Who has two thumbs and sucks at flirting? This girl!

You may think I'm kidding, but I'm not. I suck at flirting. Let's take Saturday night as another shining example of this point.

Scene: Unnamed Lakeview bar and grill, me entering to pick up a carry-out order. Dressed in an Old Navy tank top (with a small smoothie stain I discovered later), bra strap exposed, looking very warm and flustered from the heat and wearing a cotton skirt with little make up on. I go up to the bar to pick up my order and two nice-looking guys are sitting at the bar as well. Non-spoken descriptions are below in italics.

Guy 1 (the blonde-haired guy): Looks at me, gives me a warm smile, which I return. Hi there.

Me: Hi

Guy 2 (the dark-haired guy): Also looks at me and smiles while Guy 1 continues to throw looks my way. Hey there.

Me: Hi

Bartender: Okay here's your order. He tells me the amount and I hand over my credit card, Guy 1 and 2 are still smiling at me, which I continue to smile back.

Me: Thanks, turns to Guy 1 and 2, have a good night giving them my patented "look"

Guy 1: You too, I leave but can feel someone watching me as I go. Tempted to turn around and give one final look and smile but do not.

End scene

Okay so that might not have exactly been me flirting and of course there is the likely possibility the guys were just being polite and watched me walk away out of horror for my outfit choice. Either way, the entire way home I'm kicking myself in the a** for not saying more to them or really anything. These guys were cute! But as I walk home, cursing, I realize I can't go back because they've seen me with a carry-out order so if I go back I'll be a) psycho for going back to ask about some asinine thing with my food or b) obvious that I would like them to ask me to stay for a drink or offer to join them. What is my problem?

And yet again I have solidified the fact that I suck at flirting, mostly because I still have a hard time believing a guy would want to flirt with me. I really not trying to be self-deprecating here but I'm totally serious! I am awful when it comes to guys because I have no idea what to say to them or my snippy, sarcastic humor ends up scaring them away or putting me in the "friend" category almost immediately. I'm the buddy, the wing(wo)man. Guys talk to me to get to one of my friends. It's so true.

Here's another solid example of my poor flirting skills. Right after college, I was living in Wisconsin and could not find a decent job to save my life. So one night, I go out with my friend for her birthday and I end up hammered and making out with her boyfriend's friend at her apartment. While this guy and I are fooling around, he whispers to me, "what do you want?" And I sh*t you not, this is my drunken answer, "a job." Really, I'll let that sink in for a moment because that is what I said without even thinking. And his response? "I can't give that to you." And thus the fooling around was done not long after that comment.

This guy would have done anything I asked him to with his mouth or hands or both, resulting in my toes curling and likely being rendered speechless and my answer to him is, "a job." In actuality, I wanted him to do something with his hands or mouth to take my mind off not having a job, but apparently I could not communicate in the heat of the moment. My friend could not stop laughing when I told her that. It was embarrassing. 

Once after a night out in Chicago, I had a guy offer to take the bus home with me, even though the El would drop him off closer to his house, and my comment to him was, "why would you do that?" My friend Sarah, who was trying to set me up with this guy (who is now engaged to someone else), looked at me like, "Jess do you seriously not see why he would do that?" And my answer was yes.

So next weekend when we're out, my goal is to turn off the inner monologue long enough to give flirting a real try without sounding like a moron. And I'm actively recruiting for my own wing(wo)man so let me know if you're interested in applying. References are appreciated.