Kaitlyn sat next to me on the couch in the basement. She turned her body towards me and smiled shyly. Kaitlyn stroked her long, black hair and stared at me with her dark, gorgeous eyes. She laughed at my joke, leaned in, and waited for me to make a move.

***

I was working at a decent chain restaurant back then. It was dark, modern, and staffed by hot, young women. But I hadn’t wanted the job as I was in my last year of university and was tired of the bar industry. Unfortunately, my roommate needed an experienced bartender for weekend nights and since I owed him many favours I caved and joined the team. 

The job was mostly boring. The bartop got few customers, I couldn’t take tables, and after 10pm the last hours of the shift went by slowly. Tips were also mediocre and it soon became apparent why it had been hard to fill the position. But given my predecessor was fired during the MeToo era for peeping into women’s washrooms it was clear they needed employees of a… better caliber.

Naturally, the consolation prize was my cute colleagues. There was a curvy red head my girlfriend flirted with in front of me. There was an adorable, skinny blond who was friendly but soon quit to run an OnlyFans account. There was a flirtatious, knockout black haired girl who ended up being the daughter of a milf I’d hit on at a previous bar. Needless to say, it was awkward when I dropped off drinks for them the night they came in together.

There was a small, loud Asian girl who was so excitable she could have taken four Red Bulls each night. She was 10 years younger than me, promiscuous, but too much of an SJW. But despite being the only person to accuse me of white privilege she always invited me to her place for drinks… no matter how many times I mentioned my girlfriend!

Then there was Kaitlyn.

***

Kaitlyn was the first employee I met when I walked through the door for my initial shift. Despite my usual aloof demeanour she gave a real smile instantly. She was kind, easygoing, and warm. I was attracted instantly, but I wouldn’t say I was smitten. After giving her a reasonable greeting I asked if my roommate was working and dived into my first shift. 

The staff were pleasant from the beginning but given I was significantly older I didn’t socialize with many of them often. Kaitlyn was different, probably because she was more easygoing, friendlier, and soon found me attractive. But I didn’t know that at the time as I had a girlfriend and didn’t see the obvious signs.

I remember the first time I really noticed her body. It was my second shift and my mom was dropping me off at work (thanks to my DUI). Kaitlyn was setting up the patio. Our dress code for the waitresses wasn’t exactly subtle and she was wearing a short skirt and a loose black shirt that showed off her figure. Catherine was of average height, slender, and had the body type of a dancer. 

As I subtly ogled her body my mom asked me if such ‘provocative’ uniforms were typical of the industry. After confirming that was the case my mother said “that’s terrible” in a slightly outraged voice. Being a typical male I rolled my eyes and asked her if she had not seen the various places I’d worked at over the years. 

Needless to say, I was friendlier with Kaitlyn after that moment. However, mindful of my girlfriend, I kept telling myself “you can look but you can’t touch.” But she would start coming in for drinks off-shift and became increasingly flirtatious. Unfortunately, she would bring her friend, Bailey. Bailey was the exact opposite of Kaitlyn. She was overweight, ugly, edgy, and a bit of a bitch. 

The staff apparently felt the same as they would cut her down behind her back. I was once asked what I thought of Bailey and was about to offer up an earful. Instead, I merely said “you know when we were young and our parents said if you have nothing nice to say about anyone you shouldn’t say anything at all… well that’s all I got.”

***

At the time I was 36 and Kaitlyn was 22, but she was more than a cute, young body. She was extremely intelligent, knew four languages, and was sweet and authentic. This was surprising given her mom was ill and her father was a mean, raging alcoholic. Then again, maybe that’s why she liked me given she likely sensed I was a surly drunk, masked by a generally kind demeanour.

I knew Kaitlyn liked me when she kept flagging me down on a slow Friday night. She was there with her annoying friend and they were both beyond tipsy. As it was dead I “found” time to chat and tried ignoring her friend. But I was fortunate one of the managers, Julio, who would sleep with anything, was trying to get with Bailey that night. Julio was always nice to me and was a fun guy, but he inevitably thought with his dick. During the Covid pandemic he’d even let girls come in after shift and dance on the bartop… which nearly got us fined and closed!

