I was 33, Kailey was 23. I was bartending and back at university, she was a pianist training to be a veterinarian. I was at the height of my confidence in the industry, Kailey was the most attractive colleague I’ve ever worked with.

Everyone has an ideal version of who they’d like to bang the most. Sorry if that’s crude, I’m just being honest. Call me sexist but how many women find every little physical flaw to reject men? Compare statistics on how men and women swipe on Tinder and I rest my case.

***

The first weekend I worked at the piano bar, the best job in my career, a young woman walked in. Besides loving beer and books I had a wandering eye for attractive women back then. She caught it instantly.

Kailey was the closest girl I’ve met who matched my ideal woman. Or more accurately, she was the closest one I made out with. She was tall (six feet), curvy, red headed, and decorated with tattoos. I’m not sure if she had any piercings because that would’ve made her an 11 out of 10.Kailey also had a stunning face and as she approached my bar I struggled to maintain my composure (and not drop my jaw).

Ten years into my career I was weary of dealing with the legions of fickle hot women in my industry. Most were waitresses and far too often the attraction wore off once they opened their mouths and shallowed how shallow they were. The average woman was nice enough but the proportion of flawed women (and men) is higher in the bar industry than most fields.

Kailey was different… mostly. Unlike most 23 year olds she had direction, hobbies and interests, a good head on her shoulders, and was down to earth (that last one is key). Besides being a master pianist she volunteered with animals, dominated at university, and was very educated. While I was 10 years older she was my intellectual match and in some ways surpassed my maturity (I drank too often back then).

Anyway, as Kailey neared the bar I fixed my posture, smiled, and looked her confidently in the eye. After all, when you bartend you control the booze and people need your approval to get drunk. I can’t remember who spoke first or what was said. I just remember trying to be as normal as possible and struggled not to check her out from head to toe.

Kailey ordered a 2 oz whiskey on the rocks and downed it instantly. That gave her points with me but with hindsight a 23 year old girl doing that as we met should’ve been a red flag. It was only when she took off her jacket, exposing her sexy red dress and figure, and sat at the piano that I knew she was a colleague. “JACK POT,” I thought to myself. This job was turning out to be very pleasant indeed.

***

Needless to say, seeing Kailey on the weekends was among the highlights working there. Over the next seven months we’d get increasingly flirty with each other. Eventually, I became more aggressive and went for her, despite our 10 year age gap. I have zero regrets!

She didn’t exactly discourage me. Kailey was playful: Commenting when I shaved, eyed me when she thought I wasn’t looking, and showed that alluring body language women use when they’re too young to know how to mask it. She even took an interest in my studies and interests, including my passion for military history. It’s something most people, women, and increasingly universities, find abhorrent.

It’s why many Canadians don’t know about Dieppe, Vimy Ridge, the Holocaust, or why supporting Ukraine against Putin makes sense. It’s also why most people in the West have half-baked and simplistic views on the Israeli-Palestinian conflict (the most complicated geopolitical issue of our time). Forgive my rant, I’m just a simple, washed up, former bartender.

Anyway, she once got drunk on whisky at my bartop and asked what my favourite wars were. That’s a weird question, even for me. But at the risk of sounding like a Prussian warmonger I listed conflicts like Hannibal’s war on Rome, the Napoleonic Wars, both World Wars and the Arab-Israelis Wars. Afterwards I thought my interest in the worst calamities of history may have turned Kailey off. Until the next weekend when she brought in a memoir of her great, great, great grandfather.

It was slow shift, or she was dressed provocatively, so I read the document thoroughly. Kailey was of German descent and the account was of a Prussian officer at Waterloo, who rallied to help the British beat off Napoleon’s last grasp at conquest. That was cool and I knew I’d secured her interest by then. Soon afterwards it was Halloween and she dressed from head to toe as Jessica Rabbit. It took all my willpower to not stare at her constantly from my bar.

After that I was confident and hungry enough to pursue her. But due to my habit of late night drinking and being burnt by many women the past few years, I tested the waters with friendly Facebook messages. Eight years later I’m sure I was cute and classy, unlike other times I’d been more foolish. Either way, her flirting and interest didn’t decline but nothing came of it for many months.

