In 2019, after finally coming out of a series of long-term relationships, I decided to jump into the dating world with my first experience using dating apps. I had no problem fucking guys, regardless of how shallow I thought they were -a shallowness I was sharing with them, back in these days. It was so easy: it only took a pure physical attraction and voila. Of course, when you look back, this wasn’t really a win-win situation. The guy I ended up with was probably the least-worst of them and we still ended-up being absolutely incompatible with each-other. It ended up being so toxic, actually, that it gave me PTSD of the other sex and made me completely shut down to the idea of ever being in a relationship again.
On my round the world, I was all-in to welcome someone in my bed for a night, but the idea of even remotely giving a guy access to my life, back in Montreal, was a big no-no. It’s not really that I didn’t trust the opposite sex, it’s more that I didn’t trust myself. If I had let that previous relationship, that was unbelievably unhealthy, go on for that long- what was it to say about my judgement when I was in love.
What that relationship had thought me, is that, I had absolutely none. I had no judgement and I had no standards. Suffice for you to be tall, hot and funny and regardless of if you had the emotional stability of a toddler: I was hooked. Bonus points if you had tattoos. It felt like I was color-blind to all the red-flags that WERE pretty obvious since day 1. I just kept pushing it and committing more and more to the idea of the relationship I wanted. And the more I committed, the more I excused the harmful behaviours, creating a whole narrative around it, to justify why I was putting up with it -until it was so noxious that I couldn’t lie to myself anymore.
When I finally started to gain back some judgement, it slapped me in the face how much I had let things passed that I had never judge acceptable before. I swore to myself that I would never ever let that happen again -but unconsciously, I think that the solution I found was just to not let anyone in my routine, at all. It’s like if instinctively, I knew that there was a chance to lose my common sense if I did, so instead of working on boundaries, I just shut down the potential risk entirely.
With now two years of flings only in other countries, with men I knew I was never going to see again- It didn’t took too much introspection to realize that if I kept doing this, I would eventually become afraid of commitment and slowly turn into a feral cat-lady. I knew I had to do something. So, early August, I decided it was finally time to start dating again. I mean really looking for it- not just waiting that it magically falls from the sky.
It was not long before the discouragement settled in.. 15 minutes after downloading all the apps, to be exact. I had scrolled through a bunch of profiles only to realize that absolutely no one was interesting to me. I am talking about men holding fishes. Taking pictures shot from below. Holding a kid on their shoulders, a beer in the right hand, a cigarette in the left. None of them were smiling. Most of them had no words in their profile- the ones that did, had a whole fucking essay that already betrayed the fact they were problematic. I knew the app wouldn’t cut it, this time. Not after being back from trips where you meet people organically. There was no way for me to lose time (and hope) by swiping through thousands of profile only to possibly find one that might be cute in picture but a total no-go in real life. There had to be a better way.
That’s when I thought about my AI best friend: ChatGPT.
I wrote on every of my dating apps profile to come reach out to me on Instagram and then I use ChatGPT to send a series of questions to whomever was reaching out in my DMs that I wasn’t following back. The first question was setting the tone for the following four. Depending on the answer, the requester would be put in the category “fuck boy” or “potential boyfriend”. Spoiler alert: no fuck boy contender ever made it to the last question. It seems like if you are only looking for a pussy, even 5 questions is too much commitment.
That brings me to how much surprise I was when several guys looking for a long-term partner agreed to play the game, answered all the questions with humour (and the right answers) leaving me with three potential dates. Of these three, one ghosted me as soon as I asked to meet-up (I did not had time nor the interest to entertain small-talk for weeks before meeting) and two scheduled a first date for the next weekend.
