She’s over by the bar talking with a friend.  James (the brave subject of this story) decides he HAS to meet her.  He tries to remember a few tips he’s heard about approaching women, and walks over to her.

He moves through the crowd, and comes up behind her and taps her on the shoulder.

“Hi, I’m James.  I was just standing over there and I wanted to come say hello to you.”

She has to stop her friend mid-story to reply, “Oh, hey.  What’s up?”

“Um, so how’s your night going?”

“Good!  We just got here a little while ago.”

James has to concentrate on not looking at the floor, because he’s feeling nervous and not sure what to say next.

“So… do you like this bar?  I come here a lot.”

“Oh I’ve been here a few times, it’s pretty cool.  Oops – looks like it’s our turn to order drinks.  Nice to meet you…”  she says as she turns to follow her friend up to the bar.

He stands there feeling stupid and awkward.  He scratches his neck and goes back to stand with his buddy.  As he’s walking he realizes that he didn’t even get her name.  Damn.  Why didn’t he say something funnier?  Why couldn’t he just relax?

This kind of thing is so painful that you want to just find a corner and stay there.  It can put you in a bad mood for the rest of the night.  It’s happened to most of us before, and it’s the main fear preventing guys from getting out there.

There’s got to be a better way!!

I’m going to show you a few ways to start talking to a woman in a social bar setting.

When was the last time you met an attractive girl in public, out of the blue, having exactly zero prior connections with her, and had a conversation?  That kind of thing can be RARE.

It takes a special kind of courage to waltz up to someone you don’t know — but who you’re attracted to —  and start talking.

This can be so hard.  It’s like you’re literally forcing yourself to put one foot in front of the other and move in her direction.

Picture yourself in the scenario above.  What would you be thinking about?

  • “I have no idea what to say when I approach women.  Even if I come up with something beforehand, I just forget by the time I say hello.”
  • “I feel like I’m intruding on her night, like she really doesn’t need me bothering her.”
  • “She’s going to see me walking over, and it will be totally obvious that I’m about to flirt with her.”
  • “The women I want to talk to always seem to be hanging out in groups already.  It would be so weird for me to walk up and interrupt them to introduce myself.”

The problem with this situation is not that you lack the confidence or charisma to pull it off, but that by trying it this way you’re screwed from the start!

Actually, seeing someone you like at a bar and then making a beeline toward them IS kind of weird.  Especially if you don’t happen to feel like the world’s smoothest conversationalist.

I’m going to give you a subtly different way to picture it.  I’ll show you how to avoid using sheer force of will to get out there and meet someone you think you’ll like.

How to make conversation with a perfect stranger – and make it feel natural

You’re a lot more likely to make a good impression if you have a positive mental image of how your interaction will go.  If you can reasonably expect her to react well toward you, you’ll feel less afraid of an outright rejection.

So here are 3 steps you can use to feel more relaxed and become awesome at breaking the ice with women in bars:

1. Create a natural opportunity for the two of you to start chatting

Instead of a direct approach, casually position yourself so that you have some other reason to be near a woman you’re interested in.  I find that it’s best if you’re off to her side facing in the same direction rather than face-to-face because it’s more open to the room.

Then take a pause.  You can get her attention when you’re ready.

For example, you could try…

  • Waiting for a drink at the bar
  • Watching while she waits to hit a shot during a game of pool
  • Looking through songs on a jukebox
  • Watching someone else sing a karaoke song onstage
  • If she’s sitting at the end of a table, and the tables are tightly spaced: sit yourself at the end of your own table, next to her.  You’ll probably need to be with a group here.
  • Watching other people dance to live music, if the place is small and not too loud.

This 1st step communicates one simple thing: when you talk to her, it will feel smooth and natural. She will unconsciously feel more comfortable because she doesn’t feel like you sought her out to execute a “plan of attack.”

You’ll be able to relax yourself before you have to say anything.  You can channel your inner Fonzie and be cooool, Ringo.  It might actually help to observe for a second because then you can…

2. Use the environment and context to decide what to say

If she is the smart, good-natured girl you hope she is, you can say practically anything as long as it’s done with good humor and a warm smile.  There’s no need to try and come up with a super witty line.

You can make this really easy on yourself by starting with a topic related to something you’re interested in.  It’s less likely that you’ll flounder if you search the ol’ noggin for stuff that you think about normally.

