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

39. Fly me to the Moon – Mr. High Flyer

39. Fly me to the Moon – Mr. High Flyer

Mr. High Flyer was a high flying accountant for one of the biggest firms in Sydney. I agreed to go on a blind date with him because my girlfriend told me:

“Oh he’s dreamy, loaded and all the PA’s love him… he’s super nice to boot!”

She had me at: “He’s dreamy…”

We decided to meet after work in the city.

My car had broken down, and I had to train it in.


You see, the Sydney railway system is the pits. I feel embarrassed when I see tourists using it.

I was running late so I called him:

“Heya, look I’m terribly sorry, my car broke down, so I had to catch the train and you know how Sydney trains are…”

He laughed, “Sydney trains are shit! Don’t worry take your time.”

When I finally arrived at the café, more than half an hour late, I was flustered and very apologetic: “I’m sorry I’m late again, thanks for waiting.”

He is cute, preppy, but cute!

He looked at me, smiled and then looked at my legs.

“Oh, I think you have a bit of dirt on your legs.”


I had dirty city bin juice, all down the back of my legs. I excused myself and sprinted to the bathroom faster than Cathy Freeman.

A few baby wipes later, new lippy and whitening eye drops, I was feeling 100% less sewer-rat-like and more of a lady.

“Thank you for that and I’m sorry again for being late.”

“Geez, enough with the sorries.”

He grabbed my shoulders and gave me a playful shake.

“OK, we good?”


“So I’ve heard so much about you: ambitious, smart, funny…”

“Hehehehe No, not really… I have to confess… I’m notorious for ripping off other comedians.”

“Don’t worry, everyone plagiarizes in that industry!”

While we were chatting, I noticed that Mr. High Flyer knew a lot about me.

Oh great, what did my girlfriend say about me, to get him to agree to this date?

“So enough about me, Mr. Private Investigator… what about you hmmm?”

It turns out, we were having coffee underneath his luxurious apartment block, he kept horses just outside of Sydney and he went to a pricey private school.

But, he was not arrogant about it.


When we finished our two cups of tea, I knew our date was coming to an end. He smiled at me and cheekily said:

“I’d invite you up to my apartment… but we haven’t even held hands yet.”

It made me smile all the way home…even if the train was overcrowded and it smelt like death, I smiled.

Have you ever experienced a wardrobe malfunction on a date?

Where you able to turn things around? What do you think?

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