Daring to Flirt

you know me, what I’m about to tell you might come as quite a surprise. If you really know me, though, it probably won’t. I’ve never ever openly flirted with someone before; someone I didn’t know. I may have exchanged a smile or a polite hello or carried on chitchat with a cashier once or twice, but my intention is usually just to be friendly. I’ve never been one of those guys who can go up to a complete stranger and strike up a conversation.

The fact of the matter is, when it comes to talking to the opposite sex, I’m extremely shy. I guess I should clarify because most of my friends never see that side of me. But that’s just it. You’re my friends. It’s strangers that I have trouble with. But if you think back very hard to the time you and I first met, you may recall that initially I was quite reserved. I have to warm up to someone and get a feel as to how much Ed they can take, I guess.

I say all that to tell you this: Today I decided I was going to openly flirt for the very first time in my thirty-six years. It all happened while I was out by myself at a Chinese restaurant. It was about 3:00, so the lunch rush was over and the dinner rush hadn’t even started thinking about kicking in. I found myself entirely alone in the restaurant; not another customer in the place.

I was greeted by a cute Chinese girl who was working as hostess/waitress/manager and she had a nice smile and really pretty, dark brown eyes. I made my way to the buffet, filled up a plate, and sat down to eat. After a minute or two, she also went to the buffet, got a plate of food, and made her way to the far corner to eat. She would come over every so often to see if I needed another soda, smile, and then make her way back to her seat.

I observed her while she ate. Not in a creepy stalker way, but because it was either look at her or look at the wall. I noticed she didn’t look up very often. Sometimes she would take a bite of food, swallow it, and then just kind of stare at the tabletop. I wondered what she was thinking about. And then I noticed that I was doing the same thing. I would eat a few bites of food and then find myself zoned out and staring at the empty seat across from me. I wondered if she noticed me and if she wondered what I was thinking about. Or if, in the silence of the restaurant, I just kind of melted into the background.

It was during this time I decided I would try to flirt with a stranger for the very first time. I’d never done it before, so I didn’t even know if it was a power I had. I’ve never ever talked to a girl I thought was cute just up and out of the blue but I figured this would be as good a time as any. I was under no misconception that I would say or do something that would make her swoon and we would end up driving off into the sunset…I just wanted to see if I could. Other guys can do it, why can’t I? Why haven’t I?

But it had to be real; I wanted it to be genuine. I didn’t want to just throw a line out there like an overeager fisherman. And I also didn’t want to come off as the sleazy jerk hitting on the waitress. After all, the food there is really good and I didn’t want to become “that guy.”

I started to talk myself into it. Would I actually be able to go through with it? Or would it just be like every other time where I tell myself I’m going to do it and then, in the moment of truth, I chicken out? I opened my fortune cookie and it read, “Your present plans will be successful.”


I stood up and put on my jacket. She noticed me and made her way to the cash register. and I got really nervous. Doing stand-up in front of 350 strangers is cake compared to this.

And this is how it went:

Her: Was everything OK?
Me: Everything was really good.
Her: (smiles) Good.
Me: Do you mind if I ask your name?
Her: Jenny.
Me: Jenny?
Her: Yes.
Me: Jenny, you have really pretty eyes. (I didn’t tell her this in a Barry White/Ladies Man-type way, but just stated it friendly and matter-of-factly like I was telling her it was a nice day outside)

Jenny looked down and didn’t say anything. And then I decided I’m an ass.

Jenny counted out my change and I was filled with self-loathing. I thought everything I said came out sounding genuine (she really did have pretty eyes) and not-at-all cheesy but what do I know. I’m a big dumb guy.

She handed me my change and I thanked her. She still didn’t say anything. I smiled and turned to walk out the door. As I pushed it open I heard her say “Thank you.” I smiled at her, nodded, and continued out and then she said it again.

“Thank you.”

Two thank yous. I guess it could have gone worse.


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