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First Date Embarrassments: Care to Share Your Story?

There is nothing more embarrassing than an embarrassment on a first date! Sometimes it comes out of anxiety (“wow, I can’t believe she actually agreed to go on a date with me!”); other times they are completely beyond our control.But MOST of the time, just being an out-right “klutz” is the only true explanation.

In fact, “being a klutz” almost turned into a very expensive first date experience for me. Allow me to share my story with you.

This incident takes place during one of the times I came back to Houston while on leave (military term for “vacation”).

What’s the most embarrassing
thing you’ve done or had happen to you on a first date?

Click here to share your story!

My friend had a girlfriend who had a single friend, and since he knew I was going to be in town for a while he and his girl decided that I should meet her single friend for the old “double date” routine.

Since my friend knows the type of females I date he assured me that I would really like his girlfriend’s single friend (let’s call her “V” from now on).

So that Friday when I got into town we all agreed to meet at V’s house and take her car to go and hang out at a few spots around town.

And V was beautiful! I was even more shocked because, since I usually don’t do blind dates, I was expecting the worse.

Anyway, we all switch cars and climb into V’s vehicle. Since I was there for V, I rode up front with her while my friend and his girl rode in the back seat.

Now, I want you to keep two very important contributing factors in mind that will help you to understand where this first date embarrassment story is going:

A) The radio was “off”

B) The windows were “up”

So we’re on the rode trying to figure out where we are going to hang out at. We finally decide to go to the Galleria. Perfect atmosphere (and dining) for a first date.

A) The radio was “off”

B) The windows were “up”

Of course there was traffic out the ass. Typical for a Friday night on 610 South. Everybody’s going to the Galleria to hang out, including us.

A) The radio was “off”

B) The windows were “up”

We slowly make our way through traffic and near our exit. But wait! V needs to move over about three lanes! It’s dark out. All of the millions of headlights are blinding her rear-view mirror vision. How will she be able to tell if she can move over with hitting another car?

I’ve got it! I’ll just stick my head out of the car window to see if the coast is clear!

A) The radio was “off”

B) The windows were “up”


The sound echoed a few seconds more…and then there was silence. Maybe due to the fact that everyone in the car (including me) could not believe that I just tried to stick my head out of a rolled up car window!

No one asked me if I was alright, but I damn sure was checking the window to make sure it was, because even though I didn’t shatter the glass, I hit it hard enough to have cracked it! Now how embarrassing would that have been for a first date with a beautiful female you’ve just met, who now probably wonders if my mom helps my into my pj’s before tucking me into bed.

Well maybe it wasn’t that bad!

And it wasn’t. No cracked car window either. In fact, the “incident” never came up again the whole night.

But that’s not to say it wasn’t on everyone’s mind (including my mind).

What’s The Most Embarrassing Thing You’ve Done or Had Happen to You on a Date?

From realizing you didn’t have your wallet once the check arrived for dinner, accidentally spilling your drink all over your date, to getting your ass kicked, share with us one of the most embarrassing things you’ve done or have had happen to you on a date. Be sure to include any tips you may have on how other bros can save themselves from making the same mistake!

Enter The Title of Your Story (ex. “Me & My Date Outside My Car; Car Keys On The Inside”)

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