The Moment I Knew We Were Never Going To Be Together

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"I emerged from down below and whispered six words in her ear -- words not carefully chosen, but ones that in the moment I thought might compensate for my oral ineptitude." 

There comes a moment in every relationship, however brief, when one of you realizes that things are destined for failure. Sometimes it’s something you do, sometimes it’s something she does and often it’s nobody’s fault. Either way, these moments remain with us, seared into our memories, as testaments to our deeply personal journeys through romantic life. This is one man’s attempt to share some deeply personal moments of his own. Here's the first in a series of five we'll be running for the next five days.

I was a late bloomer. At 17, I had never had sex, had recently broken up with my first "real" girlfriend and somehow managed to get a beautiful, popular and sexually experienced 19-year-old girl named Allison to go on a date with me. Needless to say, I was nervous and unprepared. I was also a bad conversationalist at that point in my life, so dates had the potential to be excruciatingly awkward (I like to think that this is no longer the case). Despite all this, I somehow did well enough to earn a second date with Allison: a movie night in her parents' living room.

So there we were, in her living room. Her large, intimidating Rottweiler panted close beside us at the foot of the couch and, unable to focus on the movie, we began to make out and were on top of one another. We kept kissing until our lips grew numb and it became painfully obvious that we needed to start doing something else. Nervously, I began to descend toward her vagina to do what any “experienced” lover would do. I had never done this before. And as I attempted to make heads and tails of what was going on down there (I didn’t), I was very aware that my obvious lack of expertise was revealing me for what I truly was: a sexual novice.

Anxious about exposing my inadequacies further, I emerged from down below and whispered six words in her ear -- words not carefully chosen, but ones that in the moment I thought might compensate for my oral ineptitude, and triumphantly announce my manly competence and desire to take things to the next level. “I’d love to be f*cking you,” I said, in a strained, awkward, growling whisper. She didn’t respond, and this threw me into a state of total anxiety. While continuing to kiss her, I kept playing the words over in my head, wondering if I had screwed things up, insulted her, given myself away even more or god knows what.

Which ever way you cut it, those words ruptured something in the relationship, as I saw it. They were just too ambitious for me to utter with any hint of authority, and the resulting awkwardness was too intense to bear. We never saw each other again.

Don't miss Part 2 of this five-part series tomorrow.?

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