That Time My Boss Convinced Himself The Perfect Girl Wasn’t The One

When we are so used to finding red flags, are we confusing go signals with those we should run away from?

Ellen "Jelly" McRae


The self-heartbreaker | Image created on Canva

My boss was the rare mid-thirties man in the tech start-up I used to work at. He was the only one in the entire office, no, building, who wasn’t married.

It wasn’t from a lack of trying, I might add. He dated; a self-confessed serial dater, in fact. And he was between women quicker than I could finish the bottle of vodka I kept hidden in the draw of my desk.

And I shared that thing around every Friday afternoon, too.

But my boss had this thing about the women he dated; he was very good at spotting the red flags. The girl he brought in who yelled at him for walking ahead of her on the exit stairs didn’t last long. And then there was the one who purchased her engagement ring after their fifth date. In hindsight, these red flags weren’t that hard to spot.

Then came the one. This girl had everything going for her, perfect for him, and the one he wanted to marry.

Everything about their relationship, from the outside, looked like his hunt for a wife would soon be over. And within a blink of the eye, he was single again.

What happened? I asked him. He said he found those all too familiar red flags. Yet, when he told me what he discovered, they didn’t seem like red flags to me. Or familiar, compared to the other girls.

Did my boss have it all right about this girl, or did he have his red flags upside down?

“Red flag” #1: When your friends don’t like your partner

The first “red flag” was the reaction of his friends, in particular one. His best mate’s wife.

She didn’t like the girl; they instantly clashed over a trivial remark about having children. The girlfriend said she wasn’t keen on having more than one child. And the best mate’s wife argued it was cruel to raise a child without siblings.

What should be an innocent debate turned into a fight, one completely ridiculous and metaphorical considering neither had any parenting…



Ellen "Jelly" McRae

I’m here to use my wins and losses in #relationships as your cautionary tale | Writes 1LD; Cautionary tale women's fiction |