My first date was with a guy who we will name Paul. Paul had answered all the questions from chatGPSteph with humour, laughing in cap-locks in-between each of them. He was good-looking, smiled in every single one of his pictures, had his own company and seemed funny, wise and positive. He was covered in tattoos (not necessarily something I was looking for, as it threw me back to my ex’s look) and had shoulder-length blond hair. We were going to meet-up the next Friday after work, around the Atwater market- and go for dinner. I had no real hopes going into this, but I still took time to select an outfit I thought would fit his vibe and after feeling cute and ready, I walked to our meetup point.
When Paul arrived, the first feeling I had was that I wasn’t really attracted to him. He wasn’t bad looking but he wasn’t doing it for me, I guess. He was talking very fast, too, which I found a bit unsettling. He had such a positive attitude though, that I was sure I would enjoy my night anyway. We started talking and the more the conversation went, the more I started to find him attractive. He was funny and confident, had a very hard past that he was able to use for self-growth and it was obvious that he was now emotionally and financially stable and independent because of it. We finished the dinner and Paul asked me if I wanted to continue the evening in a bar nearby, which I answered yes to - I was now feeling a possibility for more than friendship with him.
The more the night went, the more the conversations got deeper and the more we got physically closer. To be fair, there was also lots of alcohol going on -but I did feel like his personality made me more attracted to him, physically. We ended-up kissing (a very good kiss, that turned into multiple) and were on my way to my apartment when Paul asked: “What do you think about Trump?”
I proceeded to state the obvious -I think he is a trash-bag- and Paul got a bit surprised. “I would vote for him”. I was shocked. Paul seemed like an intelligent guy. He had employees from different ethnics and was also living in a house with his two lesbian best-friends. How in the hell was he pro someone who was misogynist, racist and had rape accusations against him. I asked the question aloud and was met with a very bad answer: “I mean i didn’t knew all that. I would just vote for him because he is good with money”. In what fucking world, I asked. He is going to court because he never paid taxes. We were now in front of my apartment and my previous thirstiness had completely vanished. Paul had cockblocked himself, so close to the finish line. I said that I had a good night (which was not untrue for the first part) and asked Paul if he was okay to find back where he parked his car. He said he was and that he would text me back once he was home. Paul lived in Mirabel, which was about 45min away, and he was very drunk right now- so I just told him to not bothered -by the time he was able to drive back I would probably be asleep. He told me he was going to be back home within an hour - and to not worry because (and I cite) he “never got caught before”. Nice. Paul was a trump supporter and a drunk driver. I don’t see how you can come back from this. I went back inside, drunk but happy that I was able to catch these red flags before letting him in.
The next day, I wrote to Paul that this was not going to happen. I was sincere about the fact that his trump comments and his drunk-driving were a deal-breaker for me. I wish him the best and got prepared, somewhat against my will, for my next “first date” with the second contender.
For the sake of the story, let’s call him Javier. Javier was absolutely stunning. He looked like an underwear model, 6-pack included. He was from Venezuela, spoke french and a bit of english- but was more fluent in spanish. Javier was not someone I would have go for- based on what job he was doing- but he really insisted that we meet, so I finally agreed. He was a DJ. And don’t get me wrong, i have nothing against that- but I’m in my bed by 11 so if we are looking for long-term, I don’t think these two lifestyle will ever fit. I still agreed and we decided to meet in a coffee shop near Griffintown.
When Javier entered the coffee shop, my jaw literally dropped. Damn, was this guy hot. He dressed like an European model, no band t-shirts or teenager vibes. He looked like a successful grown-ass man. He hugged me hello -he smelled great and his accent was cute, too. So far, most of my senses were pleased, but I was a bit concerned that there would be a language barrier between-us, as I somewhat felt it by chat. To my surprise, Javier talked more fluently than he typed. The conversation was nice, but there was a few “red-flags” that confirmed to me Javier wouldn’t be a fit for a long-term partner. First- we didn’t had the same lifestyle at all. Javier future also seemed all over the place. He wanted to do his “cards” to flip houses, wanted to be a successful DJ, to buy a place and open his own bar, also wanted to store and sell car pieces from Venezuela- my head was spinning just hearing him talk about all those big projects- it didn’t feel like he had any clear steps planned for any of those.
