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A blog about dating, meeting people, being social and everything in between.
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How to Flirt with a Stranger

Posted on 06/13/2007 in Dating Tips by Matt

I've got a thing for baristas, I can't help it.  Unfortunately finding a segue from "tall americano" to "HOLY CRAP YOU'RE HOT" isn't as easy as it might seem.  Flirting with a stranger is undeniably daunting: you risk rejection, embarrassment, or just plain feeling creepy.  It's not hopeless, however - there are ways!  Below are a few useful tips for bridging the gap between casual and flirty.

Incite a positive emotion, laughter is usually your best bet.  If there's one sure-fire way to make someone instantly like you it's to make them laugh.  You can flatter them, invoke curiosity, or simply be engaging - but being funny is still the most tried-and-true way of getting a positive reaction from someone.  Compliments and flattery can be interpreted in a variety of ways, laughter can't. 

Find something common to rally around.   Did you both just bear witness to an overweight, dirty pigeon taking a mid-flight dump on a well-dressed pedestrian?  Fantastic, now you've got something to talk about.

Avoid the jaded. Waitresses and bartenders are good examples of who not to hit on. They're usually just trying to make a living and whatever cleverness you've got up your sleeve isn't something they want to hear.  There are always exceptions, I've met plenty of people who work in customer service who enjoy the interaction, but generally speaking it's a lot harder to make an impression on someone who has probably heard it all before.

There's strength in numbers.  Having friends nearby lessens the likelihood that you'll look like a socially inept weirdo.   I don't recommend having your friends right next to you when you make your move, but having them in the background always helps   ./friends &  * 

* if you got that joke it's either really sad or really, really awesome..

Mind the body language.  Don't cross your arms or avoid eye contact, try to appear welcoming and sincere.  Keep a close eye on their body language as well, if they're interested you'll know.

Take it easy.   Think of flirting as simply having fun with someone and exchanging a bit of positive energy.  You're not trying to woo the emperor of awesome to save humanity from collapsing into a sea of crappiness, you're just having a bit of fun. I know she (or he) is very attractive and they seem to glow with a glittering light on par with the fire of a thousand suns, but they're still only human. 

Be engaging and chatty, but no babbling.   Give them a good reason to want to keep talking to you.  Keep the conversation rolling but know when to stop and turn it around to ask them questions. 

Lose the fear of embarrassment.  No one wants to be rejected and look foolish, but until you're willing to get over the fear of embarrassment you're never going to get anywhere.  I recommend just throwing it all out there, if it doesn't work at least you tried and you can move on with your life.  You can also take comfort in knowing that since they're a stranger you probably won't ever have to see them again.


Thanks to MsJennifer for contributing ideas for this article.


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  • cubana1225 wrote on 07/02/2008
    Nice, very nice, that was helpful.
  • ThePopularSanguine wrote on 07/04/2008
    all that is great but it won't help if you are a fug-mo