Walking The Walk

I used to go to this coffee shop that made sub-par chai latte’s and totally overcharged for a plain large coffee.  Even though I worked at a job where I constantly preached the importance of money management (including giving up your daily $3 latte which, by the by, will save you over $750 a year!) I still went to that coffee shop religiously each morning on my way to work.

It was for the boy who worked in the coffee shop.

I’m naturally a flirt.  I don’t even realize when I’m flirting cause I fall into the habit so quickly.  And I had so much fun going in and for 10 minutes flirting my little heart out with Barista Boy.  The best part about it was that there was no strings attached, there were no expectations of what was going to come with the flirting.  It was just healthy, daily morning flirting.  Kinda like going for a run but without the sweat and messed up hair.

There were no strings attached because I am so darn shy there is no way I was ever asking him out.  And for some reason, boys don’t really ask me out either.

Shy girl
Photo Credit: Getty Images – Thomas Northcut

Fast forward to this past weekend hanging out with a couple gals at the Portland Pirates game.  Standing around waiting to meet up with some other people, a very cute boy started talking to me.  Dark hair, much taller than me (not that it takes a lot,) super nice and smiled a lot.  He was one of the folks we had to meet up with, so it totally made sense.

I could hear my voice getting very giggly and I knew I was tucking my hair behind my ear like I was a method actor.  I mean, this boy was quite adorable.

He left to get something and one of the women I was with tugged at my arm exclaiming “He’s cute and he’s flirting with you.  You should go for it!”

I continued with the flirting.  I even asked Twitter’s opinion of whether I should be so forward as to ask out this guy I barely know.  Resoundingly the best response was to just do it – like ripping off a band-aid, anticipation is the hardest part.

But I couldn’t bring myself to do it.  To put myself out there.  I’m not even sure what the problem was.  I worked for years in sales, rejection is like old hat to me.  It’s the awkwardness, the trying to be cool enough for someone to want to go on a date with.  Figuring out if your flirting is actual flirting or just human interaction flirting. Wondering if he feels it back or if you are just being totally silly.

Sure I can talk a mean flirty talk, but to date I’ve only been able to walk that “asking out/more serious than an eye-bat” walk a handful of times.

How about you?  Have you had those situations where you really wanted to ask someone out, but couldn’t muster the awesomeness to do it?

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