The people you should never hit on

A super awkward encounter over drinks drove home a very important rule that Jana Hocking wants to share.

Jana Hocking says there are hard and fast rules about who you absolutely cannot hit on.

Oh the heart is a funny beast. It can lead us into all sorts of trouble. In fact, mine seems to enjoy beating twice as fast for all the wrong types of people. Why you gotta do me wrong heart? Why!

But last week, during a late-night scroll through Instagram, I stumbled upon a gem of a quote from a popular lawyer on Instagram.

His words, though amusingly blunt, struck a chord: “Today is NOT the day for a 48-year-old restaurant manager to confess his love to the 20-year-old waitress in a long, cringey text. But it’s gonna happen. It happens every year.”

The Instagram post. Picture: @attorneyryan

Jana Hocking.

This cheeky observation reminded me how often people misread the signs of attraction and interest.

Reflecting on this, my mind wandered back to a recent encounter where I found myself in a similar scenario.

It was with a businessman who asked to meet for a drink to discuss me potentially becoming an ambassador for one of his products. It was an “adult” product (ok, ok it was for a vibrator) so the conversation was never going to be PG-rated but I didn’t expect it to be so well… misguided.

I met him at a popular restaurant, and he asked what I would like to drink. I said a glass of Pinot Noir, and instead of one glass he ordered a bottle.

Ok I thought, this is fine, I guess we will be here for a while. But then he kept topping up my glass after every couple of sips.

Hmm…

I decided to take it slow because this business chat was important to me, and I wanted to keep a clear mind. He, however, did not. He continued to down that bottle and order another one whilst attempting to flirt with me.

Infuriating.

Professional drinks are not an opportunity to hit on somebody.

I soon realized that he didn’t actually want to have a business meeting, but an afternoon on the plonk with a woman who occasionally writes about sex for a living.

Why do men consistently think that just because I write about sex, I will want to have it with them. Specifically. Drives me bonkers.

Anyway, it turns out these kinds of scenarios aren’t that uncommon. It’s a universal awkwardness—one where someone completely misjudges their shot at romance (or a quick shag).

So, in the spirit of “Not today Satan!” here is my list of people you should NEVER pursue…

The “Banned” List:

1. Anyone who ranks below you at work (yes bosses, I’m talking to you!):

Mixing work and romance can lead to HR nightmares faster than you can say “I just thought she was really into me.” So bosses, don’t be chatting up the hot secretary. Yes she’s got legs that could reach the sky, but you’re putting her in a really awkward position. (Not to mention that you are being completely unprofessional.)

If she rejects you, she’ll worry her job could suddenly be made redundant – we’ve seen this happen before people! Or if she does hook up with you, she looks like she’s just trying to get ahead. There’s a power imbalance and relationships should be built from an equal platform.

2. Your Best Friend’s Ex:

To be fair, not all of them. Just the ones they were serious with, and perhaps left someone broken hearted. There are plenty of fish in the sea, you don’t need that one particular mackerel. Respect the friendship boundaries unless you’re aiming to star in your own personal drama series.

Jana Hocking points out the no-go areas.

3. Anyone Significantly Younger than you:

As the Instagram lawyer wisely pointed out, age gaps can sometimes mean vastly different life stages and interests. We don’t need to be fighting off the advances of men who are old enough to be our father’s. Ick.

4. Your Neighbour:

Sure, everyone likes to borrow a “cup of sugar” every now and again, but close proximity can make things incredibly uncomfortable if it doesn’t work out. You don’t want to be applying lip gloss every time you take the bins out, so they don’t catch you looking gross post-breakup.

5. Your Therapist/Counselor:

As someone who loves a good therapy session, I can understand how these wise, caring people who calm your nervous system all of a sudden they seem like knights in shining armour. But for the sake of maintaining a professional relationship and your own mental health journey, this is a firm “no-go” zone.

Let them teach you how to fall for emotionally available people instead. That’s what you’re paying them right! Or is that just me?

Navigating the seas of romance can be perilous, but armed with these insights, hopefully, you’ll dodge a few more of those cringey confessions and awkward encounters. Remember, timing and mutual interest are everything in matters of the heart — don’t be the 48-year-old sending a cringey text to a 20-year-old waitress.

Jana Hocking is a columnist and collector of kind-of-boyfriends | @jana_hocking

Originally published as The people you should never hit on