99 Problems

This long-haired stranger grabs my hand and walks me to a dark, unlit corner. We place our drinks on a ledge by the window. I position my hand gently on the small of her back and lean closer. The smell of cocoa butter and peaches emanates from her skin. Just as I'm about to kiss her, she pulls away and curiously asks, “Do you know that girl?”

Which girl?” I respond hesitantly, fully aware that this question always leads to nothing but trouble.

The one with the side of her head shaved, staring me down, holding that other girl's hand. She looks pissed.”

9 Weeks Earlier:
We were having a really good time. We met about an hour ago to the sound of one of those club rap songs with no specific agenda or message other than to make you enjoy life, feel good and dance. Our conversation, like the song, wasn't particularly filled with substance or intention. We didn't have any sort of serendipitous connection nor did we discuss ideas or beliefs. We merely laughed and talked. She was just another pretty girl out for drinks, enjoying her Thursday night. She was precisely what I needed. The last few weeks had been a roller-coaster of tough times with work, family and life in general. She – combined with drinks, laughs and good friends – was the only medication that overcame my Tylenol tolerance. I had laid out some significant ground work and a good night was slowly manifesting into a great one. Just as I was about to ask her if she wanted to leave and maybe continue the night elsewhere, she turned to me and said: “I really like you. You make me feel good, but I think there's something you should know about me. See the girl I came with? She's not exactly just my friend. I'm not into dudes in that way. Or in any way, really. But we can still hang out as friends?”

I'm momentarily confused. It takes me a second, but I have an idea who this tropical fruit-scented stranger could be referring to. I turn around and, nearly unsurprised, I see exactly who I expect to see. The choices really get narrowed down with a statement of that nature. There aren't going to be too many lesbians in this city with reasons to fixedly lay death stares at me through their clear lens black Ray Ban Wayfarers at 1 in the a.m. She has no justifiable reason to do so either, but there she is, standing by the bar in her black leggings and blue Ralph Lauren men's Polo shirt with the right side of her head shaved, holding her girlfriend's hand, burning a hole right through my back and into the cocoa butter girl's brown eyes. She does not look impressed. We eventually catch each others’ eyes and she pseudo smiles at me while dropping her girlfriend's hand to wave. I have to make a choice, continue my night with miss cocoa butter, or stop it in its tracks, grab my drink from the ledge and walk over to her. Leave it to me to make the obvious wrong choice.

6 Weeks Earlier:
I almost had a “Chasing Amy” moment with her. It had been a build up of emotion and confusion over the last couple of weeks of hanging out and hooking up. The two of us were in her apartment, sitting on her black leather couch, drinking a bottle of Pinot. She had just finished making us a completely vegan dinner and began to recount her adventures from her latest trip to her hometown: New York City. She amiably informed me that while she was there she had picked me up a small keepsake. She grabbed my hand, opened my palm and placed a model-sized Statue of Liberty refrigerator magnet in it, disarmingly saying, “Now you have one too”.

During my past late night visits and after sex trips to her fridge, I would frequently comment on her sentimental fridge magnet that held up a picture of her father. This charming gesture virtually cued me to go all Tom Cruise Mission Impossible on her and tell her I wanted more than just the sex she constantly – candidly, even – reminded me that this was.

I accepted her New York City keepsake and was about to say, “Hey I think I need to tell you something,” but before I could even begin to mutter a word, she leaned in and kissed me. We moved the activities to her bedroom. As soon as she was done, she turned to me and said, “You know that I'm completely gay right? I'm totally not bi. We're having a good time, that's all this is.”

That statement quickly put an end to any thoughts of romantic pursuit. It also killed my manhood.

With a slight hesitation but no real second thought, I leave the comfort of clarity and walk head-on into the heart of lesbian-chic complexity.

I innocently ask her, “Hey stranger, what are you doing here?”

To which she nonchalantly responds, “Just out for some drinks with my girl. Can I talk to you for a second?”

She whispers something in her girlfriend's ear and motions me outside.

