Exploring the ins and outs of the online dating world



The 27 of 2017: The Final Peek

The 27 of 2017: The Final Peek

xx The 27 of 2017 is the idea behind the book I am writing. This will be the last public post of the series, but after that, you're hopefully going to be able to read these stories as a whole in a book (down the road, I have a lot of work to do on it). This last post is really important in the story of that year xx

You know how that ends. Newly single girl goes on eighteen dates before anything really sticks and somehow, the timing of life can be so eerie. Andrew and I left Montreal the same day. I went back to the East Coast for a childhood friend’s wedding with a planned stop in Halifax first to see Kieran. Kieran and I had got back to where we were before that moment and kept up a strong friendship for the year that I had been away. There was still a lingering curiousity that neither of us could deny that brought out a hopefulness in me that muted the spiraling thoughts of Andrew in my mind.

In a hammock on the waterfront of downtown Halifax, I had Kieran’s pants unzipped, sucking on his erection. That’s where a night of dancing, drinking, and old friends led us. The night let the group dwindle to just the two of us, as always, and in our usual fashion, we got up to no good. Drunkenly, with my heels on the ground, legs spread and arms holding down the sides of the hammock, so we wouldn’t be swallowed by the edges, I slid my tongue along his shaft. Forget the foot job, this was the best sex related workout I had ever experienced. Core tight, we heard voices coming closer and I grabbed my heels on the ground and Kieran’s hand. Fumbling out of the hammock, Kieran erection still in full, we walked up the hill back to the hotel, playfully touching, and pissing ourselves laughing. I gave head on the waterfront in a hammock in public and almost got caught; Andrew was the last thing on my mind.

Even after all the heartbreaks, disappointments, and unexplored avenues, I still believe in the goodness of love. I believe in it every time I go to a wedding and feel its presence and happiness all around. I believe in it when I see an elderly couple holding hands along the street. I believe in it when I feel the world blurring around me when I'm with someone. Sometimes in the pressures and flux of dating, I forget its purpose. I'm not just after great sex but you better damn believe that I want it. But I want more - so much so that I had to tattooed onto my skin. I want more in life and more in love and I still believe its out there. I'm not a patient person and with too many first dates gone awry, the purpose of this whole online dating world sometimes becomes unclear.

Guy after guy, date after date, I struggle to believe that there is something more out there waiting. But then I think back to that date after heartbreak. It was far too soon after, but it turned into a whirlwind summer of some of my favourite memories. I remember my faith being restored as he turned back after I called out his name. I remember my faith being restored after smiling like an idiot in public to a cute message. I remember my faith being restored the moment I was at my childhood friend's wedding in the summer.

As I watched them intertwined, looking at each other lovingly while dancing together for their first song, my friend Michelle’s mom stepped closer and gently squeezed my shoulder.

“If it’s meant to happen, it will work out.” She said softly.

The tears building crept down my cheeks.


Kieran ended up moving to Montreal, along with my good friend I had known since kindergarten, Michelle, the following month. Obviously, everything crossed my mind. I wanted to know where things would finally go now that we lived in the same city again. Andrew was still at the back of my mind, but I knew I had to, as he taught me, live in the moment and say yes to new experiences. I remember the first time he told me that “saying yes has lead me to some of the best moments” and since then, I knew that, along with the memories, he helped me develop a new motto that I truly embraced that summer. So, I said yes to it all.

“Kieran!” I squealed as he wrestled my arms down and began squeezing my sides.

I wiggled my arms free and pushed Kieran down and got on top of him. My hair draped on the pillow next to him as I hovered myself right over his lips and brushed my bottom lip against his. He slightly groaned and then smiled. His arms wrapped around me, he rolled me over and nibbled at my sides. I burst into laughter and squirmed around with my arms still wrapped around Kieran, not wanting him to let me go.

“Is this what it’s always going to be like?” Kieran said with a smile.

“It better be.” I said, tugging at his belt with a grin.


Being the only other person in the city that both Kieran and Michelle really knew, we created a trio. I had two of my closest friends in what started to feel like more of a home, and I couldn’t have been happier. Somehow, in the midst of the chaos of my final internship, we would find a way to hang out a few times a week.

It was one of those well-crafted evenings that Noah and I had perfected. A glorious trifecta of booze, board games, and snacks. Noah, off eating nuggets or playing Mario Kart with boys, wasn’t there; I wish he could have saved me from feeling like a third wheel. I have no memories of what happened that night before this moment.

