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Writer's pictureJenn Roberts

Every Cyclist is Clearly in Love with Me

Updated: Feb 5, 2020


Some women have the remarkable ability to instantly recognize when someone is hitting on them. I am not one of these women. Unless someone pulls a Love Actually moment on me and reads cards that say “I am very interested in you! Let’s date!”outside my door, I cannot tell for the life of me whether or not someone is interested in me. But one autumn morning a few years back while I waited for the Queen and Dufferin streetcar, I saw some very handsome cyclists who appeared to be checking me out at the stoplight.


Allow me to set the scene for you. Queen and Dufferin is part of a very hip neighbourhood in Toronto where everyone has dewy skin, fashionable clothes, and somehow manages to look waifish, yet toned and healthy at the same time. I, however, did not look so fashionable and was usually bare-faced, in my crappy work clothes, and wearing my hair in a messy ponytail. As per usual, I cowered away from the fashionable crowd so they wouldn’t notice me, and as I moved away, I looked up and saw a cyclist with chestnut locks, gorgeous green eyes and a lumberjack bearded face staring at me. I called him Cyclist #1.


I stood like a deer in the headlights before immediately turning away to sit on a bench to collect myself. I was delusional. There was no way someone that hip and good-looking would ever check me out. I got up and coyly looked over my shoulder, but he was gone. Then as I walked onto the streetcar another hot cyclist at the stoplight turned around to check me out. What the hell was happening? Was I living in an alternate universe? I never got this kind of attention. Ever.


I got on the streetcar and processed the situation. It must have been a fluke. Maybe it was a full moon. Maybe they were assessing my hideous, outdated outfit.

“You are not crazy! They’re totally into you,” my friend Marcia said as we rolled cutlery at the restaurant where we both worked. “If you see them again you should ask them out!”

“I dunno. I never know when it comes to this kind of stuff. Maybe they were looking at someone near me?”

“No! They were totally checking you out. You need to have more confidence and put yourself out there. Go with your gut if you think someone is interested in you. C’mon, how many times have you been interested in someone and you’ve never said anything to them? Guys do that too. Assume, just for once, that someone is into you.”


Maybe she was right. I never made the first move when it came to dating. Guys can be shy too, so maybe they were actually interested in me. I had just moved into a new place after a really tough break-up, so maybe it was time for a new, more assertive Jenn. I’d also watched Brene Brown’s TED talk about being brave and vulnerable, and I’d been looking for an excuse to test it out.


I walked home from my shift that afternoon wanting to believe Marcia, but completely dismissed it. What had happened was a once in a lifetime occurrence. But lo and behold, within minutes of me stopping at the red light a cyclist had turned around to look at me. And so did another one.


It wasn’t a fluke. By the end of the walk five more cyclists had checked me out, and all my shyness was gone. I was on Cloud 9 strutting my stuff. This is what the popular girls in high school must have felt like! I flipped my hair back in the wind and sashayed all the way home. I was hot stuff and I was totally ready to make the first move…. At a later date. I wanted to soak up as much of this newfound attention that I could. So, for the next few days, I let hot hipsters on fixed gear bikes ogle me.


It had been so long since I’d been this happy and confident. I was doing really well at work and for the first time since my break-up, I wasn’t thinking about how devastated I was. After almost a week of being cyclist eye-candy, I decided it was time to make a move. I sauntered out the door to Beyonce’s “Run the World” and waited for a hot cyclist to come my way. Then Cyclist #1 appeared!


His blue helmet shone so brightly in the sun it practically blinded me and in the slowest of slow motion he turned his enchanting face my way. With every step I took towards him my smile grew wider and wider; however, with every step I took towards him, his smile grew smaller and smaller. I stood next to him within an inch of his face and he was totally creeped out and confused.


Huh? What? Why doesn’t he like this, I thought. “Um…I… Hi?” I squeaked. He stared at me completely perplexed that a non-hipster had the nerve to speak to him. I looked around frantically trying to think of something to say when I saw the wedding ring on his hand. Then I saw the wedding ring on the perfect, petite hand of the beautiful woman in front of him. She looked confused, creeped out and like she wanted to kill me in my sleep.


I looked around at all the other cyclists. Everyone on their bike was looking at the person behind them. And at the person in front of them. And at the people on either side of them. Cyclists hadn’t been checking me out. They were checking to make sure it was safe to go when the light turned green!


How could I have been that stupid? Why hadn’t I realized this sooner? Okay, don’t panic. Maybe Cyclist #1 was the exception. But judging by his facial expression it didn’t look like this was the case. “I… I… Sorry. I thought you were someone else.” I awkwardly laughed and stepped back. He gave me a laboured smile and peddled away faster than a doped-up Lance Armstrong.


So, that was my first foray into being assertive with men. Completely mortified at how delusional I’d been, I quickly reverted back to assuming that every interaction with the opposite sex was strictly platonic. Marcia thought I was going overboard and insisted that I keep trying, but the thought of living alone for the rest of my life with rescue dogs didn’t seem all that bad.


One evening the following summer, I was waiting for the streetcar and it looked like a really cute guy on a bike was checking me out.


No Jennifer! Stay away from the cyclist. Remember what happened last time? You just move over to that bench and wait for the streetcar.


But maybe he was interested. I wouldn’t know unless I gave it a chance. I turned around but he was gone.


The swirling pinks and purples of the sunset distracted me from feeling sorry for myself and how long the streetcar was taking. I took out my phone to take a picture when I heard, “Dayum girl!” A 70-something homeless man on a ramshackle bike looked me up and down. “Dayum girl, you look great.” He blew me a kiss and peddled away.


Well, at least one cyclist was in love with me.

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