How to Pick Up a Woman Wearing Headphones

I’ve wanted to write this article for quite some time, mostly because I like a good challenge.  I have to give kudos to the “Modern Man” who wrote this piece which I am reacting to here and putting in my own words. (Always have to give props when they are due, but I did put my own spin on this because I have some different tactics in comparing styles.)

I was once tasked with hitting on a woman who was donning head phones and rocking out to some sort of music at a bar & grill here in Miami Beach.

You know how society has changed, right?  Most everyone is multi tasking, has severe ADD, or just an iPhone addiction.  So finding women with headphones on is much more common today in comparison to years past.

But, don’t let that stop you from hitting on her and making a move!

Sure, you’ll get shot down a lot, and get some bad feedback at times, but being a guy who takes risks is what got me to where I am today – a man who can proudly say I’ve been getting laid on the regular for quite some time, even in the highly competitive Miami market.

If a woman is into you, she’ll oblige and take off her headphones and hear what you have to say.  If she’s not into you, she won’t.  But you don’t want her any way so what difference does it make at that point?

how to pick up a woman wearing headphones

Best Way to Approach a Woman Wearing Headphones in Public

First off, don’t be a creep and get really close to her.  Keep your distance, which should be about 3-4 feet from her.

Be confident, and smile a lot.  Women like men who smile.  Who wants to talk to a guy who looks all grumpy?

Something like “how are you doing?”  Or “is this seat taken?” are always good ways to start a friendly conversation.  If you want to do what I call a “distance holler” you can wave your hand to her from across the way, but it’s far from personal, and not really what I would suggest you do because I have a reputation to keep her at

If she gives you the cold shoulder, don’t press the issue.  Just let it be and take the clue she has no interest.  Nobody wants to seem like a pest.  Don’t be annoying.  In fact, if I make a move and she’s not interested, I say something like “I’m really sorry to bother you.”

We’re all about meeting people here, and while we know our forte is consulting people on finding the best places to meet one another online, we’ve got a little bit of advice for every topic that goes hand in hand with dating.  So whether that’s meeting in a bar, a coffee shop, or online, we’ve got two cents of advice for all those situations.  People meet all the time.  Things move at different paces, go different directions, and have their times and places.  Sometimes, you just see someone you MUST know.  It’s happened to me many times.  And unless I get married (fat chance) it’ll most likely happen again.

Don’t Make These Rookie Mistakes When Approaching Women

#1:  Don’t be nervous

If you want things to go smooth, be relaxed, confident, and cool.  Women normally like guys who are strong and confident.  Don’t be weak and show anxiety or any nervous tendencies.  That’s a big turn off for women.

#2:  Keep Your Eye on the Prize

Persistence is a serious thing here.  Be a persistent person in this critical time.  Sure, you may get an odd wave at first, but flash a smile and see if she will remove the head phones.  Their first response is usually being defensive, which means she’s going to do whatever it takes to NOT talk to you, versus talking to you right away.

#3:  Have a Topic of Interest Already in Mind

You need to have a game plan and know what you are going to say or that awkward silence is going to crush every chance you have at hooking up with her. (Well, let’s not race ahead, let’s say acquiring contact.)

#4:  Be Polite and to the Point

Get your two cents in, say what you want to say, and do it fast.  Remember, she just took off her headphones for you.  Be quick!

#5:  Be a Flirt

You have to show some interest, so making a funny comment or flashing smiles and winks is probably your best bet.  I always say that if I’m not touching a woman somehow within one minute of meeting her, it’s not “on.”  Do something to generate a high five and gauge her enthusiasm, (or lack of it) based on that reaction.




Tom Savage is a serial dater living in Miami Beach, Florida. In between pool parties, late nights, and an occasional day trading session, he likes to share his tips on meeting women online. You can contact Tom on this page.

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