Despite what many guys think, you aren’t automatically mobbed by hot women once you become a bartender. That wasn’t my case at least. Maybe I usually didn’t work at the coolest places. Maybe it was because outside of the acting I put on for customers, I can be quiet. Much of it was probably because I was overweight half of the time and drank too much 90% of the time. Finally, unlike 95% of men, I didn’t just screw any female that showed me interest. Most guys who say they’re players tend to slay more dragons than rescue princesses. When your standards are rock bottom any man can be a stud!

There are other reasons most bartenders don’t swim among mermaids. They compete with other bartenders and waiters, and legions of hungry men who infest bars with their sinister presence. And, for closing bartenders at least, you’re there until 3 a.m., mopping floors and turning off the lights. By then most girls have gone home, or went home with someone else!

I’m not saying I never took home colleagues or customers, but I’d never brag about my statistics… especially over a 17 year long career. Certainly, I didn’t live the life of a popular night club DJ, who can pick from a predictable supply of young, shallow bar girls each weekend.

***

Anyway, during my time at the piano bar they hired a strikingly beautiful blond woman. Let’s call her Sally. She was in her early 30s, close to my age, but could easily have passed as 25. Besides some initial conflict between us, common in the industry, we formed a bond.

We quickly became very comfortable and friendly with each other. This had not been common for me during the last 2 years at my last toxic job: Much of the toxicity had rubbed off on me, and even today I don’t like who I was during that period.However, now I was going back to school and this bar was turning about to be great, so I was becoming more sociable and relaxed.

It had been a long time since I had a girlfriend or even found a date. But while I was very attracted to Sally and we went to some bars together, I’d never made a move on her. This was partly because she had an on-and-off relationship with her dirt bag boyfriend… the kind that mentally abuse and cheats on women. She also had 3 kids and I’ll just say it… I don’t like dating single mothers. Call me Hitler if you want but given the ridiculous checklists some women (who usually die alone) have for selecting men, I don’t feel bad.

But more than anything else, I wasn’t sure if she was into me, or was just being friendly. My instinct, and perhaps ego suggests she was, but in the past I misread women so I was being cautious. That and so many women in the industry are blatant teases who CRAVE attention. They suck every oz. of attention from naive, decent guys, without hesitation and remorse, while banging numerous guys on the side. When you’ve been burned enough times even the most obvious signs can be missed or dismissed because you’ve become jaded and don’t want to be used.

Yet despite all of this, I liked Sally, we were getting closer, and I hadn’t put her into the “you’re just like most other people I’ve dealt with” pile. The one where all of us have thrown so many disappointing men and women who tell us what we want to hear, lead us on, then let us down.

***

Anyway, her intentions became obvious during a weekday shift at the bar. It was completely dead, with only my friend Leon the line cook drinking at the bartop. I alternated between talking to Leon and Sally until I cut her early to go home.

Before she left our conversation took an… interesting turn. I can’t remember exactly how it went but as a historian I recall the main themes.

She told me which days her kids spent with their deadbeat father. I’m sure I was like “oh.” Then Sally mentioned she liked drinking wine at home often. I thought “cool.” Then and I don’t know how she said the following in such a casual manner: “I like to take long baths.” By now I was extremely enthusiastic. Finally, she told me I should come over to her place soon and gave me her address. 

I’m 100.1% sure I agreed but we didn’t set a date (a fatal error). I do know that while I was excited I remained relaxed, easygoing, and not aggressive. Again, I’d learned to play it more cool after previous screw ups. Then she went home and I returned to the bartop to talk to Leon.

He heard the whole conversation and being a good friend hadn’t interrupted it, as some jackasses do. I’m sure he had a shit-eating grin and I merely said, in a classic understatements: “I’m beginning to think she likes me.” I can’t remember much from Leon’s conversation (excited at the prospect of drinking wine and having sex with a blond bombshell in her bathtub). However, cynical as always, I asked Leon if he thought she was being legit or just leading me on.

Leon was a great friend, had been in the industry longer than myself, and always told the truth. He told me she was being real so needless to say the rest of the shift was more enjoyable than usual.

You probably think the best part of the story is yet to come. A tale of wine, passion, sex, possibly even romance. But there would be no Hollywood scene, or even a fun, drunken screw.

Instead, she was fired the next day, or soon after, and it would be weeks before we met in person again. By then whatever spark was gone, or she had gone back to her idiot ex, and I missed my window of opportunity. We would hang out a few more times, and message occasionally, but I never did enjoy wine and sex in her bathroom.

As a student of history I always say the what ifs never matter as much as the what dids. But I also know the what ifs tend to be more intriguing. Because that what if would have been far more amazing for me, and interesting for you, than the what did happen.

Life’s not fair!