A Most Perfect Weiner

I’ve never understood people who make these grand proclamations that they have no regrets in life.

I have thousands of regrets.

I can name three from last night.

One occurred while lying in bed, engaging in pillow talk with a medical anal suppository, prescribed by my doctor to treat my colitis.

Ten minutes before midnight I uttered “It’s just us tonight, buddy,” as I took a deep breath and felt it dissolve in my anus.

He said nothing, as most glycerine-based corticosteroids tend to do, but it doesn’t mean I wasn’t hurt or that I regretted starting the conversation.

My prescription medication, like most men I’ve dated, reinforced the prevalence of emotional distance in our society.

My life regrets operate on an ever-shifting continuum. Some seem less egregious as time goes on. Others stick like gum.

Of all the idiotic men who have graced me with their presence over the years, none hold a candle to Dennis, a 33-year-old, blithering, closeted bisexual with an alcohol addiction and the most beautiful sausage I have ever seen. (You’re welcome, Dennis)

Trust me on this one. I’m operating from a colossal sample size.  

And it does take a lot out of me to hand over credit to someone else in the physical attribute department.

My anus has been my muse through the better part of both my books.

I once told my therapist that it was exceedingly difficult for me to stay grounded with such a flawless ass. He told me he couldn’t really relate but appreciated the unbridled honesty.

The day I met Dennis was the same day I inflated a children’s pool on my apartment balcony and filled it with pool noodles. I had invited over 20 people for a pool party without clarifying what type of pool I had access to.

Several people entered my condo perplexed at the site of Ben and I drinking margaritas to tropical island music.  

One of my exes entered my condo, rolled his eyes, and said, “See, this kind of shit is why we’re not together.”

Here’s a photo if you think I’m a filthy liar:

The “pool party” concluded around 4 p.m. I drunkenly used a sump pump to drain the water into my shower. I passed out in my trunks an hour later and woke up at 8 p.m. to a text from Ben that said, “How many Weight Watchers points is ass?”

I smirked as a wave of immense gratitude washed over me, recognizing that I had a best friend who completely understands the universe’s most pressing questions.

I stayed in bed and sorted through my Grindr inbox.

The first message was from a man who was a “life coach.” Oh, that sounds recession proof.

Another was from a publicist, a profession I briefly dabbled in. He opened with a photo of him naked on all fours, with a perfect line of sight to the eye of the storm. I wondered who took the photo or if he set up a tripod.

I can’t imagine summoning Ben over to white balance before shooting a photo like this.

A publicist in general is a strange profession. Who grows up and has big dreams of making someone else famous?

A third message was from a guy whose profile indicated he was looking for “Pokemon Go enthusiasts.” I’ve been playing a different form of Gay Pokemon for years on Grindr. Gotta catch ’em all … strains of HPV.

Another was from a gent past the age of 65 who offered me a “generous lifestyle as a houseboy.”

I’ll probably have sex with a geriatric one day just to hear them dirty talk to me in Latin.  

“Lorem Epsum Homo Analingum”

The only remaining suitor had no photo, describing himself as “very discreet, party boy, well endowed.” It turns out my dinner that evening would be the human equivalent of table scraps.

We started chatting for the better part of 40 minutes. He was aggressive, inebriated, and hilarious, a retired frat boy with Peter Pan syndrome to boot. I had been missing a man whose banter could rival my own since my ex, Patrick, had  left the picture.

My interest was piqued — I invited him over for a drink around 10 p.m.

Upon his arrival, it quickly became clear we were in different states of mental clarity. I barely had a buzz, conversely he was barely managing “TH” letter combinations.

Dennis was banker douche incarnate.

He was dressed head to toe in a Hugo Boss fitted suit and wearing a white collared shirt with lipstick stains on the left and beer stains on the right.

His eyes were puffy and bloodshot but beautifully blue, the kind you could easily point out in a lineup.  I will forever be a sucker for dark hair and ice blue eyes (in case you’re reading this and looking to spend your life with me).

Dennis was ruggedly handsome but a shape-shifting chameleon as he walked under my overhead lighting.

He was the kind of guy who, if you caught him on a good day, could be John Hamm, and on a bad day, John Goodman.

Our physical attraction did not wane our entire sordid love affair.

“Your eyes are insane,” I said, handing him a glass of Merlot.

“Thanks dude,” he said, aggressively gripping my ass. “You are fucking gorgeous.”

“More gorgeous than whomever is still on your collar?”  I asked, pointing to the lipstick stains.

“Yes,” he said. “Why do you think I’m here and not at her place?”