Javier was also very emotional and fiery. After only an hour talking, he made it very clear that he wanted to feel that his partner was all about him. “I want my girlfriend to fight with me when I tell her I am going to do something without her”. I was a bit confused. “Isn’t that toxic? I mean wouldn’t you want that she trust you instead?” We had a long conversation about the fact that this behaviour (that i do find toxic) was in fact something that was important in his culture. Apparently the men want to have jealous girlfriends because they need to feel like they are important, and that's the way they want to be shown. That’s gonna be a no from me, dawg.
We were wrapping up our coffee date, now obvious for me that we weren’t a great fit, when Javier tried to kiss me. I declined politely, explaining to him that I wasn’t looking for meaningless hook-ups. The reality is that in another context, I might have agreed, but I felt a bit disgusting by the fact I was kissing someone else a few hours earlier. Javier was hot, but not enough to randomly kiss on an alcohol-free afternoon, when I just conclude we had no possible future together. I thank him for the coffee and walked back to my place with a mixture of deception and relief. I had tried to date. It didn’t work. Let’s try again next year. I deleted all my dating apps and went back to my life- happy to have been strong enough to not fall into any hot traps.
The relief was short-lived, as I woke-up with a text from Paul. He wanted to see me again and apologized. I was about to politely decline (he had nothing to apologize for - we were just not compatible) when he reminded me that I had left my favourite hoodie in the back of his truck (fuck). This hoodie was from my trip to Australia and I didn’t want to lose it- so I agreed to meet with Paul again. We would go for brunch the next weekend. Not long after, Javier texted me to ask for another date, too. I told him I didn’t think we were a good fit, but he persisted, and I began to question my initial judgment. Ultimately, I agreed. A week later, I was preparing for two second dates with the same two guys I had originally deemed incompatible, honouring my no-judgment self.
My brunch with Paul was nice, but it just confirmed that once totally sober, I had no attraction to him whatsoever. His personality was still lovely, but I couldn’t remove the drunk-driver trump supporter out of my mind. We had a nice conversation where he told me that he realized his algorithm only showed him pro-trump stuff- making him feel dumb for not taking time to better educate himself. I was both discourage by the fact google and social media’s algorithm were so fucked- and impressed by Paul for realizing and rectifying his belief. “I talked out of my hat. I feel very stupid.” I still felt like Paul WAS stupid for driving drunk, but all the other aspects of his personality were pretty cool- and I didn’t want to hold him accountable for just realizing that the news he consume were tailored to the views of people he was surrounding with. At least now, he knew. Unfortunately, in the end, the fact is that Paul didn’t attract me enough to be a lover or a fuck friend. I said goodbye to him, thinking to myself that I would write back a direct yet polite message later that day, to close the loop. Today, I am ashamed to say I forgot, and when I realized it was almost two weeks later- so I felt stupid and just didn’t wrote back. #ghostingOops
My second date with Javier was the next day, on a rooftop’s terasse. Once again, he arrived so well-dressed it felt like I was in a postcard from Italy. We sat at the bar and had a lot of fun, but my conversations left me with the same conclusion: I didn’t see myself in any type of relation/situation-ship with the guy. I thought to myself that if he tried to kiss me again, though, I might just go with the flow and bring him back home for a lil’ fun session.
We had just entered the elevator to go down, out of the bar, when Javier pushed me against the wall to kiss me savagely. I was turned-on for a fraction of second (I always find it incredibly hot when a man takes charge) but it turned into total disgust when I realized how bad Javier was kissing me. It felt like he wanted to eat my whole fucking head -i couldn’t breathe and everything around my mouth felt wet and gooey. When he finally pulled back, I had to wipe my whole fucking chin with the back of my hand.
