Dating Chronicles

First dates — and bad dates — are a dime a dozen. But some are too juicy to take to the grave.


Michael and I hit it off online and then in person. The date went well. We met for Caesars on a Sunday. I had to cut it short as I had another date — whoops — and we met for brunch the following week. It was ok. I don’t know if I was ovulating or if it was the sunshine and chivalry of him picking up the tab every time, along with not trying to shove his tongue down my throat, but by the third date, I was tuning out. He talked about himself, non-stop. Was I that boring? Did he think he was that interesting? As a journalist, I ask a shitload of questions. It often puts people at ease and I can get to know them. When the tables aren’t really turned I do get bored. We’re all a little self-absorbed, no? Don’t get me wrong, Michael was nice but not what I was hoping for. He dropped me off in an uber and we kissed. It was super awkward — as first kisses can be — and I was tired. But upon entering my apartment, I immediately washed my mouth out. #NotAPromisingSign.

I genuinely liked Michael as a person. He was a gentleman and texted a week later: “If you’re not feeling it that’s cool.” I said I’d like to be friends and we connected one more time and I realized I couldn’t even be friends. I was so bored. So I added him on Facebook and that was that. Nice guy though. 6/10


I met Nick initially through a What’s App photo sent to me by his brother. When I realized he was ten years my junior, and part of my friend’s family, I declined. I had had enough Latinos for this lifetime (no offence to the Latin Lovers out there, just not my ‘ting anymore). And while not technically Latino by blood, Nick had been living la vida loca in South America for the past 8 years.

Three months later, Nick showed up to a friend’s party. He was in town visiting family. And he was damn cute and dangerously flirtatious. We spoke about he got bored but wanted try meditation (he knew I meditated with the host of the party). Upon listening to him jump around a number of topics in our conversation (he was sober), I told him to get out of his head as he seemed pretty cut-off from his body and meditation was about being able to neutrally escape the mind and focus on the body. He left the party with a stunning brunette.

The next week, at a festival, he came running up to me saying “You’re my favourite!”

“Favourite what?” I asked.

“Favourite girl. You’re so chill,” he replied. Still cute, I invited Nick to join a group of us to another festival that night. ‘Why not?’ I thought.

When he arrived, I let him know I was working the festival and he offered to stay until close so we could hang together. Then the temperature dipped and, dressed in shorts and a fleece, Nick left but kept texting me to meet up later. I declined. I was too tired.

A natural-born salesman, Nick texted me regularly to meet up. He only had one week left in town and, although I was fairly busy, I consented to a beer on a warm Wednesday night. He ordered me a Belgian beer and offered me some paid writing work. He then walked me home and we kissed. It was electric. I called him “peligroso” (dangerous) and walked away. He laughed.

The next night, my phone buzzed. I ignored it. Then it rang. It was Nick.

“Hey, I’m outside you’re house,” he laughed. “Well I think it’s you’re house. What are you doing?”

I let him in. He smelled nice. We talked. He had some writing leads so I listened (better to get paid then get laid). Then he started speaking about this Brazilian form of calisthenics. Intrigued I asked him to show me. He asked to borrow a t-shirt so he wouldn’t rip his tight button-up dress shirt, before he contorted himself around my tiny living room floor. I sat perched on my IKEA sofa, perplexed. He moaned and grunted, “Oh this one is so good — it’s my favourite.” After he humped his way across my floor doing the breakdance move, the worm, his nice-smelling cologne gave way to a sweat that was turning me off.

Then it was my turn to try a stretch-a-thon. I have to admit, it felt good. We laughed. When I returned to the couch, he leaned in for a kiss. It was much more aggressive than the delicious goodnight kiss we shared the evening before on our bikes. But after a few minutes he started squealing like a girl about how sensitive he is I wasn’t sure the next move. Kick him out? Or keep going? I asked about the mysterious brunette. He said he actually doesn’t like getting intimate with too many women. Good line? Or small penis?

He stayed. After a 20-minute long gentle fellatio session for him, where I had to place a pillow over his face so my neighbor wouldn’t hear his shrieks of sensitivity, I started to wonder if he had had sex earlier — hence why he was so sensitive. After he came and cleaned up, we spooned all night. For a talk-a-holic, he was the soundest sleeper I had met.

It was sweet.

We shagged in the morning. He told me later he had changed his flight and would be around to chill more before he left. I never saw him again. But he did text. So, I’m not sure if I was played but his brother did mention in passing that he’s looking for a girlfriend and doesn’t sleep with that many women. But, jaded as I can be, I believe all men will lie to cover a bro’s back. Nick did invite me down south, but it seemed more out of politeness. Like many Latin men I’ve encountered, Nick is more of a gentleman player than many of the dogs in the northern hemisphere — knowing how to put a woman at ease, even if it is to score and steal away. Rating 7/10


Jimmy was sweet. Tall, shaved head with a soft Irish lilt. He asked the right questions and didn’t try to kiss me on the first two dates. When he managed to invite himself over for dinner (I don’t cook) and to listen to some of his records (he lost the record player in the divorce), I was impressed by his bravado.

