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Shoulda, Coulda, Woulda Moments

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ZainTheInsane

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Okay...have you ever had a moment where you should have done something...could have done something, and later regretted it because anyone else in the same situation would have done what you were thinking of doing?

That's what I'm talking about when I refer to a shoulda, coulda, woulda moment.

And Friday night, I had a BIG one of those...
I was out with the WCMF crew, bar hopping, donig advertising and promotions for a specific type of beer, and we were at our last bar. I come in, sit down, and relax. Suddenly the bartender asks, "What would you like?" I look up, and BAM! I'm staring into the eyes of an amazingly beautiful, natural red-head, her eyes a beautiful gray, and she was curvy, lovely voice, and just DAMN!

Of course, because I was working, I had to decline. About five minutes later I think of an idea...silly as it is...I say to myself...it is the end of a shift, Moe won't mind if I have one drink. So I make this plan, to ask very casually for my drink, and her number...doing so in a way in which, I'm hoping, will be either amusing, or charming. So, just as she comes back over, I begin to get my courage up...and then...the song "Before He Cheats" by Carrie Underwood comes on the jute-box in the corner...and a few of the girls at the bar as Erica (the bartender) to start singing it. So she does...and she's magnificent...I was blown away!!

She sung the song better than Carrie Underwood herself! It was amazing...so yeah, this sorta deflated my bubble for a moment...then I tried to find something to look at while not bumbling...and I spot a newpaper article on the wall. I read it for a bit, then focus on the picture in the article...

THE BARTENDER WAS IN THE PICTURE!


Turns out, she was Erica Brown, a girl who I'd heard about a while ago in the Democrat & Chronicle (local news), and suddenly all my aspirations for asking this girl for her number went to zero. I thought to myself, she was completely out of my league...this girl is an amazing singer, and is beautiful, and just wow...Plus she apparently was going to the University of Rochester for something...I don't remember what, but i remember that the UoR is one of the hardest schools to get into...

So, yeah...silly me...I sorta turtle-shell for the rest of the time, and never end up buying my drink, or asking for her number.

Later while talking to my best friend, he said something which made this a serious Woulda, Coulda, Shoulda Moment. He told me, "No girl is out of your league unless she says she is." And at that moment in time, I realized how stupid I'd been. I could have at least ASKED. I might have gotten embarrassed, or laughed at, or any number of things...I could have even gotten her number...

But, I didn't. And though it won't be something I regret for the rest of my life or anything...it is definitely one of those moments I'll remember for a little while afterwards.

So, that's my most recent Shoulda, Coulda, Woulda Moment...do you have any? What've your worst ones been? What ones have you been able to go back and do?
 

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