True Story: I Left Him Stranded at Homecoming and THIS Happened | Dating Story Chapter Two — Jeremy

True Story: I Left Him Stranded at Homecoming and THIS Happened | www.pinkcaboodle.comHave I told you about that time I ditched a date?

That’s a rhetorical question — I know I haven’t.

As I strive for new dating opportunities in 2019, I can’t help but think of all the experiences I’ve had so far.

In Chapter One, I mentioned that I’m starting to realize how my own insecurities may have contributed to my singleness.

This was a real eye-opener for me, and ever since then, I’ve been thinking of all the moment’s I know I let my fears get the best of me.

Like that time I left a date hanging at the door of my college homecoming dance.

Yeah…that happened. And it wasn’t because I didn’t like him — I actually liked him a lot. It was purely because I chickened out.

Crazy right? Here’s what happened…

It was my senior year of college. All four years of school, I worked on campus as part of the campus events/receptionist team.

Besides being with my friends, working in the events office is one of the highlights of my college education.

I met so many people and attended so many concerts/events, my time as a box office attendant made college extra special.

All this to say, working in the office, we always had the heads up on upcoming school dances.

One afternoon, my co-worker and I were talking about the homecoming dance, and she asked me if I had plans on going with anyone.

Of course, my answer was no. Somehow, the conversation shifted to who I would like to go with.

This was the start of it all….

For the sake of privacy, we’ll call him Jeremy.

Jeremy was the hottest guy in school. At least in my mind, but I’m sure the majority of the girls would agree with me.

He was captain of the basketball team. Very tall, again, very handsome. Most importantly, you could tell that he had a kind heart.

I mentioned this to my co-worker, and of course she loved it, and encouraged me to ask him to the dance.

To backtrack a little bit, college was very hard for me confidence-wise. On top of just being insecure, I wasn’t surrounded by a lot of people who looked like me, and I felt like I couldn’t compete against the girls who I perceived to be skinnier, ‘blonder’, and prettier than me.

With this in mind, I rolled my eyes and laughed off the idea of me asking Jermey to the school dance.

Fast forward a week later, its the day of the homecoming dance, and my coworker comes up to me with a smirk on her face.

Right away I knew something was up. And I was right.

Turns out, she emailed Jeremy letting him know that I thought he was cute and to meet me at the homecoming dance at 7pm.

And to make it worse, my entire office new about it!

I couldn’t be mad, I knew it was all out of love and support.

Everyone was very encouraging of me, but I was terrified out of my mind.

What would I wear? Will he laugh at me? Would he even show up? Those are just a few of the thoughts running through my head.

I was terrified. So, instead of picking out a nice outfit and getting ready, I did the only thing I knew how to do…I worked…the homecoming dance.

I was responsible for scanning everyone’s ticket. Doing this only made things worst — not only was I nervous wondering if Jeremy was going to show up, I had no way to avoid him in case he did.

7pm came and passed, and there was still no sign of Jeremy. And I was so relieved that I didn’t have to confront him about the email that my coworker sent.

But then…….the clock struck 8pm, and there he was.

I know how ridiculous this story is now, but in the moment, it was terrifying!

And unbelievably awkward.

I didn’t know what to say, so I just kinda stood there and stared at him (lol!).

*I’m cringing just writing this*

After a few awkward moments, Jeremy smiled down at me and said that he was going into the dance, and that he would wait for me to join him.

Everything in me wanted to muster the courage to go in there. But I didn’t.

I chickened out. I continued scanning the last few homecoming tickets, then I left back to my dorm room to hide under my covers in shame.

This is a life moment that I wish I could go back and do over.

But not for the reasons you think…

Of course, I would have loved to dance the night away. Who knows what might have happened next.

But what I wish most is that I didn’t let my fears get the best of me. I automatically shut down the possibility that Jeremy was interested in me. And again, I thought the fact that he show up was at the expense of a joke between him and his friends.

I wish that I wasn’t so critical of myself to think these things to begin with.

This is where my learning lesson comes in.

I can’t deprive myself of opportunities because I’m scared, or afraid of what people might think of me. Whether it be a date, a job interview, or anything new and scary.

Again, it’s okay to be nervous of the outcome. But never sell yourself short of the opportunity, whatever it may be.

I don’t ever want to be left wondering what if. I think this is partly why I forced myself to message “store boy“.

With that being said, don’t be afraid to go out and dance. As hard as it may be, don’t do like I did and run away from your fears.

Life is too short to be weighed down by your own insecurities.

While this is one moment that I will never get back, it is something that I can learn from — dating-wise and just in life in general.

So yes…I left a guy stranded at the homecoming dance. But I can tell you one thing…it won’t happen again *wink wink*

Until Next Time,

Maya <3


Maya is owner of Pink Caboodle, specializing in Fashion and Body Positivity.

  1. I love this story! Thank you for being so honest! I realized how my own fears held me back in my career. I can relate! But I wonder where this young man is now…. 🙂

    1. Abbigail!! Thanks so much for stopping by!!its crazy how much we can let our fears dictate the decisions we make…or don’t make for that matter. But here’s to breaking loose in 2019. Oh, and I know exactly where this young man is 😉 that ship has sailed though…right?

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