The Awkward Flirt Thread

JennyNo1

Literotica Guru
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Inspired by the exchange quoted below in the Litties Vote thread. We've all tried to flirt with someone and had it fall flat, right? Now you can do it on purpose! Give the person above you your best awkward flirt - you can say it, describe it, meme it, or whatever you like. Just keep it fun!

Ladies and gents....ready, set, FLIRT!


Because I only flirt with PLP? Or because I'm the most awkward flirt?

haha, that gif is so cute.

And, I don't know Indie, I have never watched you flirt, but I give fair odds that I could give anyone a run for their money in most awkward flirt. I multiawkward that shit. Not only do I have the wordy awkward going, but I will likely trip over air, knock something over, or spill something on my boobs, while wording awkwardly. Then top it off with a highly awkward random odd fact or offensive joke. I multiawkward flirt at expert level.

I'd like to see this turned into a sport

This should be a category next year!

HA!!!!!

<twirls hairs, bats eyelashes, trips over own feet and falls on her face>
 
Oh, thank you. *Bats my eyes and turns to leave, walking my sexiest walk, not realizing the hem of my skirt is tucked into the waistband of my panties*


With sheepish glances side to side, quickly pulls up your skirt lest another may see.
 
Girl I wanna treat you like my homework. I'll put you on my table and do you all night long. And then fall asleep before it's finished.
 
Let me get that for you gorgeous!
*bends down to get it, slips, knocks you over and ends up grabbing your boob*

I’m classy like that.
 
I think I’ll just watch. I am so clueless I can’t tell when I’m awkward

Well hello. I see you standing there looking all cute, how do I start up a conversation. Oh you are standing by a cooler, I will just nonchalantly go get a drink, that will give me an opening. Grab a can, say Hi, laugh way too hard at things you say, not only the loud everyone looking laugh, but the whole body laugh too. Finally open my drink, just in time to spray us both with soda. My laughing really shook that can. Excellent.
 
Well hello. I see you standing there looking all cute, how do I start up a conversation. Oh you are standing by a cooler, I will just nonchalantly go get a drink, that will give me an opening. Grab a can, say Hi, laugh way too hard at things you say, not only the loud everyone looking laugh, but the whole body laugh too. Finally open my drink, just in time to spray us both with soda. My laughing really shook that can. Excellent.

Seeing you shake your soda and the can explode, walk up, bumping a table on the way. Hey, can I lick that up off you? My stare never leaving your boobs.
 
Seeing you shake your soda and the can explode, walk up, bumping a table on the way. Hey, can I lick that up off you? My stare never leaving your boobs.

Well now not only do I feel awkward because I am, but also because you are at my boobs, so I tell an off color joke about a priest, rabbi, and 3 nuns. Oh yes, it is that bad, so I follow by informing you that a peregrine falcon can reach speeds of 240 miles per hour.
 
This is a near miss flirt that actually happened. When I was freshman at university, I'd eat at Prince Castles hamburger place every Saturday at around 11 a.m. She was always there with two of her female friends. There were no tables and chairs, only student desks and she'd always sit at the desk in the center of a set of 3. After weeks of ogling her and trying to figure out how to break the ice with this beautiful young woman, I decided to get up from my desk, walk over to her and say "hello" and talk with her about nice it was to see her every Saturday. As I started to get out of my desk, for some reason I pushed down too hard on the desktop, where my banana malt, hamburger and fries were placed. I stood up and the food all hit the floor. I spent the next five minutes cleaning up the mess with a towel that the cashier handed to me. I never spoke to the beauty even though we were both in Prince Castles every Saturday until the end of the school year.
 
This is a near miss flirt that actually happened. When I was freshman at university, I'd eat at Prince Castles hamburger place every Saturday at around 11 a.m. She was always there with two of her female friends. There were no tables and chairs, only student desks and she'd always sit at the desk in the center of a set of 3. After weeks of ogling her and trying to figure out how to break the ice with this beautiful young woman, I decided to get up from my desk, walk over to her and say "hello" and talk with her about nice it was to see her every Saturday. As I started to get out of my desk, for some reason I pushed down too hard on the desktop, where my banana malt, hamburger and fries were placed. I stood up and the food all hit the floor. I spent the next five minutes cleaning up the mess with a towel that the cashier handed to me. I never spoke to the beauty even though we were both in Prince Castles every Saturday until the end of the school year.

