Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

7. Jail House Rock! Mr. Jail Bird

Mr. Jailbird is a friend of my older sister. He asked my sister if he could get my number to ask me out. Under normal circumstances I would object to this.

But of course, there is nothing ‘normal’ about my 3six5dates quota, so I told her that it would be much appreciated.

We met at an ice cream parlour, since I love ice-cream, and if he turns out to be a ‘no-go’, then I can finish my ice-cream in record time.

As I arrived, I looked for a guy with tattoos (my sister mentioned he was inked), and I spot him straight away.

He is sitting at a table by himself, surrounded by other tables of parents and kids. He has a single red rose for me.  As we give each other the regular cheek-to-cheek kiss and he hands me the rose.

Is that the fluttering of all the female hearts in the ice-cream parlour?

My face goes bright red but I can not help but smile.

He is absolutely gorgeous…

…tattoos up to his neck, cropped hair, grey muscle top, slim-fitting jeans and havaianas.

Note to self: must be nicer to my older sister. 

“So what ice-cream would you like?”

“Surprise me.”

He brings back two macadamia and caramels in cups.

Sweet Jesus, I think I just sold my soul.

“I hope you didn’t mind me asking for your number. You just looked really cute in your sister’s photos and I thought we could be friends.”

“Of course I don’t mind, I’m always up for making new friends.”

Our conversation flows effortlessly. I feel like I’ve known him for years… until he drops a bomb.
“I’m not sure if your sister told you, but I’ve been in jail before.”

My heart stops and he obviously sees a shift in body language because he puts his hand on my hand and tells me that is was not for anything serious. I try my best to show him it does not bother me.

Well it was serious enough to land you in bloody jail!

Note to self:  if I ever date him seriously, do not tell mum about this… ever.

Our date ended because we both had to run, but I found myself wishing we could stay a bit longer.

He is definitely getting my attention. 

I think it is because he is a gentleman, with a scruffy bad-boy look.

Definitely going to ask him out soon.

As soon as I get into my car, I call my sister.

“Did you know he’s been in lock up?”

 What do you think? Does it make any real difference as to whether you wanted to see them again?

Have you dated someone that was locked up? If so, were they in jail for anything serious?




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