“Okay, here is the handshake.” Kieran laughed.

“I’m ready.” Michelle replied with a smile.

I sat there watching as the two of them playfully tugged and prodded at each others’ hands while giggling. Wine glass in hand, I pulled out my phone, I sent Andrew a message.

“Ahh I miss you, Andrew.” I sent.

“Aw! Anna. I miss you too.” He replied a few minutes later.

“You’re incredible.”

“You’re such a sweetheart.”

“I can’t help it with you.”

“I’m okay with that.”

My smile drained as I looked up from my phone and watched Kieran and Michelle continue their trial and error at making the perfect handshake. I have no idea why they were even making it or how I ended up the one sitting alone.

“Well I have class in the morning, I should get going.” Kieran said, looking over at me.

“See you later, bud.” I said coldly.

Kieran waved goodbye to both of us and as he left, I felt a sinking in my stomach knowing what I was going to say.

 “I hate to bring this up, but do you like him?” My voice shook as I asked.

“Who? Kieran? Oh my god, no.” Michelle shockingly responded. “I don’t even find him attractive.”

“I’m sorry I had to ask. I felt a bit uncomfortable tonight, like a third wheel, and I just wanted to make sure.”

“I swear, I don’t even think he’s cute.” She paused. “I know how much you like him.”

That weekend, the three of us went to mine and Noah’s usual spot. I walked in and gave my usual flirtatious smile to the bouncer I knew as he asked me to open my jacket for a search. As we got upstairs, Kieran kept his arm around my waist as we had a drink, gently gliding his thumb back and forth.

“It’s usually busier around this time.” I said, looking out at the almost empty club with music still blaring. “Screw it.”

I grabbed Kieran’s hand and motioned them both over to the dance floor. We all started dancing on the platform, green and red lights shinning across our faces as the few people in the place watched. And we continued to dance as more people came in until the place became packed an hour later.

With Kieran’s arms around me, my mind flashed back to when I was last here. The image of my hands pressed against Andrew’s chest as he swayed back and forth with me was all I could see. I pulled away from Kieran and walked over to the bar. I took a large breath and watched as Kieran and Michelle continued to dance and motioned me back over.

I felt like I was observing the entire club as a distant spectator. Peoples’ faces plastered with playful smiles or at least ones that held up that illusionary tale. Michelle and Kieran were among those. They looked so innocent and fresh-faced as they pulled every uncle at a wedding dance move from their belts. I wondered if that’s how I looked every other night I came here, without the terrible dance moves. Just like that, I felt instantly detached from the situation. All I could think about was Andrew.

“I have to go. I’m sorry.” I said walking over to Michelle and Kieran. “Go have fun.”

“Anna, what’s going on?” Kieran shouted as I walked away.

“You’re going to be okay, right?” Michelle said catching up to me.

“Yes. Please let me go. I’ll be fine. I just need to get out of here.”

“Okay. Text me when you’re home.” She said hesitantly.

I walked out of the club and looked around at what felt like unfamiliar streets. Crawling into bed, I felt an emptiness from the spot to my right.

“My head is spinning so much right now.” Michelle messaged me the next morning.

“Haha hung over?” I replied.


A few minutes later my phone buzzed again.

“I think I’m the biggest idiot ever and thought Kieran was a guy I was dancing with last night and kissed him. I’m so sorry. I don’t even remember it and completely thought it was the other guy. I’m so stupid and I feel awful.” She sent.

I stared down at my phone and crawled onto the bathroom floor. I rocked myself back and forth knowing that in just a few minutes I would have to get up and get on with lesson planning. I stared into the mirror with a numb expression on my face that I carried to work for the rest of the week.

Kieran stopped by later that night to pick up his bag that he left the night before. My eyes puffy and red, I brought it up to the door when he arrived. I didn’t say anything and handed it to him.

“Anna.” He paused. “I hate seeing you like this.”

I looked at him and walked back inside without turning back around. I couldn’t even imagine looking Michelle in the eye.

 “It didn’t even seem real.” I said blankly at Dr. Brooks. “It still doesn’t.”

A few weeks later, I went on a date with a man named Andy. All I remember is going for a short walk around the neighbourhood, sitting in front of a church, and then him on my couch with his clammy palms sticking to my hair as he kissed me. With his clothes starting to come off, tears poured out of my eyes, and I asked him to leave.

Every Word I Lay

Every Word I Lay

The 27 of 2017: Skipping Ahead Continued

The 27 of 2017: Skipping Ahead Continued