsome dude” sitting by himself at a two-person table drinking a beer.

“What’s so handsome about him?” I asked.

“He looks like a like a lumberjack from the future,” she said.

“Okay, weird, but whatever then go talk to him,” I said.

Kaylie’s eyes widened. “Oh, I could never.”

This is a common problem for most people. Approaching a stranger sitting alone can be daunting, but it’s not impossible.

At one point in my life, I just stopped carrying about what other people thought of me. I stopped caring about rejection. I stopped caring about how much money I made. About what type of car I drove, etc. Maybe it’s part of aging. Maybe that’s why you hear old people fart so much. Maybe they just stop carrying about being embarrassed.

And that’s kind of what you need to talk to someone sitting alone at a bar. You must be fine walking up to them, striking up a conversation, and then getting asked politely asked to bugger off.

Okay here’s the situation.

You’re at a bar. There’s a total stranger. Guy or girl it doesn’t matter. They probably have a drink and they’re probably on their phone. How do you barge in on that and strike up a conversation?

Well, it’s a lot easier than you probably think.

WHATEVER YOU DO, DON’T DO THIS: Even if they look bored, don’t say, “You look bored.”

Most people aren’t going to respond to that. What are they going to say? “Yes, I am bored because I am a total loser, thank god you rescued me from this boring hell hole, I don’t even know why I’m here.”

No.

What they’re going to say is, “I’m not bored,” and then you’ve got nothing. They sunk your leaky battleship. Now you’re adrift in shark-infested waters and your radio is broken. “Uhhh, okay no worries.”

What was your objective there? To find out if they were bored? Why? Of course they’re probably bored. They’re sitting alone at a bar while everyone else is having fun with their friends.

But they might not be bored. They might be just fine sitting by themselves because their mother just died and they want to be alone.

If you want to sit down and talk with a stranger then you need to figure out why they’re at the bar alone, and then put yourself in their shoes.

Imagine it’s your one night off this week and you had plans to get dressed up and hit the town. At the last minute, your two best friends bailed because they both tested positive for Covid. Being the party-starved person that you are, you decide screw it, I’m going out anyway.

But once you get to the bar you realize it’s a lot harder to have fun when you’re by yourself. So, you sit alone at a table and watch everyone else laugh and chat with their friends. Wouldn’t it be nice if a cute stranger walked up to you and struck up a conversation? Wouldn’t it be nice if they were fun and interesting and then invited you to hit the dance floor?

Maybe!

Or maybe you’re fine just sitting there and chatting with them at the table.

Regardless. The number one rule of talking to people sitting by themselves is you need to establish why they’re there.

“I just broke up with my partner, and I wanted to drink alone.” – Leave them alone.

“My friends ditched me, but I wanted to go out anyway.” – Jackpot.

You know how easy it is to talk to your friends? You can replicate this with strangers. At the bar you wouldn’t turn to your friend and be like, “So, it’s nice weather we’re having lately, don’t you think?”

You’d turn to your friend and say, “This music is sick, but I wished the dance floor was bigger.”

One of those two is a conversation starter, and one of those is lame.

Don’t be lame. Be friendly. Talk to strangers at a bar like they’re a friend. Maybe one you haven’t seen in a while and you want to catch up.

“What’s new with you?”

“Anything exciting going on?”

“What are you working on?”

“Are you building anything cool?”

“Do you think that dude with younger girl is her dad, or her boyfriend?”

Personally I avoid the, “What do you do?” type of questions. If I’m at a party, I’d rather ask someone, “So who do you hate here?”

Once you’ve been chatting a bit, and you’ve figured out why they’re at the bar alone, and yes they do appreciate your company, then you can invite them to join your friends. If you’ve got a table, ask them to come over and join it. Or maybe join you guys on the dance floor.

Remember, people want friends. Friends are fun. Earth can be a lonely place if you don’t have friends.

So, to sum it up, here are the three easy steps. Remember, to act like you’re a friend, not some creepo who wants to talk about the weather.

1. Establish why they’re at the bar alone. If you were in their shoes and would want to be left alone, leave them alone. If you’d want someone to hang out with, continue talking.

2. Engage in friendly conversation. Stuff you’d talk about with your actual friends. “Did you see the new Top Gun movie? What’d you think?”

3. Ask them if they want to join your group at the table, bar, dance floor, whatever.

Step three can be skipped if you get their phone number. That’s why you went over there right? You were attracted to them. Don’t be a wuss. Ask them what social media they use and get that. You can always chat and ask them out later.

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