Here are some specific things you could say, based on the examples in #1:

  • Waiting for a drink at the bar…
    • “Ever had a special cocktail here?  I’m looking to try something new.”  Or… “You know, I hear they smoke the ice here for extra flavor.  Interesting, huh?”
  • Watching while she waits to hit a shot during a game of pool…
    • “You should bank the 2 ball off of that wall and combo into the 6.  I’ve seen how good you are at this!”  Or… “I love playing pool here, somehow the felt on the tables is still like new.”
  • Looking through songs on a jukebox…
    • “I’m just looking for Taylor Swift – I don’t care what you say, she makes great music!”  Or, “This is a very important decision, so choose wisely.  The whole bar is going to listen to the songs you pick…”
  • Watching someone else sing a karaoke song onstage…
    • “Wow, this guy really knows how to get the crowd going!”  Or… “Are you going to get up there?  Do you have a go-to song choice?”
  • If she’s sitting at the end of a table, and the tables are tightly spaced: sit yourself at the end of your own table, next to her.  You’ll probably need to be with a group here…
    • “I wonder if the artwork on the walls here was done by someone local.  I’ve never seen anything like it, have you?”  “ Or… “Hey, do you guys want to play a game with our group?  We brought cards.”
  • Watching other people dance to live music, if the place is small and not too loud…
    • “Where did all these partner dancers come from?  They’re so good!”  Or…”I didn’t know they had bands here – these guys can really play.”
Smoked ice… the coolest of all the ices.

Notice here It would have been pretty hard to come up with any of these starters before actually being there.

After a little practice you’ll stop wondering if you should prepare your conversation starters in advance, and instead just enjoy being in the moment.  You get to have a little more fun with it!!

This 2nd step communicates the following:  You are present and in the moment.  You have interests that you care about, and that you can probably use in the future to create a fun time for the two of you!

She will NOT feel like you sit at home after work doing nothing, or that you are going to be stuck in your head talking with her.

Here’s a recent example from my life:  I was at a bar that served drinks to-go, and the bartender handed this girl her beer in a clear cup with a lid, like for an iced coffee.  I joked with her, “So are you going to drink that beer through a straw?  Because I can get you one!”

She looked at me and said, “Of course not!  That would be disgusting, I’d never drink beer through a straw..”

We had a good laugh and just like that, the ice was shattered into tiny pieces!

3. Introduce yourself, continue the conversation for a bit, then leave her some space

After going back and forth for a little while (maybe even only 60 seconds), now is a good time to introduce yourself.  Maybe extend your hand for a friendly shake.

You can continue chatting for as long as it’s comfortable and fun for both of you, but this is where you want to be really perceptive of her body language.  She may feel like returning to her group of friends, or any number of reasons to stop talking for the moment.

She might shift her body to face away from you, or her eyes might start to wander.

This is okay.  If your short conversation with her felt pretty fun and warm, awesome!  Leave her some space and occupy yourself for a bit before reconnecting.

You can do this smoothly by simply saying: “Great talking with you!  I’ll see you later, OK?”

This 3rd step communicates the following: You are confident.  You are comfortable in your own skin.  She’ll see that you don’t NEED to immediately turn this into a romantic connection.

You’ve developed a little bit of rapport now, so the next time you bump into her, you can just start chatting again with a simple “Hey, how’s your night going, [Her name]?”

Now let’s see what happens when you stack the deck in your favor a little bit…

Here’s what it looks like when you implement these ideas

Our friend James has had a good week.  He finished his to-do list at work and successfully cooked a delicious risotto recipe he has been wanting to try for dinner.

This Friday night, he has a couple of friends in from out of town and they ask him to pick a place where they can all meet up.

They decide on a whiskey bar that has a live music room where bands play sometimes on the weekend.

When everyone arrives, they go to the side room where it looks like a band has just set up.  A pair break off for a minute to get drinks at the bar, when James notices a cute girl at a table near the back – she has just taken a sip of her cocktail, but visibly puckers and squints her eyes.

She’s dressed well in a simple, flattering dress and necklace.

James leads his friends to the table next to hers.  After they spend a minute catching up, he decides to talk to this intriguing lady to his right…

With a chuckle, he asks, “Enjoying your drink?  I find that the bartenders here are particularly skilled.”

She replies, shaking her head, “Oh God no, my friend got me a vodka and tonic without knowing that vodka is not my thing.  I mean, we’re at a whiskey place!”

“I’m so sorry to hear that, I wouldn’t do vodka here either.  I always end up getting something with Blanton’s – do you like bourbon?  I’m James, by the way.”

“I’m Laura, nice to meet you (extending her hand).  Sure, I’ve definitely had that before,” she says. “I’m so glad they have it here!  Excuse me, I think I’ll take your advice.”  She hurries to the bar.  By the time she returns, the band has started up playing some energetic blues rock.

After a couple of minutes chatting with his friends, James taps Laura on the shoulder.  “I love this kind of blues music.  Kind of glad they aren’t another cover band like the last time I was here.”

“Oh my gosh, I love it too!  These guys are playing pretty well.  I went to Chicago a couple of weeks ago to see some live shows, like Buddy Guy.  It was so cool.”

Excited that they have found some common interests, James relaxes his shoulders and smiles.


Alright Casanova, now it’s your turn to take a chance at meeting new and interesting women.  Pick one of these tips and take it for a spin!

If you join my email list, I can send you a quick cheat sheet with these exact scripts and more, for when you’re getting ready to practice in the real world.

Or hop down to the comments below and share your success –  I’d love to hear it.  🙂