First Date

After my separation, a friend had given me a small room in her house to land in for six weeks and I really did spend it wondering “now what the f*** do I do?”.

I’d done my grieving over the previous two years, so it wasn’t a case of wallowing in self-pity. There was possibly a degree of self-loathing layered with guilt. In any case, I wasn’t going out. I wasn’t meeting new people. I was in an emotional foetal position. And probably becoming quite boring.

During this time I discovered that some of my oldest and dearest friends had a wager about me. They had $20 riding on when I’d get off my backside and go on a date.

With clarity and resolve I decided to get this one off the table.The biggest problem I faced is that since I’d married young - 22 - I’d never actually been a part of the dating scene at any stage of my life. So I had NO idea what constituted a date, what you do on a date, what the expectations of a date actually was... I had no idea about how you find a woman to ask on a date. I had no idea how you ASK a woman on a date. I may have been 40 but I was the naive and terrified 18-year old man-child.

So..In a flash of brilliance I sent a text to a woman I’d met at an Engagement Party the weekend before. “Hey, it was nice to meet you at the party. Would you like to catch up for a drink this weekend?”.

This was safe right? Nothing could go wrong. Amazingly (to me!) she said yes. Nice. I was feeling good about myself. How hard can this dating thing actually be?

The day of THE DATE!!I arrived to the bar early. I was confident. I was upbeat. She walked in through the door, looking as gorgeous as I remembered her from the party. I went up to her and said “Hi!”.

She looked at me and said.. “Oh hi. It’s a small world isn’t it?”

WTF??

I was somewhat taken aback. I rationalised that it wasn’t a problem that I couldn’t recover from. Surely?“

Um... you’re here to meet ME for a drink..” I said.

She looked at me. Her eyes widened. “Oh” was all she said. There was a moment then in which time stood still.  Suddenly she sagged. Literally. Her shoulders slumped, her posture deflated, she dropped her head down and exhaled. Heavily.

She had absolutely no idea that I was the guy she had arranged to meet. Awkward.

Still, me being me, I persevered. I bought her a drink and we spent the next hour or so talking. She shared with me her story. She'd had a horrible breakup with her partner of three years and she was suffering through some serious medical issues. There were other things that I learned that I won't share here.

Returning to the small room in my friends house that evening, I realised that I’d actually achieved something. The worst date ever is something that allows a person to conquer their fear of rejection. It sets a REALLY low benchmark for the future and it won’t be that bad again.

I learned to take a risk and get myself out there.

And a good friend won herself $20.

cheers,

Simon.

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