3 Weeks Earlier:
I've had it. It's my fault. It's like I never want to learn my lesson. We'd been hooking up on a nearly nightly basis over the last few weeks and after every time we do I would get the same prepared speech. She’s a lesbian, not bi. She has no feelings for me. It’s just sex. This made absolutely no sense to me... How can a lesbian want to have sex with a guy? This ironic, seemingly paradoxical situation I now found myself in eventually tempted me to ask that very question to which she angrily responded, “I'm gay. Don't you get it? I don't like guys!”

In an attempt to illustrate the obvious flaws of our situation, I asked, “Um, then why are we having sex? Call me crazy, but it seems to me that you actually do like guys. I know I don't completely understand the intricacies of being gay, nor do I pretend that I do, but isn't the fundamental definition of ‘being a lesbian’ that you don’t want dick?”

That statement fuelled her anger. She rolled her eyes at me as if there was a universal homosexual language that I – as a straight guy – could never understand. She began to speak to me condescendingly – like you would to an infant. I’m guessing she thought this sudden change of tone would prompt a critical realization that I had missed in the past several weeks. It didn't.

Look Lorenzo. I like you, I really do. We connect and I definitely like having sex with you. I even think about you when I'm with girls, but I'm a lesbian. I don't like guys that way. You just don't get it and you just can't seem to accept that. I think that you can’t handle what we have, so we should just be friends.”

Huh? After the most confusing clarification in human history, I decided that there was no point. I was done with sadistically coming back for more.

We're standing outside and the snow is coming down hard. I could barely see anything around us. I left my jacket inside so I'm freezing. She takes a step closer to me. I can see her breath through the flakes of snow. She wraps her arms around me, kisses my neck and quietly says, “I've missed you. Let's go back to my place.”

For a moment I lose myself, but I quickly regain my focus and gently take a step back, away from her. Half confused I ask, “What are you doing? You made it perfectly clear to me that you're a lesbian, not bi. And because of your sexual preference, there is no way you and I should ever catch feelings for one another. ”

She looks down, lost in a moment of thought. She eventually looks up and calmly says to me, “Tonight maybe we can pretend I'm not. And in the morning we can talk about all this. Lorenzo, you know me better than anyone.”

She was finally ready to talk, but I had completely lost interest. A few weeks ago, I would have given anything to hear her say any semblance of this combination of sentences and words. Now, looking at her, the situation was no longer appealing. The snow might have made it harder to see anything around us, but it certainly cleared the visibility on the path ahead. Things were finally clear. I didn't know her. She barely knew herself. I had never met someone who was so unhappy with who they were that they tried this hard to pretend to be someone else. Shaved heads and manly shirts do not make a lesbian. I once knew a girl very much like her. I fell for her and she broke my heart. I won't make that mistake twice. Not now. Not here. Not ever. Just like this pseudo-lesbian, she was always addicted to the crash. For people like them, the heartbreak is never enough.

I wipe her bangs from her face. She anxiously looks at me. I ask her, “Remember the song that was playing when we first met?”

She thinks for a moment, “Ya, 99 problems by Jay. I told you that's one of my all-time favourite tracks. How could I forget?”

I misleadingly pull her closer and recite a seemingly prepared speech of my own.

Well Jess, I don't have a lot of these alcohol-induced moments of clarity. I'm not a person that makes a lot of right choices. I'm sure I have more than several idiotic moments and choices left in me, but tonight I'm determined to make the right one. In life, I’ve always believed that I had to go through a lot of the wrong ones to meet the right one. Don't take this the wrong way – although there is no other way to take it – but you my ‘friend’ are most definitely one of the many wrong ones I’ve made. Unlike your favourite song, I have ninety nine girl problems, but a lesbian ain't about to be one. I'll see you next lifetime. Don't call me.”

She's going to make someone very unhappy one day, and tonight I made sure it was never going to be me. I turn my back to her, walk out of the snow and head back to the simplicity of Caribbean scents and heterosexuality.


  1. Posted on February 11, 2011
    great work…. more more more

    Posted on February 11, 2011
    Your insight always amazes me. I love the way you express your opinions and your honesty is refreshing

    Posted on February 11, 2011
    Great work! keep em coming

    Posted on February 11, 2011
    Your passion and self awareness make this piece what it is. Good job

  2. Awesome. Can’t wait for the next one.

  3. 99 problems...and a girl is all of them. lol

  4. Cool story! I like it :)