I've never been in a relationship with a woman. I've been told I'm too clingy

'I find socialising difficult to the point of being distressing.' Photograph: Forest Woodward/Getty Images/Vetta

I'm a student in my early 20s and have never been in a romantic relationship with a woman. I've been told by those who have been the targets of my affection that I'm too clingy. I don't know how to overcome this. I find socialising difficult to the point of being distressing, and have no hobbies that bring me into contact with others. So whenever I become close to somebody, I feel I have to let her know I'm interested. This has the opposite effect to that intended, and pushes those I'm interested in away from me. The more this happens, the more depressed and withdrawn I become – and the more desperate I feel.

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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.

Check our When Things Fall Apart Part 1 and Part 2.?

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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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You'll Never Guess What Month It Is...

You'll Never Guess What Month It Is... Getty Images

Ah, the month of May. The weather heats up, the clothes come off and society encourages everyone to masturbate themselves silly. You read that right -- May is National Masturbation Month. So take a guilt-free break from trying to win over the girl of your dreams and focus on yourself for a little instead with the knowledge that everyone’s cool with it.

And if you’re brave enough to help destroy the stigma around self-love, you can raise money for sex-awareness groups at events like Philadelphia’s Masturbate-a-thon Fundraiser. Only 29 days left in May. Better get started!

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