He arrived on the Sunday night after texting he’d be a half hour late. That was fine as I was stressed in the kitchen. When he arrived, however, he had no records.

“I didn’t want to bring them in the cold,” he said.

“Oh, did you take transit?” I asked?

“No I drove,” he said. “But I brought some beer.” Perplexed I let him in. He picked some vinyl from my limited collection and we talked. I managed to make a decent meal and, over dinner conversation, he mentioned he had left his dog at his ex-wife’s house. Was this a hint he was able to spend the night? Traditionally the third date is the time to foray into the physical. And the following day was a holiday Monday.

Ten minutes later he awkwardly griped how his ex went to bed early and he’d have to collect the dog “at a decent hour.” OK, no sleepover, I thought — which was a relief, as I didn’t want to move that fast — we had not even kissed.

Dinner finished and Jimmy was discussing his quick money app idea. It was pretty weak. I politely tried to point out the holes. I was honestly starting to lose interest. I made the guy dinner, after he invited himself over to listen to records that he didn’t even remember to bring, and it seemed like his ex still had him by the strings. IF he was into me, he had to make the move at this point I reckoned. While clearing the plates, I spied the clock.

“It’s 9:45 pm,” I said casually. “What time do you have to get the dog?”

Jimmy, who had either lost track of time or presumed I was kicking him out, got up mumbling “yeah, I should go.” He got on his parka and boots and opened the door. It was the moment of truth: was he going to kiss me?

Jimmy stepped into my hallway, turned around, and awkwardly raised his gloved hand. “Well, bye,” he said sheepishly. “Thanks for dinner?”

“Bye,” I said. “Keep in touch.” I never heard from him again.

A family friend, whose husband is painfully shy, said she believed he was too nervous. Her spouse agreed, saying he wouldn’t have kissed me; he’d have been too shy. While I wasn’t too shattered, I was pretty taken aback by how quickly he went from being so confident and self-assured on our first two dates to cowering into a pre-pubescent mess. I guess liquid courage wins. 4/10

The Firefighter

After a stormy break up with a summer romance, I headed home early on Labour Day weekend. I had a music festival to cover and was going to overnight on a friend’s boat to make up for my cottage weekend cut short.

Our boat neighbor, a friend of ours, was smoking pot. Not realizing how strong it was, I took a small pull to ease the stun from the previous 48 hours. Then a happy smiling couple, matching my Cheshire cat grin, appeared out of the bush. Fittingly, they were going to the same festival that I was. High as a kite, we all stumbled to our bicycles and headed to the party.

Inside it was fun. I ran into some colleagues and then followed the happy couple into the dance pit. They were sweet and kind. The guy put me up on my shoulders (I am a muscular 135 pounds and was impressed). It was fun and a good core exercise.

Upon returning to the ground, I started feeling a guy rub up against me. He was alright looking, I was high and getting fed a steady stream of ciders by the happy husband, and consented to the gyration. With about 20 minutes left in the concert, we — the young, gyrating fireman and I decided to exit early and make out. We found a bush. It was by the water’s edge and had a wood-chipped ground. We got busy. He lay down. I straddled him (not recommended on wood chips!) and we got it on. He was 26 and on MDMA. And his friends kept phoning to find him. He kept ignoring the calls and telling me how hot and sexy I was. It was pretty hot, considering the impromptu location and his inability to come. That was until some asshole came in the bush to pee — a foot away from this firefighter’s head.

“What are you doing?” I yelled? The peeing Jon just looked over and kept peeing. With the likelihood of sprays hitting my sex toy’s head, not to mention the lack of privacy, we shuttled over ten feet to finish off. Firefighter called him a Peeing Voyeur. We laughed. But it dawned on me where we were and I secretly shuddered to think how much urine we were probably fucking on.

Upon shaking the dirt off my knees and fixing my clothes, he took my number. I have no idea if it went in right. I was too wasted. But he said he definitely wanted to see me tomorrow night at the concert. We said goodbye. I somehow managed to find my bike and make my way back to the boat. I went straight to bed.

The next morning I woke up to bruised knees and a series of pink itchy bites along my inner calf and on my breast. My breast? There was dirt on my neck and a big bruise — did he strangle me? No, I remembered, he was a biter. I cleaned up in the calm lake water. It helped to quell the itching and made me feel less dirty — in some respects. A fellow nudist bather was about 50 feet away. I had to go back to the festival that afternoon and I remembered that the firefighter wanted to meet up again. I checked my phone. No missed calls or texts. I was a bit relieved.

When I got back to the city on Tuesday I went straight to the doctor.

“It could be poison ivy,” she said. I explained that it was itchy but not unbearable and that there were no fang marks like the other spider bites I had from the boat. When I mentioned I had washed in the lake, she said that was a smart move. Apparently lake water is the best way to treat poison ivy. Thank god.

The marks eventually disappeared over the next three weeks. I never heard from firefighter. I wasn’t too surprised — he was high and likely completely traumatized by getting it on with some woman in a dirty bush with a Peeing Jon or, my worst fear for him: he had the same itchy rash all over his butt and dick. Sorry, dude. I guess you can’t put the fire out of everything. At least the sex was hot.