Throwback: My First Time (Girl Fail #20)

G FAILIt would be illogical to write – not to mention relive – my Girl Fails without telling you how it all started. I’m going back to high school for this story; back before I had a modus operandi, back before texting and when everyone was on AIM, back when I was battling unwarranted boners and jacking off every 15 minutes, and back when I was oblivious to anything sexually tacit (oh, the irony). Despite my mercurial nature, there was a sensational brunette in my 9th grade English class sitting beside me and I was smitten.

She was shy, allusively charming and, although the same age, blasé – as if she had been on more adventures than Amelia Earhart. But, I could make her laugh. The more I did, the more confidence I acquired and even I was surprised by this recycling of energy. Her best friend sat in front of us and pretty soon we all became close. After flirting for 2 months, I asked her out. She said yes and I got her email address and screen name (not many kids had cell phones at this point). I was ecstatic and eager to fill my friends in on my success, which is why I was surprised to find a rejection note in my locker the next day. She said her life was complicated, she liked a man in another state, and that I was a good guy. It was my first real rejection but I didn’t let it stop me from trying again.

FriendClass was awkward for a week but we got back into our old flirtatious habits and it was business as usual till the end of the year. We chatted online all the time and sent each other funny photos via email. End of the year finals were here and with Summer break quickly approaching, I was afraid I’d be immured in the friend zone for eternity unless I asked her for her number. I couldn’t bare the thought of not seeing her for an entire season.

My plan was to ask her after our English final. Well, guess who finished the test in half the time I did and was picked up by her parents? I was abject. Alas, all hope was lost!

Not quite. Her best friend was waiting for the buses like I was. Believing it was my only shot, I asked her if she’d give me our mutual friend’s number. Noting my candor, she smiled and gave it to me.

“She likes you, you know,” she said, surreptitiously glancing over her shoulder as if her friend would suddenly appear.

I called her that evening, explained how I got her number, how I was sorry I didn’t ask her personally but with the summer here and I didn’t want to lose touch. After speaking for 5 minutes, she said she had to go and I suggested that we hang out sometime.

She sent me an email that night strongly voicing the err of my ways. What I believed to be an innocuous phone call between friends turned out to be the most menacing, disgraceful act normally executed by heartless tyrants. She went on to say that we had absolutely nothing in common, I had no idea who she is or where she’d been, and I was thoughtless (there we go with the irony again). She closed by threatening violence (she had strong, “protective male friends”) if I ever dared to call her again.

ThinkFrom that moment on, I began to over-think every single statement, action, or pass I made at the opposite sex. I feared that no matter how close I got to anyone, I could still be regarded as an evil threat. Every pact could be broken at any time. Every gallant gesture could be misinterpreted as malicious. Every compliment could be tainted by selfish and hidden intentions. As much as I challenged these thoughts, my subconscious seemed to open the door and graciously invite them inside to percolate.

After two years of silence, she instant messaged me randomly one day. (Interestingly enough, I was dating someone at the time.) She asked if I hated her. To be honest, I struggled to find the relevancy of her question since we remained strangers for the past few years. Then again, it was high school and we were all dramatic and peevish twerps expecting our world to end by means of a merciless calamity. Most of us aren’t like that anymore. Anyway, I replied saying that I didn’t hate her and asked if everything was okay. As if she was in a confessional, she wistfully explained what was bothering her and confided in me. She felt lonely all the time and pushed others away for no reason. She regretted the email she sent me and wished she could have taken it all back. Although it was a strange time for an apology, it was nice to hear it from her.

Regardless, the damage was done. She changed the way I pursued women all throughout college and, most likely, is the reason why I continue to contemplate my presence around women to such an unnecessary degree.

Now would you look at that? That’s some Class A psychologist babble right there, and it was all for the price of one large coffee at this quaint cafe on the corner. What a steal!

-Single Guy in NYC
@SingleGuyInNYC

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3 thoughts on “Throwback: My First Time (Girl Fail #20)

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