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A date in the life of JD - PART 1 (of many...)

I am not proud to say I am twice divorced, but I am, and as they say any crash landing you can walk away from is a good one. 




The first marriage was for 20 years, the second, barely 20 months.  My circumstances are like most in my age group: the physical connection stopped with wife number one, and with wife number two, it was porn star sex, morning, noon and night. I thought my prayers had been answered, only she was missing a brain and was trying to convert me to a religious cult. As the dust settled, I found myself with yet another separation hangover. I was broke and lying on a blow-up bed (yes, really!) but, hey, at least it wasn’t a blow-up dolly! 

So how does a six-foot-tall, fit, professional fifty ‘something’ year old successful lawyer in Sydney’s eastern suburbs get so unlucky in love?

Let’s backtrack a bit: a lot had changed in the dating game when I found myself back on the market. I was keen to meet the woman of my dreams and I was prepared to do whatever it took to find her. I bravely took to RSVP - the premier platform for online love.  It took me 17 attempts to draft a profile and I was too nervous to add a photo.  Imagine the flack I would get at the next partners’ lunch if they saw me on such a site? 

I graduated from RSVP with honours and was admitted to a master’s degree in Tinder-ology, earning multiple frequent flyer points and finally making it to the Chairman’s lounge of dating.  I was spending a fortune on “kiss dollars”, and hoping that the kisses would be returned in kind, without any unwanted extras (like herpes).

I soon learned that everybody on Tinder has at least 10 on the go at any one time. I made it my life’s mission to understand the ‘system’. 

I dated the A-Z of women, (or at least the A to X) from alcoholics and anorexics to hobbits and xenophobes. My postgraduate studies included the luscious, Botoxed and lipo’ed ladies of the Eastern Suburbs with their Teflon coated nostrils, their designer handbags and eight-inch Christian Louboutins. We’re talking more fillers than the Selleys bar at Bunnings and more Botox than Kim Kardashian. Tinder alert, incoming! Air traffic control to Claire; you are clear to make your final approach, Sue and Jennifer maintain holding patterns please.  Veronica, running low on fuel, requests an emergency landing.  All hookers and trannies divert to Melbourne. 

Thank you for swiping right. Standard flirtatious and totally original opening line in the DM, “Hey how’s your day been??”... and the barriers open, the horses are racing, and we’re sprinting down the straight in the 1200m “Love Handicap”.  

So what did my first month of internet dating look like?

Here are three early memorable experiences that many may think is the norm, but for me, I was left dumbfounded. Was this really what single life was all about?

I do love a blind date on Melbourne Cup Day, and the fillies were out in full force at Sydney’s Double Bay where I was about to meet a sultry blonde rocking her racing day best. It was a last-minute swipe right and I checked her out on facebook and was off and running down to a notorious watering hole in Double Bay, Mrs Sippy. The trout pouts were on parade and the champers was flowing and my date greeted me with a lucious kiss and “come on babe, let’s get a drink.” This girl could put away more booze than the delivery truck at Dan Murphy’s. She was sexy in a skanky way. I was completely sober when I arrived and had a couple of glasses of bubbles to catch up.


It shocked me at how loud, crude and rude the whole atmosphere was and it was so damn noisy that we decided to go to the InterContinental. Barely able to walk, when we arrived she suggested a “gin and tonic” to clear her head. I thought to myself, praise the lord and pass the Beroccas. Meeting a woman who is already paralytic, is not my idea on how to get to know her; so benefit of the doubt, I invited her out again. We had two more dates in fact, all equally booze filled. But the shock was actually when she sent me a photo of her teenage daughter wearing lingerie I realised we weren’t quite on the same page and I deleted her and the photo’s. Next please..

First impressions count and my most memorable ‘photo fail’ was also during this first month back in the saddle, when air traffic control granted landing rights to a 5-foot 9 curvaceous blonde named Holly at the O Bar in Sydney. 

As I stood there, scanning the room for my dream girl, I suddenly felt a strange tugging of my jacket.  I turned my head towards the motion and literally froze. As I looked down, I saw a figure who was more hobbit than human.  Naively, I thought that everyone would look like their photograph. Rookie mistake. She spoke, “Are you JD”?  My jaw, and my ego, hit the ground. I was completely blindsided, flummoxed and generally speechless as she greeted me with a “Hi, I’m Holly, shall we get a drink?”

I began agonising over the appropriate gentlemanly response - should I go to the bathroom and do a runner? We walked to the bar area and she scrambled up the bar stool as I stood there thinking (wishing?) “Am I getting a migraine?”.  She ordered a cocktail (Hobbit juice?) and I ordered a glass of wine. My brain, which is normally pretty agile, froze. The inner lawyer decided to call her out on her deceptive and misleading conduct.  “You don’t look like your photograph, and in fact it isn’t you in the photograph at all… why would you do that?”  Her answer was confronting but disarmingly honest. She said, “if I put a real photo of myself up, I know I would never be able to meet anyone… I know I’m ugly.”  

This was not the girl of my dreams, or the George Clooney moment I imagined, this was a nightmare.

We started talking about internet dating and she filled me in from a Hobbit’s perspective. It was crushing to hear that she had been on many a similar date, and managed to get lucky on most occasions with no second date or communication post. Random hook-ups if you will. I left alone and made a mental note - next time, more DD and less DM. For the uninitiated, that’s due diligence. I did not have sexual relations with that Hobbit.

Determined not be be disheartened I continued my quest and met at least 3 to 4 women a week at various bars and restaurants across the east. This was my first month back on the town after 20 years and I was wanting to experience everything on offer.

I went to a wine festival at Sydney’s Darling Harbour. There must have been hundreds of people at this function. I went with one of my reliable gay wingman and we set out to patrol enemy territory with a quick sweep of the room. It’s great to have a gay wingman, there is just no competition when you are locked and loaded. It was on this first run that I noticed a beautiful tall brunette. Our eyes met for just long enough to know. You know when you know. There was something about her that I couldn’t quite put my finger on. She was tall and exotic looking, with just enough cleavage to command my full attention. I am a nature lover and the call of her grand canyon beckoned. I did two more laps and tasted some wine. On each occasion I scanned that particular area where she had been standing and, yes, she was still there and yes, that winsome glance in my direction. I prepared to engage, moved closer and then made my approach. “Hello there…” Lame but generally effective.

Soon the banter began, but something seemed wrong. Finally, she said, “I need to ask you a question.” I said, “Of course”... she said “Why didn’t you call? You said you would call me?”. Then the bomb hit as she continued, “We went out on a date four weeks ago and had a great time and you said you would call, and you didn’t!” And then, everything came flooding back like a bad oyster.

We had met at the Establishment for a drink, she impressed me with her personality, she was full of the Eastern Suburbs filler and yes she had an impressively distracting cleavage, maybe that is what I noticed again this time.. Needless to say, we did not meet again.

So that sums up one month back on the bike, and month one of 10 years of my search for the ‘one’. There are so many more stories to tell. Many shocking to the point of being literally unbelievable.

Never give up on love.

J D Watt

Author of Burnt

Sydney Lawyer, writer and unlucky in love.


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