The Moment I Knew I'd Never See Her Again

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"I opened the door for her, and then something happened." 

There comes a moment in every relationship, however brief, when you realize 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. This is the third in a series of five we'll be running in the coming days.?

As any right-minded person should be, I’m always skeptical when my mother or one of her friends tries to set me up with someone. The girl in question is inevitably “gorgeous” and “brilliant,” ready for love, but destined not to be my type. I’m just too picky for these sorts of arrangements to work out. Years into my dating life I can count on less than half of one hand the number of times I’ve willingly met a suggested “match.”

One of the few times I’ve given it a shot was about a year ago. Just like a certain population of New Yorkers who migrate to the Hamptons for the holidays, or Bostonians to Cape Cod, my family belongs to a fairly tight-knit community of Montrealers who migrate to Florida for a week or two every winter. In any case, I was in Florida with my family, facing the specter of a planless New Year’s Eve, when my mother’s friend told me that her daughter was going out with some people, including a “gorgeous” and “brilliant” girl that I should most definitely meet. Any plan is better than no plan, especially on New Year’s Eve, when I would have felt guilty doing nothing, so I hastened to the bar to meet up with the group. The “match” turned out to be rather attractive, in fact, and pretty cool, too, so I was glad I went. We had a fun night in a loud bar, exchanged details, and when I got back home to Montreal a week later, I gave her a call and we arranged to meet for dinner.

When I picked her up at her house, she was dolled up and pretty. We had a nice chat on the way to the restaurant, and must have discussed the weather, because I remember driving through a lot of snow that night. She was wearing some awkwardly high heels, which made navigating the space between car and restaurant rather precarious, so my chivalrous instincts were activated. As we approached the restaurant, I opened the door for her, and then something happened: “Thenk yew,” she said, in a nasal, high-pitched, snooty voice that’s typical of girls from the community in which I grew up. The familiarity of it stopped me in my tracks, and although my body carried on into the restaurant, my spirit and enthusiasm were left back at the door. No matter how many nice things I discovered about her that night, I had already learned everything I needed to know at the doorway: that home is sometimes not where the heart is.

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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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That Moment You Know There Won't Be A Second Date

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"Maybe this is the one, I thought. Maybe she’s finally landed in my lap. Were my lonely days about to end?"

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.?

This is the second in a five-part series. Check out the first entry here.

About four years ago, I was sitting at an airport gate in Southern France, after vacationing with one of my closest friends and his new girlfriend. I happened to be single at the time, and traveling with a happy couple really made me wish I had a girlfriend of my own. In fact, I was probably thinking about just that when, lo and behold, as I sat down at the gate, I found myself staring into the eyes of a beautiful girl. She was with her parents, clearly returning from some family trip, had wholesome good looks, a warm smile, big eyes and was wearing leggings that showed off her curves. I was won over almost immediately, and even impressed by how well she seemed to get along with her parents in nice easy conversation. Maybe this is the one, I thought. Maybe she’s finally landed in my lap. Were my lonely days about to end?

She and her parents boarded the plane first, and since they sat ahead of me, I made sure to use the opportunity to cast an extended glance toward her as I walked by. To my surprise, I ended up making eye contact only with her mother, who smiled at me, and was clearly aware of what was going on. In any case, the next time I would see the family was after going through customs, at the baggage carousel. I hadn’t checked my bag, so at this point I was creepily hanging around waiting for an opportunity to make an overture. Needless to say, approaching her right in front of her father was not an option, so I was unsure what to do.

Then came an opening. As they were walking toward the airport exit, she lagged behind her parents ever so slightly, so I ran up and tapped her (lightly) on the shoulder. Nervously, I said, “Sorry to bother you. I just thought you were very pretty.” “Oh,” she said. I asked her “Do you live…?” But before I could finish my sentence she had turned away and rejoined her parents, clearly flustered. I was shocked, dismayed that she denied me, but, hey -- at least I had tried. I walked away toward the trains with at least that bit of comfort.

A few moments later, I felt a tap on the shoulder. “Here’s my email,” she said, and handed me a note. “Oh, thank you” I said. “Do you live around here?” “No, I live down in Dorset on the coast.” (We were in London.) “Oh,” I said. “Long trip!” “Yeah,” she said. “Well, it was very nice to meet you,” I said, and gave her a kiss on the cheek. We left each other smiling, and I was beaming with a sense of accomplishment.

When I got on the train home I of course immediately looked her up on Facebook. It turned out that she was still in high school, and I had been fantasizing about a 17-year-old -- I was 27 at the time. I did send her an email and we had a brief exchange, but the cold hard truth was obvious: this just wasn’t going to happen.

Check out the next entry in this series tomorrow.?

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