Four Ways That Flirting at Work is Like Jaywalking

You have to ask yourself: is it worth the risk?

Gray Miller
5 min readJul 16, 2022


Photo by [][Volodymyr Hryshchenko] on [][Unsplash]
Photo by Volodymyr Hryshchenko on Unsplash

Do you believe workplace romance is a good idea?

According to (via 38% of the working population actively agree with you. Some surveys estimate estimate that more than one out of every five marriages start as an office romance. Some of the highest profile couples — Bill and Melinda, Barack and Michelle, Abelard and Heloise — met at work.

My partner and I sort of met at work — she was in a class I was teaching (and yes, there are all kinds of problems of power and ethics involved in that). In truth, almost every other significant relationship I’ve had has been someone I met in a “work” environment.

And yet I’m going to tell you right now: workplace romances are a bad idea. It’s a lesson learned in the #MeToo era: if you have an office flirtation that didn’t end up in a lawsuit or worse, it’s not because you did it right.

It’s because you were lucky.

Jaywalking is the perfect allegory for flirting at work.

Four things have to happen in order for you to successfully cross the street outside of a crosswalk:

  1. You have to be aware of cars around you.
  2. Likewise, cars have to be aware of you.
  3. Nothing can change on the street for as long as it takes you to cross the street.
  4. If there are laws against jaywalking, you’d better hope they’re not enforced — or you need to not get caught.

Similarly, if you’re going to be flirting with your coworker, all the following things have to go right:

  1. You have to be aware of whether your coworker is interested in you. Guys, especially: you are really bad at knowing whether someone is interested in you.
  2. Your coworker has to be aware of your emotions — starting with your interest in them. How do they become aware? Usually because you flirt with them — and the line between harmless flirting and sexual harassment is usually about three steps behind you.
  3. No unexpected changes — professional or emotional — for as long as the



Gray Miller

Gray is a former Marine dancer grandpa visualist who writes to help adults figure out what they want to be when they grow up.