“It’s very important to like how the other person kiss”, he said, smiling and flirting. Is he fucking serious? I was tetanized. We started walking back towards my house (his car was parked between it and the bar) and Javier stopped to kiss me again, and again, and again. Each one of those kiss more disgusting than the last. At some point, our teeth bumped, and I even felt a tongue near the entrance of my nose. I was trying hard to make him close his fucking mouth, make him follow my pace a bit more- but there was nothing to do. This guy was deaf to my body language. “You seem pensive”. I am not pensive, Javier, I am fighting for my fucking life. His hotness had completely vanished - I wanted this to be over. He insisted to drive me back home and kissed me one last time when we arrived. We were now more than 15 kisses in, and he still hadn’t adjust. I am all about passion but there is a way to do it without drowning your partner..
I managed to escape the vehicle and once in my elevator, I wrote to him immediately: “I had a fun date, but this isn’t going to work. I am sorry, I wish you the best.” At the same exact time I was hitting sent, Javier was sending a message asking if I wanted him to come inside. How in the actual fuck does he think I am turned on right now? I was not receptive to whatever he was trying to do with his mouth, turning more frigid every kisses he forced on me. I do not understand how he thought this was going well. After he had read my message, he wrote back, concerned: “Why are you saying that? What happened?” I didn’t felt comfortable telling the guy he had just cockblocked himself by kissing so badly- so I just replied “Nothing happened. I am just not feeling it.” He blocked me, a rush of relief going through my whole body. The next day, Javier wrote back asking if we could “just have fun”, undoubtedly clueless that this WAS what I wanted prior to those awful kisses. I politely declined, thinking this was going to be the end of my dating life for the year, but life threw me a curve ball that very next Saturday.
I entered my friend Alex’s flat and noticed him immediately. Tall, handsome, radiating positivity. His skin was between coffee and chocolate, his shoulder-length hair pulled back into a low man-bun. We started talking and the chemistry was instant- but he mentioned wanting kids quickly, when talking about his work. *insert deception horn. We continued to flirt here and there during the party, but I was pretty much set with the idea of letting that die with the night. When he left, later-on, he asked for my contact. I gave him, thinking that if he was reaching out, I might just accept and go with the flow. Once again, I think that I wasn’t against the idea of just fucking for fucking- as long as the person was interesting and a gentlemen about it.
The next Friday night, he reached out to me saying that his friend had cancelled on him and asking if I was free. I wasn’t loving that message -it felt somewhat like I was a plan B. I finally decline when he added that he would be available by 10. I was not that thirsty.
The next day, life piled-on even more on my plate by sending a package to my previous address. I had to go fetch it and while I was in the neighbourhood, decided to go chill at my favourite coffee shop in the area. After a few hours, I ended up with two numbers: one client that was sitting beside me at the same table and my favourite barista whom I fancied, back when I was a usual.
Ash (the name we will give my Barista, because he looks a bit like Ashton Kutcher) reached out to me a few days later to setup a date. I accepted. We met in the Canal lounge, the next Friday night. It took about 5 minutes for me to realize this was not gonna go anywhere. “Drugs” was his answer when I asked him about his passions.. I was about to assume he was a pothead but he continue talking about LSD and Mush and doing this on a very regular basis. Through the night, we had fun and laughed a lot- but did not find any points in common at all. We were about to hug goodbye when Ash bend-over (he was very tall) to kiss me. It was a good kiss and his hands grabbing my hips made me shiver a lil’ bit. “I hope we see each-other soon”, he said before walking away. Damn. Why am I not able to just have fun for a bit? I was already preparing the “breakup text” in my head, which I sent over to him the next week.
The following Thursday, I met up with my friend Mike for dinner. We settled at the bar and started chatting about our dating lives, which seemed to catch the attention of the staff, who eavesdropped throughout the night. By the end, we’d made friends with most of them, especially the tall, handsome bartender who really caught my eye. He was funny and jumped into our conversation, sharing insights and some juicy stories from his own dating life. He had studied psychology and mentioned that, while he enjoyed his work, he was a bit tired of fucking with people he considered shallow. “What are you guys doing after?”, he asked. By that point we had been flirting a little bit, so I told him I could go out with him, if he wanted. I was a bit tipsy and very down to just end-up the night with him. He wrote his number on my bill and I texted him, as I went out of the bar. By the time he wrote back, though, I had sober up and decided it was wiser to just fall asleep.
