The Cheeky Charmer questions: “Would this be a healthier way to date?”


I’m re-thinking my dating strategy. And yes, “strategy” is the correct word according to my (straight married) friends.

 “Dating’s a strategy,*” they say. “It’s a numbers game… Make a spread sheet”.

*How many times can you say “strategy” in one column? Four apparently 🤷‍♀️

Ok, they didn’t say “spread sheet”  but I did have a date with a woman who made one. I’m probably at the bottom in red 18 point Arial reading: “NO!”

It wasn’t a great date. I did my Donald Duck impression and she disappeared with my pub quiz winnings*. And no, doing a pub quiz on a first date is not sexy. Neither is my Donald Duck impression. Particularly when I do Donald having and orgasm. And yes, I just wrote that in a sentence….

“Doing a pub quiz on a first date is not sexy. Neither is my Donald Duck impression”

*To be fair I gifted her the winnings thinking there would be a second date – which was my first error.


My current dating “strategy” (that’s the fifth time now CC) involves meeting girls on random nights out, falling head over heels and hoping for the best.

How can you meet someone on a random night out and expect it to work? The odds must be a million to one. It’s just pheromones. PHEROMONES! The glue that pulls you in just long enough to bond, fall in love and then making it impossible to leave. It’s probably mother nature’s cunning strategy (number six) for building a family unit.

This is just theory of course. I don’t have a phd in chemistry. Just attraction 😉 I’ll stop now…🤦‍♀️

“Sooooooo, how will you avoid these pit falls Cheeky Charmer? What’s your “strategy”? (Lucky number seven) I hear you say.

My strategy (eight) is to revisit what I said in column one. Way back in October  I said, “I’m gonna try this modern dating thing” date multiple people before whittling it down to one lucky winner who gets to be my wife. 

Well I didn’t do that. Sure, I went on a handful of dates and got a decent amount of snogging in. But then I met Rose (see lesbian power move), fell hard and that was that. Until my heart was broken. Which was inevitable.

I didn’t date other people while we were dating. And that was a  mistake. Not because it would have changed the outcome but for my own sanity. It’s like a self protection band aid. 

“I didn’t date other people while we were dating. And that was a  mistake”

Continuing to dating other people, before locking things down, reminds you, you have options. We get locked into one person (and remember, it’s just chemicals) and lose sight of the possibility of anyone else. That’s why breaking up is so damn hard. They’re such a huge fixture in your world (possibly the biggest) that their loss is colossal. 

It’s only when you go out again and notice other women noticing you, that you realise you have options. What if we reminded ourselves of this at the beginning rather than the end? Would this be a healthier way to date? Not throwing all those proverbial eggs in one proverbial basket, hoping to make an omelette instead of a mess.

That’s where I am right now, back on the scene, noticing girls noticing me. I see my value, know my worth. I have options. What if I’d kept that awareness in the early days with Rose? Would I have stayed grounded before losing my heart?

Probably not! 🤣

But that’s where I am,  reaffirming my intentions from my first column, multiple date with multiple people, before declaring I’ve  found my wife. Maybe this way I can keep my dance card free enough that, if it’s not working with “x”, maybe it will with “y” or “z”. Or one of the other 26 letters in the alphabet…😉 and yes, I had to check how many letters there were…

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