***

I should probably mention by now she had a boyfriend, but they had an open relationship (according to her at least). Word to the wise, never believe a woman who says this, it’s rarely true. That sounds like a rationalization for me and maybe it is. But I’ll tell you something cold and blunt: EVERY girl that I’ve dated, been with, or that showed interest in me the last decade always had a boyfriend, boyfriends, or girlfriends. Maybe it’s because I met most in the industry, the rise of Tinder and Social Media, or the general moral decay of society. 

Usually I didn’t find out about peoples’ partners until afterwards, though a few times I knew before. Judge me if you want, but to quote the bible, which I’ll never do again, “let he who is without sin cast the first stone.” Either way, I’ve never cheated on any woman myself, though I’ve come close, and no one cares when people with money and status do it, so I feel 0% bad.

Anyway, there was no breakthrough with Kailey until the bar closed its doors for good. Like many piano bars people loved it but only came in occasionally or when there was a performance. Apparently couples who sip half a wine bottle all night and rarely order anything else don’t realize their small checks don’t compensate for labour, rent, and food costs!

By then the restaurant industry in my city was already declining and having to dismantle my favourite bar was… beyond unpleasant. I didn’t cry but I comforted my colleagues who did. Had the bar been a battleship I would’ve gone down with it!

As the last day approached Kailey suggested, with considerable enthusiasm, that we grab drinks. Some words of wisdom for the ladies; most guys are impressed when a woman makes a move like that, it shows confidence and guts. “Finally,” I thought. Did I mention she was the closest girl I engaged with to have my ideal body type. She suggested a pub in the east part of town. It was an offshoot of my favourite bar and while it was an imperfect copy the service was good and it wasn’t rowdy. 

***

I wore my weathered but trusty leather jacket, best clothes, and was in an unusually upbeat mood. Then I got there early to assess the place and get a good spot, ideally where we’d have privacy away from leering, obnoxious men who infect bars.

But no battle plan survives contact with the enemy. Kailey came in excitedly, didn’t like the spot, and dragged me to the bartop. But that didn’t matter as she knew the bartender, we got free drinks, and it was a great time.

I can’t remember much of the date, mostly due to the passage of time and because it went better than most. If you’re a morose person like I was back then you remember the bad things more than the good. But I recall some cool and lame themes we talked about. 

She spoke of her mother, who told Kailey she’d go to hell if she didn’t denounce her atheism. Holidays with her must of been fun (sarcasm). I doubt we talked about my family because with a few exceptions they’re decent people. Somehow we got to beliefs and principles; a strange thing to bring up during a bar date. I can honestly say that’s never happened before, and its never happened again. Yet men are often interrogated over their status, job, and salaries on first dates, so I didn’t mind an exchange of ideas instead.

That told me something about Kailey. That she had a moral compass, decency, and didn’t just care about appearances and what other people thought. Those qualities age better and better over time. Out of all the women I’ve been with only a fraction of them had these things… perhaps I often chose poorly. Because too many girls I met back then had few passions besides TikTok, shopping, and cocaine. 

Whether I was drunk or just comfortable enough with her I shared my principles. From a messaging and sexy point of view they were lame. As a history nerd I spoke of liberal democracy, the quest for truth, and idealistic things cynical people scoff at. Unlike tequila, deep conversations like this don’t “make her clothes come off!” 

To Kailey’s credit she didn’t laugh or just pretend to listen. She listened softly and intently. Given what happened later it also didn’t alter the favourable trajectory of the date. Maybe she was tired of dealing with shallow and empty men and found me refreshing. Maybe Kailey was as well educated, cultured, and kind as I thought. Or maybe she was just 23, 8 oz of whiskey in, and found such idealism adorable. 

Eventually, she confided in me, either due her increased intoxication or she finally trusted me. She let her guard down and exposed her vulnerabilities. That’s something I rarely did until I got older because most women (those I met at least) took advantage of it. However, I always showed kindness to women and men who open themselves up because it’s hard to do, life can be hell, and it’s in my nature.