Anyway, Kaitlyn was surprised I was 36, having assumed I was in my mid-twenties. Indeed, I was in great shape at the time and women often underestimated my age. Which was certainly better than the times I was fat with a drunken, bloated face. At such points they guessed my real age with more accuracy.

After some increasingly friendly small talk Kaitlyn asked if I was having drinks after my shift… obviously wanting me to join them. I knew I shouldn’t have given my girlfriend but I again remembered “I could look but not touch.” That and the cheap staff drinks and my blatant alcoholism made the outcome inevitable. “I’m not sure… depends on my tips,” I said lamely. She initially looked disappointed but doubled down with an eager look and smile.

I soon walked away to ask my supervisor, who happened to be my roommate, if I could get off early. He saw through the act instantly. My roommate knew my penchant for younger women and drinking, and was mindful of my girlfriend. But it was dead and he wanted to save labour so he agreed. Yet before I got off he said “don’t do anything stupid” in an ominous tone he used often with me throughout the years. I would seldom listen.

***

Kaitlyn and I would only drink together a few times but the sexual tension was obvious. Unfortunately, we got too drunk and combined with the passage of times means the details are hazy. While Julio distracted Bailey I used what I call defensive flirting with Kaitlyn. I smiled a lot, told  jokes, used subtle body language, and offered small compliments when she talked about school and her life. 

She was proficient at linguistics, knowing German, French, and Italian. But her real passion was journalism, which she was taking at university. I don’t trust journalists, although I respect the field and realize free media is necessary for democracy. But maybe it’s because my parents were unfairly slandered by a journalist, my education in public relations, or just the sad state of the media landscape, but I’m always weary of journalism.

Frankly, I was surprised Kaitlyn was in journalism given she was extremely honest, kind hearted, and far from ruthless. Maybe she was like me, who always sought the truth, but unlike myself she was still idealistic and hopeful about humankind. However, her professors had challenged many of her views and work and Kaitlyn was having a crisis of confidence. 

Given I’ve had many family members and people attack my confidence and self-esteem over the years, for no reason other than to bully or cover for their insecurities, I reassured Kaitlyn. People were messy, complicated, and often contradictory creatures, I told her. Then I said a few opinions, even from supposedly well renown professors, isn’t the final judgement on anything. Too often high status critics are left behind in the grand scheme of things, while the objects of their slander live on in history. People remember the Socrates and Churchills… not their detractors.

Otherwise, our conversation that night was more light-hearted, especially once the booze took hold of us. I was about 6 feet, 170 pounds but she kept pace with me… thanks to drinking earlier and having wine. Eventually she got very interested and flirty, sitting on the edge of her chair, smiling widely, and almost giving me bedroom eyes. But as much as I tried to engage in innocent flirting my interest slipped through and I called her “babe” the way I address my girlfriend. “WHOOPS, I immediately thought, and tried reigning myself in.

But Kaitlyn was fine with this and escalated by getting closer. Finally, remembering my girlfriend I enacted my exit strategy, pretending to get a call from her. I wished the group well, said goodbye to my roommate, who shook his head at me, and went home. As I passed out on the couch I promised myself I wouldn’t have drinks with Kaitlyn again.

***

So obviously, next time she came in with her friend I had drinks with her again. But to be fair, she was dressed hot and asked me to. I didn’t want to be rude after all…

I don’t remember much of the evening, as usual, thanks to how much we drank. But I recall consuming a healthy portion of staff drinks and being disgusted by Julio’s increasingly aggressive attempts to get with Bailey. It’s guys like that, who sleep with anything, that gives even the most ugly girls (on the inside and out) the illusion they’re out of most guys’ leagues. Sorry if I sound bitter, it was hard for me to usually get a date even when I was confident and in top physical shape. Then again… I have standards.