I texted him back the next morning: “Hey sorry, I sobered up and felt asleep. If you are tired of being a late-night call, let me know, i’d be down to go for a coffee or something.” He texted me back in the afternoon, asking if I was free the next day. I agreed to meet him in a coffee shop nearby, before his shift.
When I arrived to the coffee shop, he was already there. We sat and he ordered for both of us. We had an amazing conversation and were flirting a lot. He looked like he knew what he was doing, I am going to be honest. A proper fuckboy who knows what to say to get you in his web, and I wasn’t against the idea to dance with this danger. “I am working at 3, but i’d love to finish this conversation after”. We had met at 2, so I was a bit surprised of how quick this was ending. Another fuck-boy move. He was going to be out of work by midnight and it felt more and more like he was tying to invest the bare minimum to get me in his bed. “Yeah, I don’t think so. If you want a proper date, call me, but I am not going to meet you at midnight”. He seemed a bit surprised, but told me he was still gonna text me after work. He paid for the coffees and left.
I usually sleep at midnight, but that night I was going back and forth with the idea of just inviting him home. One minute past midnight. bling. “Hey, are you still up?”
The will power it takes to say no to a guy you find interesting and attractive, when you haven’t fuck in almost a year, lemme tell you. I took a deep breath and tried to think about what I truly wanted. Not having meaningless sex and falling for a fuckboy who clearly gave me signs he wasn’t in for anything more. I am trying to downgrade to a yellow flag - at most a burnt orange.. and this guy is giving me deep red ones. I know I find him a bit too interesting mentally to just fuck him once. This would be like jumping into something you know will hurt you in the end.
“Hey. I am up, but I was about to go bed. Out of self-respect, I will not go out with you tonight. Write back to me if you want a proper date. Good night, pretty boy.” He wrote back immediately: “I understand. I will write back to you soon. Good night xx.”
I looked at my phone for a second, a bit sad of letting go of that possible physical touch, but I knew deep down this was the right thing to do for me. I undressed, removed my makeup (until the last minute, I was ready to bring him home) and I felt asleep with a small hope that he would write me back and ask for a proper date.
The next night, Alex’s friend wrote back to me, inviting me to do something the same night -after his work. I was getting a bit bored of guys doing the bare fucking minimum. “Sorry, I’m not on call.”
He instantly realize that he had been a bit rude and apologized, saying that he was not trying to come across like he was doing a booty-call. He is just “like this”, more a “spontaneous” guy. If that isn’t the exact thing a fuckboy would say, I don't know what it. In the end, he did ask me out for the following week -trying to prove that he has genuine interest. I accepted, not because I believed him, but because I caught myself looking at if the barman had wrote me back (he didn’t). I knew if he did, I was going to be in trouble. My brain was spinning and reaching the only conclusion it could: how do fuckboys avoid catching feelings? They rotate multiple people at the same time.
I had the possibility to do the same, right now. I could rotate both of those fine man, have some well-deserved fun and split my attention enough to prevent myself from falling for one or the other. It seemed like a genius idea, which I entertained for a few days, until I realized that no- that was not who I wanted to be. Damn fucking mind trying to do the right thing, can a girl not just have fun for a second ?
In the end, I cancelled my dinner with Alex’s friend. My dreamy red-flag barman never reached out again, and I made peace with my decision of waiting to find the right person. I want to fall for someone, to get butterflies, to lose control. But if I can help it, I will make sure I don’t put myself in a situation where what I see and what I wish it could be don't align. And if it means choosing to be alone instead of having flings, then so be it.
Feral cat-lady it is.
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