“I’m going to guess variety,” I said. “I can already tell you have the attention span of a clown fish. But I’m flattered, dude.”

“I’m kissing you now,” he said, placing his glass of wine on the coffee table.

“Deal,” I said, pulling him in by his silk tie.

We made out naked to Kings of Leon for the better part of an hour half. Dennis was a fantastic kisser who I imagined could only get better once his blood alcohol level came back down to earth.  

Sidenote: Bad kissing is irredeemable in my book, and should always be followed with the phrase “ good luck in your future endeavours.”

As Dennis continued to grind on top of me, I stopped him and said, “Is that a Transatlantic Pipeline in your pants or are you just happy to see me?”

“You’ll see,” he said, smirking as he ran his hand up my ass crack where a small pool of sweat had formed during the frenzied makeout..

“Fuck,” he said. “You are soooo wet.”

“What do you mean?” I said.

“You’re turned on,” he said. “I love it.”

“Have you been with a lot of men sexually? I said, confused. “That’s not how that works.”

“Whatever,” he said. “I dig it. The wetter the better.”

“You should see me after a jog,” I said, ripping off his shirt and dragging him to the bedroom. “I am a disgusting piggy.”

We ripped off our remaining clothing and began aggressively making out on my floor. I couldn’t see much so I kicked the floor plate of my lamp to turn it on. As the bulb hit 50 watts I gasped at what lay before me.  

A sexual organ with the potential to procure a Nobel Peace Prize.  

Eight inches, uniformly pink, consistent shape, flawless angles and velvet smooth to the touch.

It was the kind of penis that UFOs would enter the Earth’s orbit for.

If you ever catch me daydreaming on a lily pad one day, you’ll know what’s on my mind.

“I feel like I want to cry,” I said with it in my palm.

“Cry?” he said.

“I’ve been touched by the penis of an angel,” I said. “Just give me a moment of silence here.”

“It’s not that big,” he said.

“I said silence,” I replied. “Who created this? It goes the Mona Lisa, The Last Supper and then this.”

“Wow,” he said, laughing. “You are fuckin’ ridiculous, Jordan.”

We stayed in bed until 4 a.m. laughing that over my reaction. We never actually had sex or anything beyond second base.

I was shell-shocked at the final confirmation of my homosexuality. It was powerful and made me reconsider my take on The Alchemist.

Dennis’ penis was like a prized antique car that belonged in a secure garage away from the threat of nature’s elements and covered in Turtle Wax. I couldn’t risk the chafing.

Dennis and I embarked on a sexual relationship every Friday or Saturday, past 2 a.m., for the entire summer. Like clockwork, one of us would message the other around last call and rendezvous at the apartment I shared with my best friend, Jesus.  

Our chemistry was electric but it was also undeniable to both of us that we were totally falling for each other. He wanted to be my boyfriend and I couldn’t bear the thought of losing his member.

Ok, I liked him too. However if he and his penis were conjoined twins and I had to kill one to keep the other, he would have been toast.

Dennis and I shared sides of us that neither allowed others to see. Two hopeless romantics guarded beyond repair.  

When he was sober, he was boyfriend material.

When he was drunk, he acted as if all the blood in his brain had travelled downwards to service his water-buffalo cock.

One Sunday night, three months after knowing each other, he called me near tears and said, “I fucking like you so much, but why do you like me? You could go and get with any guy in Toronto.”

I said, “But I like you too. This isn’t a good look for you, Dennis. I wouldn’t sneak around with you if I didn’t have strong feelings for you. So why are you freaking out?”  

“Because I’m not coming out. I want a wife and a family. I’m bad for you and you’re bad for me,” he said.

“You’re being dramatic,” I said. “I’m having a good time, why don’t we just continue this until it’s not fun anymore?”

“It’s going to end badly,” he said. “Let’s just end this now.”

“If you want to,” I said. “But just know that it wasn’t me who ended it, man.”

That should have been the moment Dennis and I went our separate ways. I had romanticized the idea of us as something that had a chance, but in fact, we were nothing more than the conflation of our emotional baggage.

As Dennis began to miss me, his drinking increased tenfold. As weeks passed he would leave me voicemails at 4 a.m. that were indecipherable. I ignored them.

One evening Jesus found him pacing by himself behind our apartment building in a full suit. He invited him in to see me. I was lying in bed in sweatpants with a green algae face mask on.  

He was so shitfaced he started to cry on my bed. I washed off my face mask and laid beside him on the bed. I had learned all too well that with being gay comes a complicated life. I gave him a bottle of water and stripped his clothing off before falling asleep beside him.