Anyway, Kaitlyn was as flirty and comfortable as usual and I tried ignoring Julio and Baileys’ unseemly displays of affection. Eventually, Kaitlyn asked if we wanted to go to another bar, which happened to be near my home. I probably should have said no, given I was already liquored up and because of my girlfriend. It was too bad my roommate wasn’t there, he would have intervened and told me to quit fucking around.

Unfortunately, alcohol has a tendency to corrupt inhibitions and especially judgement, and subconsciously I wanted to get Kaitlyn home with me. So we went to the other bar, had far too many shooters and drinks, and started to slow down. The bar was nice enough, but the service was slow… as it usually was. I had no idea I’d end up working there, and it would be my last industry job. But that’s another story.

As last call approached I wanted to invite Kaitlyn back to my place a few blocks away. By now alcohol had drowned my consciousness and I temporarily forgot about my girlfriend. But I needed a few moments to sober up and wasn’t sure how to broach the subject. It’s not exactly straightforward asking a 22 year old to come home with you when you’re in your mid-30s, especially when her friends are at the table!

Fortunately, one of them asked if there was anywhere else to go and I suggested my place. This was deemed acceptable and we arrived there a few minutes later.

***

I didn’t have as many girls over to my old place as you might think, given my industry and many dates. Usually, I’d prefer we went somewhere else since I’m a history nerd and I’ll just say it, most industry girls are more shallow than a puddle after a rainstorm. Btw, if you don’t like that joke it was created by AI!

However, Kaitlyn was different, as she was educated, cultured, and intelligent. Unlike most girls, who noted my lack of expensive trinkets, Kaitlyn was impressed with my 100s of books, busts of historical figures, and maps of the world. 

But we weren’t there to study. While my goal was simply to make out with her, given I had drank too much to “perform,” there was an obstacle… or two. Bailey and Julio were also there and the three of them were on the couch opposite of mine. I was unsure how to get rid of those two… especially given my roommate was sleeping upstairs. 

Most likely we just made small talk and I hoped Bailey and Julio would soon leave together. However, I was wrong with Bailey wanting to stick around to prevent me from “advancing” on Kaitlyn. To be fair, as much as I didn’t like Kaitlyn’s friend she was naturally worried about her, not least because of our age difference, but that didn’t change my annoyance.

Eventually, Kaitlyn broke the impasse, or tried to at least. She sat next to me on my couch. She turned her body towards me and smiled shyly. Kaitlyn stroked her long, dark hair and stared at me with her dark, gorgeous eyes. She laughed at my joke, leaned in, and waited for me to make a move.  This was it, now or never, sink or swim, D-Day, etc. 

I did nothing…

Maybe it was because her friends were still there, or the booze was finally catching up to me. Maybe I belated remembered my girlfriend and how guilty I’d feel even If I just made out with Kaitlyn. Or maybe I just chickened out and didn’t rise to the occasion. 

Instead I closed off my body to her, steered the conversation towards something boring, and Kaitlyn sensed my retreat. She returned to the other couch with her friends, and the night soon ended… with them all going home.

***

The next day Kaitlyn texted me that she had forgot something at my place. Sure enough I found it on the couch and she asked to come get it. At this point I wasn’t sure if I wanted to hang out with her again… realizing that I had developed a small infatuation for Kaitlyn. I decided I’d play it cool when she arrived.

She came over, I got her stuff, and we had a brief conversation near the door. It was friendly, normal, and not awkward. But it wasn’t flirty or ladened with any expectations. Remembering how I nearly cheated on my girlfriend the previous night, I quickly told her I had to get ready for work and would see her another time. 

We never hung out again and this was for the best. We wouldn’t have become a couple given our age difference and getting with a woman 14 years younger than me wouldn’t be worth the guilt I’d have to hide from my girlfriend.

But as usual, being a history nerd I sometimes wonder “what if.”