don't feel bad, every one I share and plan to share on this thread is based on a true example of mine (I said I could win the award if it is a category this year.) That soda one totally happened. I share off color jokes and odd random facts when uncomfortable, and that is just the tip of the iceberg. if this thread keeps going, there will be several things knocked over, a few falls, and some injuries.

surprisingly though, most of my flirt fails are all is well that ends well. Soda guy took it like a champ.
 
don't feel bad, every one I share and plan to share on this thread is based on a true example of mine (I said I could win the award if it is a category this year.) That soda one totally happened. I share off color jokes and odd random facts when uncomfortable, and that is just the tip of the iceberg. if this thread keeps going, there will be several things knocked over, a few falls, and some injuries.

surprisingly though, most of my flirt fails are all is well that ends well. Soda guy took it like a champ.

(Based on a different situation, but still a completely true story)

I see you and walk over with a Pepsi can in my hand. I place it onto the counter near my hip as I lean slightly in a playful attempt to show how relaxed and cool I can be. I suddenly notice my knee is getting cold and feels wet. Looking down, I see that because of the angle I was leaning in, I have tilted my Pepsi can such that the spout is pouring the contents right into my right pants pocket...the fluid falls directly down - missing my thigh altogether - landing straight onto my right kneecap, the wetness expanding in a quickening pace.

I casually lift the can from my pocket hoping you don't notice what I've done. I see you glance down, and despite my hope it's to look at my crotch, you DO notice the wetness on my knee. I glance down as well and try to dream up some sort of clever response.

"Guess I had that one last drip when I used the restroom last..."
 
(Based on a different situation, but still a completely true story)

I see you and walk over with a Pepsi can in my hand. I place it onto the counter near my hip as I lean slightly in a playful attempt to show how relaxed and cool I can be. I suddenly notice my knee is getting cold and feels wet. Looking down, I see that because of the angle I was leaning in, I have tilted my Pepsi can such that the spout is pouring the contents right into my right pants pocket...the fluid falls directly down - missing my thigh altogether - landing straight onto my right kneecap, the wetness expanding in a quickening pace.

I casually lift the can from my pocket hoping you don't notice what I've done. I see you glance down, and despite my hope it's to look at my crotch, you DO notice the wetness on my knee. I glance down as well and try to dream up some sort of clever response.

"Guess I had that one last drip when I used the restroom last..."

well obviously the only thing for me to do here is laugh so hard not only do I start coughing fiercely, but also, soda sprays out my nose.
 
Well hello. I see you standing there looking all cute, how do I start up a conversation. Oh you are standing by a cooler, I will just nonchalantly go get a drink, that will give me an opening. Grab a can, say Hi, laugh way too hard at things you say, not only the loud everyone looking laugh, but the whole body laugh too. Finally open my drink, just in time to spray us both with soda. My laughing really shook that can. Excellent.

With women I’m so shy that scenario would not occur to me. There is someone I seriousMy crushed at a weekly dance. It was only when I needed her help to teach some newbies that I actually talked to her. Much later I figured out she liked me. Since I’m married it’s just a dance flirt thing.
 
well obviously the only thing for me to do here is laugh so hard not only do I start coughing fiercely, but also, soda sprays out my nose.

(The SECOND half of this embarrassingly true story - as happened the very next day)

I see you the next day chatting with someone else and can tell the topic is my "knee splatter" episode from yesterday. I need to show that I can take a joke and am cool about those slightly embarrassing situations, so I saunter over with another full can of Pepsi. I ask the person you are talking to if they would like to see how it happened, so we can all laugh at the silliness. I then proceed to show, in slow motion, what happened.

We all start giggling as I put the Pepsi can down on the counter again, only I place it down too quickly and the can hit too firmly down - causing a lot of foam to spew out the open top. My clumsy, Chevy Chase-like attempt to stop the situation only succeeds on tipping the can over onto it's side - which results in the can spinning quickly like a top with soda flying out in a never-ending stream. I try to stop the rotation, but instead of simply stopping, the can jets off like a bottle rocket and hits the wall across the room.

"See? Neat trick huh!" I stammer - like I meant to do that.
 
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