The Nightmare Before Valentine’s Day

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Valentine’s Day, February 14th comes and goes every year, and every year there’s men and women arguing the significance of the so-called holiday. Of course, Valentine’s Day will mean different things for different people. For singles, it’s a harsh reminder that they’re still single e.g. Singles Awareness Day. And for couples (specifically men), it’s a reminder to make their significant other feel special.

I’ve lived through twenty-seven Valentine’s Days, and there is one Valentine’s Day that serves as a reminder of just how harsh the holiday can feel.

Let’s rewind to almost ten years ago.

The Nightmare Before Valentine’s Day

In 2003, I was a single, hopelessly romantic yet sexually frustrated college freshman with an innocent crush. Her name was Karen, and I had first met her during college orientation. Like any crush, I was infatuated with a girl that caused a flurry of butterflies to fill my stomach whenever I thought about her.

Throughout the school year I was hoping my friendship with Karen would blossom into a romantic affair. That I could be more than just a friend to her; possibly her boyfriend, and who knew, maybe this was the girl I was going to call my wife, the mother of my 2.5 children, and live within a house featuring white-picket fence.

Karen and I seemingly had so much in common. We would talk for hours about anything and everything. I would day-dream about her smiling at me, go to sleep dreaming about her lying beside me, and anticipated doing it all over again the next day.

For several months, I never told Karen how I felt about her. I wanted to romantically pursue her, but I didn’t exactly know how to transition from friends to lovers.  Also, I didn’t want to risk making things awkward for her and possibly ruining our friendship. I was hoping that fate would in one way or another intervene to bring us together, just like a romantic comedy.

When Valentine’s Day came approaching, I figured that day would be a great opportunity (read: excuse) to finally display my interest to her. I was somehow convinced that Karen would most definitely be my Valentine and that this was all fate (because that’s all I knew). Wanting desperately to impress her, I reserved a floral arrangement, booked a table for us at a fancy restaurant, and purchased tickets to a Broadway show I thought she’d enjoy. I was driven to make Valentine’s Day a special night for her.

A week before Valentine’s Day I assembled the courage to ask Karen out… over text. Minutes of no response felt like agonizing eternity while I waited anxiously near my phone. My palms were sweating, my heart racing; I had to force myself to remember to breathe.

A half hour went by and nothing.

An hour later and there was still no response.

After an hour and a half, Karen sent a text that she would call me later in the night.

I was very confused. It wasn’t exactly a “no”, so there was the hope she’d be my Valentine?

More anxiousness waiting by the phone, and when Karen called a couple of hours after her text, she mentioned how she was “sorry”. She didn’t “feel that way about me” and she “wasn’t looking for a relationship”.

Her words triggered an emotional pain that felt like a punch to the gut. I remember trying to fight back tears, still in shock that my “friend” whom I cherished just rejected an offer to be my Valentine.  Logically, I didn’t understand it at the time.

friendzone johnny

being a “nice guy” loser

My blissful vision of fate bringing Karen and I together turned over to a friend-zone nightmare that shattered my confidence. Angered, hurt, depressed, it would be four years until I ever asked out another girl. Four years!

The nightmare then was being a kid with a broken-heart. In retrospect, the nightmare was living in hope.

I hoped Karen would fall in love with me, but no girl is going to falling love with a spineless coward.

I hoped Karen would understand me, but expecting a girl to be rational, sincere, and logical is naive.

I hoped Karen would feel the same way about me, but emotions can’t be forced.

I hoped Karen would appreciate my efforts, but she had no obligation to do anything.

I hoped Karen would respect me, but I didn’t even respect myself.

I understand why Karen refused to be my Valentine. Instead of a mediocre experience of unrequited love, I foolishly allowed what happened to chisel my fate, when I should have been making my own. This would’ve meant approaching girls as a man to woman, not a friend to woman; meaning better to move fast with girls than to be indecisive and take things slow.

As I type this post, I’ve had close to a dozen different girls recently contact me. These were girls I previously dated, hooked-up with, or came across, who all of a sudden wanted to get together. With Valentine’s Day approaching, this may or may not have something to do with it. Let’s hope I’m not these girls’ Valentine’s Day nightmare ;)

And for the singles without someone special to share Valentine’s Day with, remember this-

Cherishing someone who doesn’t cherish you back is taking time away from those that would jump at the opportunity.  Recognize that there are some people you will be more compatible with than others; but you can’t just hope they appear.  You need to put yourself out there and be excited to meet new people if you ever plan on meeting someone special.  It takes time, just realize your past doesn’t have to be your destiny.

JT Styles (43 Posts)

JT Styles is a dating coach located in New York City. He has trained extensively in the social and seductions arts since 2008 and teaches a distinctive style of approaching women based on masculinity, honest sexual expression, and understanding female emotion. His clients include professional executives, college students, divorced singles, the sexually inexperienced, and any man that wishes to improve his current dating situation.

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  1. danny says:

    Cool story

  2. greenlander says:

    lol, that sounds a lot like my early history with girls too! I’m not laughing at you, I’m laughing at myself because I once felt the same pain…

    • JT Styles says:

      I’m sure every man on this planet has dealt with unrequited “love”. It happens, and better to move on than to let that hurt affect your mojo.

  3. Vince says:

    This is really helpful for my 1itis problem. Is she still your friend now?

    • JT Styles says:

      She’s a Facebook friend, haha.

      She got married last year, but just got divorced. I have no interest in pursuing her now.

  4. plat says:

    My GOD! Some of my under-confident male friends need to read this site and take notes. You were in your college days when this happened to you, I know guys who are breaching 40 and going through the same thing.

    The problem is confidence and dreaming too much. The thing I always tell them is to take that first step sooner rather than later, find out if you actually like being around her, then dream of what you can do–together.

  5. R1 says:

    I had something similar happenings to me when I was in high school.. I was depressed for the better part of a year because she just stopped talking to me for a month when I asked her out.

    I think that this was probably the defining moment in my life that led me to learn pick up, four years later…


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