At 4 a.m. he woke up and went to the washroom, naked. I heard him first rummaging around before hearing his piss stream. Then a minute later, the next noise I heard was Jesus screaming for his life. 

Dennis had come out of the washroom in a drunken state, turned left instead of right, and crawled into bed with Jesus.

I imagined the experience from Jesus’ point of view. A mumbling predator enters your room in the dark of night in the nude, smelling like Hennessy and spooning you, the only consolation being the soft silk penis grazing your ass cheeks. Terrifying.

When Dennis came back to my room I nonchalantly turned over and asked, “Did you just crawl into bed naked with Jesus?”

“Yes,” he replied.

“Accidentally?” I asked, entertaining the fact that anything was possible with him.

“Yes,” he replied.

“OK then,” I said. “Good night.”

The next morning we had sex and he left.

Two days later, I was working on a presentation with my business partner when he asked me why I kept wincing and grabbing my dick.

“I don’t know,” I said. “It feels like fire ants in my urethra.”

“Oh no,” he said.

“What?” I asked.

“Dude,” he said. “I think your ways have finally caught up to you. You totally have an STI.”

“No I don’t!” I yelled, in total denial.

I went to the washroom to pee at least seven times before lunch. On the seventh visit I looked down and screamed.

I walked back to the office, turned to my business partner and said, “OK either I just jizzed myself or your guess is dead on. Fuck Fuck Fuck Fuck.”

I took an Uber to a walk-in clinic seven blocks from my house and told the receptionist I was “peeing fire ants.”

“How fun for me,” she said.

She handed me a plastic cup to pee in and sent me to the washroom. When I handed it back to her, she took one look at the floaters and said, “Listen, I’m not allowed to give medical advice but I think you know what this is.”

“It looks like sea monkeys!” I yelled.

The doctor took me into a side room to let me know that it was either gonorrhea or chlamydia but we wouldn’t know until the tests came back in three days. She treated me for both with a handful of pills and a needle to my upper arm. Then she started into a lecture about safe sex.

“Let me just stop you right there,” I said. “I know who this is from and I used a condom.”

“During oral too?” she said.

“Excuse me?” I said. “That is not a thing.”

“You should always be performing oral sex with a condom, Jordan,” she said.

“Are you trolling? I said. “I don’t care how many times you tell people to do that, because you probably have to, but no one is really going to. That’s probably the best tip I’ve heard for dying alone.”  

“Well then you could get this again,” she said. “In the meantime, no sexual relations for seven days and you’ll have to let your partner know.”

“Oh I’m already texting him,” I said, looking up from my phone. “And I’m using a lot of fire emojis, to represent my scorched penis, and eggplants. The eggplant is for him. Ok now, do you think the gun emoji is too much?”

“I think so,” she said.

When Dennis didn’t reply to my texts I called him.

“I’m in a meeting,” he said.

“This will only take a second,” I said.  “Anything you would like to share with me, Dennis?”

“What?” he said. “No, nothing Jordan.”

“Then where the fuck did I get this STI?” I said. “How many other people are you sleeping with?”

“STI? Why do you care how many people I’m sleeping with?” he said. “Why is that your problem?

“BECAUSE I’M PISSING FIRE,” I said. “My cock is the catacombs of hell.”  

“I didn’t give it to you,” he said. “I feel fine.”

“You’re asymptomatic,” I said. “I’m not sleeping with anyone else. I can handle simple logic, Dennis.”

I sent Dennis to the same clinic to see the same doctor.

Two days later I got a call from the clinic regarding my full STI screening.

“Hello Mr. Power?” said the woman on the other end of the phone.

“Talk to me babycakes,” I replied.

“Mr. Power I regret to inform you that you tested positive,” she said.

“What?!?!” I said, fearing the worst.

“For chlamydia,” she said.

“Oh whew,” I said. “That’s a walk in the park. That shit is basically trendy at this point. I mean are you even living if you’re not sharing a fun scare at brunch.”

“Umm sure,” she said.

“You really need to work on your telephone manner,” I said and hung up the phone.

I texted Dennis to let him know and he replied with, “Yeah I know, I got the call.”

A week later, with a refurbished dick, I agreed to meet Dennis for dinner at a restaurant called Marben in Toronto.

My masochism knew no bounds. I blame Botox. I don’t even recognize the animal I become once my Botox starts wearing off.  

That night, we killed two bottles of wine and two porterhouse steaks and then went to Portland Variety on King Street West to sample bourbon.

My office was just across the street, so I took him upstairs around 1:30 a.m. We immediately started ripping off our clothes and making out on my desk.