Kailey talked about the pressures of being a child prodigy, a first rate pianist, and typical personal and family issues. Being just 23 at the time and not figuring herself out yet was only part of this. It took me almost 40 years to do this myself and I sometimes wonder how older people are so harsh on younger generations. It can take a long time to find out who you are and what you want and the journey is full of speed bumps, crashes, tragedies, and regrets. 

***

Anyway, Kailey became more flirty and implied her standards weren’t high (which could’ve been another red flag). As she was a knockout and men have low standards I knew she had NO LACK of options for sex and relationships. Perhaps her insinuation was the final “come and get me” signal to slap me out of caution and just go for it.

For much of the date I had tested the waters by touching her leg softly whenever we laughed. But after this green light I rested my hand on her leg and caressed it gently. By the way, you should always be cautious about such things and pull away and apologize at the first sign of discomfort. Especially outside of an industry that’s dominated by alcohol, stress, and heightened emotions. But when Kailey turned towards me and leaned in to get closer I knew the night would end more pleasantly than I hoped.

However, I almost ruined my chances due to my twisted sense of humour. It’s a tragic flaw, I sometimes joke too much. Mostly because it’s better than succumbing to misery and humour is effective at alleviating tension and conflict, a key task of managing volatile bars. But context is key and sometimes things aren’t funny and just piss people off.

Somehow the discussion turned to cocaine. While I’ve struggled with booze and did weed for a few years, I never did hard drugs. I don’t judge people who’ve done cocaine or hard drugs, as much as I disapprove. We’re all flawed human beings, the industry is stressful and ruthless, and few people escape it without succumbing to “indulgences.” 

Anyway, I don’t know who brought it up, but I started making jokes about cocaine. Eight years later I remember Kailey’s reaction to my stupid jokes. With slight frustration she said “don’t you realize I do cocaine,” as if it were obvious. What followed was the longest silence of the night. It made sense given her many accomplishments, responsibilities, and the pressures put upon her. The stress placed on her shoulders, along with the fact many great artists succumb to “inspiration,” made white gold tempting. 

Given I’ve drank enough beer bottles to make a bridge across the English Channel I didn’t judge her. At the time I thought if Cocaine was good enough for the former mayor of Toronto it was good enough for her.

Otherwise, I remember being more embarrassed than disappointed, especially as 33-95% of my colleagues in 17 years of bartending probably snorted cocaine at least once. More selfishly, I worried I’d blown any chance of intimacy at the end of the night. I’m sure I uttered a quick apology and implied I really liked her anyway. 

Fortunately for me that “hiccup” didn’t matter because after last call Kailey offered to drive me home. That may not have been wise from a moral point of view since she had more double scotches than Max Payne. But I wanted her so bad! Did I mention she was the only girl with my ideal body type I managed a date with?

***

Anyway, on the way home I messaging her leg but I reached that point where booze catches up with you. There’s a reason you should have a three drink maximum rule on first dates. Not least because I can’t recall much afterwards. We got to my house, I gently caressed her hair, and she told me more about her insecurities. 

Finally, I leaned in to kiss her to initiate the climax of the evening. Instead, it would be its culmination; that point in military theory where armies reach their furthest advance and collapse. We had a brief, passionate make out session in her car. While it was very pleasant I often wonder how we tasted to each other. Between her 12-16 ounces of scotch and my 6-8 pints I’m unsure whose breath was worse. With hindsight I don’t care, it was great. Either way, I clumsily asked her afterwards if she wanted to come in, but she declined. 

Given how sloshed I was at this point I’m sure nothing would have happened so I gracefully accepted. The funniest part is before she left Kailey pointed to a house across the street. It was hers! My ideal women lived within 60 meters of me. Every time I walked by afterwards I managed a wide smile.

We rarely saw each other again. We had different classes at universities, different jobs, and the next time I laid eyes on her she was serving at a local bar. She blushed, lowered her eyes, asked the other girl to serve me, and kept her distance.

That’s the closest I came to having passion with a girl who had my ideal body type. But with hindsight the age gap, alcohol, and other issues get in the way.

That’s life.