You’ll have seen the recent post from our friend Dan Bacon over on The Modern Man – and for any of our male readers, you might want to check out his top-drawer advice on all things love, sex, relationships and approaching women – about women wearing headphones. Sure, this has its uses, and it’s been extremely well received by womankind the world over, but frankly, as a man, that’ll be the least of your troubles.

What about all of the other common face and headwear that women regularly sport? We’re talking glasses, contacts, lipstick, mascara, face paint, head bands, bandanas, fascinators and – worst of all – hats. There’s a reason spies wear hats. They change everything. An absolute minefield. So how do you talk to a woman wearing a hat?

It’s not easy. It will depend on the type of hat in each instance. Here, we explore the ins and outs of human interaction with a woman in varying types of headwear. You’re welcome.

1. The cap

cap — Throw enough balls at her and one of them will stick.

A white cap such as the one in the photo above implies that this woman loves tennis. When you spot the cap (and the woman attached to it) heading towards you, it’s time to pull out all the stops – and the props. Grab a tennis ball from your bag o’ tricks and hurl it towards her. If she catches it, great – you’re in there. If it hits her hard and she screams out, but then looks up at you and smiles, you’re safe. If it hits her hard and she screams out, and begins to cry, run angrily towards you, or perhaps away from you in fear, better luck next time. As any tennis player will know very well, you actually cannot win them all.

2. The beanie

A woman in a beanie? That’s clearly a cold woman. Play the dominant man card and approach her with your arms wide. When she looks up at you, suggest very quietly that you could be her human cocoon – a large chunk of man to keep her warm through these cold winter nights. We’d expect her to snuggle in right away, desperately grateful, but, if she continues to resist, lower your arms and begin to edge backwards. If you’re genuinely worried about her temperature, you could leave your coat behind for her.

3. The top hat

A woman in a top hat – any man’s worst nightmare! But don’t panic. Chances are this woman belongs to a circus, so you’ve got to know how to get her attention. If the situation lends itself to it, consider entering on a trapeze and literally sweeping her off her feet – and don’t ask her first. It’ll give her enough time to say no. If there are no available trapeze opportunities, simply sporting a sequinned cloak should do the trick. Run up to her, whizz your cloak quickly around her head, write your number in Tipp-Ex onto her top hat and run off again. Genius.

4. The cowboy

You don’t have to be an expert on women to know that any woman wearing a cowboy hat is a bit slutty. It won’t take more than a casual ‘Howdy!’ and a wink for her to fall into a giggling heap and invite you back to hers. Let’s think about how that conversation is likely to go in advance.

You: Howdy! *wink*

Her: Hahahahahahahahahahaha! Do you want to come to my house?

You: Yes please.

5. The witch hat

Based on experience, we’d steer clear of any woman wearing witch hats or anything that would imply that they are linked to the occult. Nothing good comes from it, and you could find yourself waking up with a few extra fingers than you went to sleep with, if you know what we mean. Do you know what we mean?

Do you?

Bonnie Pumphouse

Bonnie began her professional life selling caravan kitchens. She then took on a part-time role throwing lady parties for a well-known sex toy retailer, but they parted ways over artistic differences. She now splits her time between a much higher end sex toy retailer and writing exciting, inspirational articles for Glamourless – all aimed at REAL women like her.