“I’m not having sex with you tonight,” he said. “This has to stop.”

“Shut up,” I said. “It’s the least you can do for breaking my clean streak.”

“So you’ll let me in your ass but you won’t let me in your heart?” he said.

“Well when you put it like that,” I said.

“I’m serious,” he said.

“Dennis, there is no future,” I said. “It’s obvious we can’t keep our hands off of each other but I can’t exactly see you at the Pride parade anytime soon.”

“What if I told someone?” he asked.

“Who?” I said.

“Well I told the doctor,” he said.  

“A person who is bound by confidentiality?” I said. “How brave.”

“It’s a start,” he said.

“Listen I’ll support you but do not come out for me,” I said. “Come out for you. I don’t want that burden on me.”

I knew Dennis and I would have sex that night. I’m the Yoda of cock. I just didn’t know the foreplay would start beside a Xerox machine.

The next morning we packed his car and drove up north to go skiing at Blue Mountain. Because he was forced to stay sober, he was his best self, right up until the self loathing creeped in around noon.

At lunch, he drank two large pitchers of beer to himself, which was a tacit implication that I would be driving home.  He lasted four more runs, falling on two of them and then asking me for a handjob on the chair lift, which I denied.

We left around 3 p.m. with me driving his Toyota Camry.. We stopped at a service station and he ran in to grab food.

I fumbled around looking for my phone and opened the console. Inside the console was a white envelope for Erythromycin, with dosing instructions written in pen: “4 times daily for 7 days.” The envelope was full of medication.

When Dennis got back to the car I completely lost my shit.


“What?” he said.

I held the envelope up.

“Oh,” he said. “ Yea, I took it this morning, I’ve had a busy week and I’ve been drinking a lot.”


“Oh,” he said. “Well I told you I didn’t want to.”

“BECAUSE OF THE CHLAMYDIA?!” I yelled, while slapping him across the face.

“Ow! Fuck! No, I forgot about that,” he yelled back. “I just meant in terms of the feelings getting messy between us.”

“You forgot about an STI?” I said.

“Yeah,” he said. “I have a lot on my mind.”

“OH…my…god. Why didn’t they give you the single dose?” I said. “This is like special sexual education. What grown man forgets to take medication to cure him from an STI?! Were you overcooked in the womb?”

Monday morning I went back to the same clinic. When I told the same doctor what had happened she sighed.

“Jordan,” she said. “If you can’t trust a person why are you sleeping with them?”

“I don’t know how to answer that but let’s settle this right now,” I said. “His name is Dennis Walters and he is also your patient. Look it up on the computer. Blue eyes, big cock, you can’t miss him.”

“Jordan, I can’t speak about other patients,” she replied.

“Well I can Doc, “ I said. “D-E-N-N-I-S W-A-L-T-E-R-S, there will be more victims of his stupidity. Let’s call him right now on speaker.”

“You know,” she said. “This might not be my place but if a man can’t be bothered to concern himself with your health, he doesn’t really care for you.”

“I don’t think he’s a bad guy,” I said, as guilt filled my soul. “He just gets too drunk all the time. He probably thought the vodka would kill the infection.”

“Listen,” she said. “It seems you have imagined a different person than Dennis really is. What is your favourite thing about him?”

I paused, at a loss for words.

“Maybe his personality?” she asked.

“Sometimes,” I said “But frankly I’ve had more in-depth conversations with Siri.”

“On a scale from 1-10, 10 being best, how would you relate your relationship with Dennis?” she asked.

“I’m drawing a blank,” I said. “I only thought of 8 because that’s the number of inches of his penis. Oh no, I feel an epitome — I guess I don’t actually like Dennis, doc. I’m dickmatized!”

“I don’t know what that means nor would I like to know,” she said. “But it seems you’ve realized you need to end your relationship with this man.”

She then handed me another round of Erythromycin.

“Oh, hello old friend,” I said as I swallowed the pills.  

That evening Dennis came to my condo and we vowed to never see each other again. We stood in my hallway and held a two-minute hug before saying goodbye for what we knew would be forever.

For weeks, I played “All Too Well” by Taylor Swift as I ran through the highlights of our time together.  (Great song guys)

A year later, I got word over brunch with a friend that Dennis had moved to Manhattan. I was unfazed by the news and knew the spell had been broken.

But, I wasn’t out of the water yet when it came to my dysfunctional relationships with men.

Case in point: As we settled up the bill, my friend described the behaviour of her stalker.

Without hesitation I replied, “Honestly, that sounds kinda nice.”

A week later, I was back in therapy.


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