Dating woes of a dating wuss.

I’ve just returned to the dating world after a three year hiatus. Back in February 2015 I decided to be single for a while; no profound reason except that I knew I wanted to move cities in the near-ish future and that I was tired of it all… tired of the same old process of meeting a guy; explaining my life story; one of us falling in love; followed by the inevitable heartbreak – usually caused at a really inopportune time on my part (my last three boyfriends were handed their sentences – or rather given their freedom – on Christmas Day, my birthday, and Valentine’s Day, respectively. Maybe not so respectfully).

They were great guys. Incredible guys. I don’t think I’ve ever dated a man who was not extraordinary in some way and most importantly, kind, in many ways (apart from perhaps one bad egg somewhere on the list.) I still love most of them very much and think of them fondly for the people they are, the things they taught me and the special times we shared together. But I’ve always been a fiercely free spirited woman on my own mission and so my plan to be free and single escalated from a few months to a few years… three years, to be exact.

That’s a lot of time. Enough time to forget how this whole dating story works and to return to a world in which you tap a pink flame on your phone to browse through a catalogue of men at the convenience of your fingertips. A world which has never attracted me in the least. As much as my friends tried to encourage me to sign up, I’d never been open to the idea of Tinder – I can’t explain exactly why; it’s just not my style. Maybe I simply haven’t been ready to start dating again. Maybe I’m a little scared of putting myself out there like that. Maybe I feel that my love is too deep to be channelled through such technological trivialities; the romantic in me trusts that things will happen spontaneously and organically.

So I decided to play the game the good old fashioned way that I knew and with which I felt comfortable… by hitting the nightlife in my new mother city of residence (previously I had been living a life of quiet solitude on a smallholding in Jo’burg, and more recently a life of radical restfulness at a retirement home in Somerset West with my parents…) Things were about to change, and drastically. I swapped my usual Friday night attire of baggy track pants and T-shirt for a girly dress and white takkies and a dollop of make-up. My friend Em and I ventured out to Sgt Peppers on Long Street where I met ze German guy. Let’s call him Rudi. He was tall, cute and very enthusiastic on the dance floor – a quality I find especially attractive. We danced and laughed together until I realized that this was probably going to be my first kiss in three years… I tried to keep my expectations in check. It turns out I shouldn’t have had any at all… Rudi stuck his tongue in my mouth like an insect stabbing at food and pulled it out so fast I felt something akin to the bemused indignance of being ‘poked’ by someone on Facebook.

“What the hell was that?!” I asked.

With eyes darting around the room, he replied, “My girlfriend iz here somewhere…”

WHAT?!! He had a girlfriend, and she was right here in this bar the whole time he’d been dancing and flirting with me?! WTAF. I mean I wasn’t expecting to find Prince Charming and hear violins play a rendition of Pachabel’s Canon when we kissed, but this was ridiculous. And what a way to break my three year drought. It’s like feeling a wet splash on your head in Cape Town and looking up hopefully; only to discover a cloudless sky and that someone just spat out the window of their second story apartment.

My apologies to the poor girlfriend of this schmuck!!

Time to leave for greener grass. Otherwise known as Deco Dance. We were old but the night was young and we found a sea of men (not seamen) to float around in; there were so many different types of guys and they approached us with the consistency of waves. A young one caught my eye and then my hand as he twirled me around the dance floor to Whitney Houston’s I Wanna Dance with Somebody! and Grease Lightning’s Summer Lovin’. It was all so romantic and I felt a spark stirring… then he leaned in close to me and announced he was leaving to get a shawarma.

So I kissed him, and with a broad smile on his face he said he didn’t want to go get a shawarma anymore. This boy was cute, and young. Super smart, too. Let’s call him Brain. I found him even more attractive when I learned that he’s a doctor and seven years younger than me. Seven! I used to date men who were way older than me but as my years have increased, theirs have plummeted in inverse proportion to the point where I think I am now playing in cougar category… to my amusement and delight. I didn’t tell Brain my age but he said he thought I was “around 24 or 25.” Oh my god I love you, I said to him (silently) as I high fived myself (in my mind).

Around 4am the music stopped and we were kicked out of the club, so we sat on the streets of Sea Point and chatted with Brain ‘til the sun rose. Em and I strolled home, eventually getting to bed at 6am and I chuckled as I thought of most of my friends who were just getting up around this time on a Saturday to attend to their kids…

I love my life.

Soon after this first all-nighter, Brain and I went on two dates together and I felt like something was starting between us… he texted often and impressed me with what seemed to be – aside from an obviously high IQ – also an elevated EQ. He made me smile and I thought to myself, I might just want to keep this toy boy…

And then he ghosted me.

‘Ghosting’ is a term I’ve heard millennials use for when a guy seems ‘totes’ into you but then suddenly vanishes without a trace – no explanations; no communication; nothing. Gone. Like the wind. Like a Phillip Phillips song. Like that girl in the movie. I do not date guys like that. But after being in touch daily for a while, Brain flew to Durban for ten days and I never heard from him again. He must have lost his phone in transit. The poor guy probably got mugged. Wait, no – I’m sure he was actually sent out on an urgent relief-aid mission to a war-torn African country where he was performing life-saving emergency surgery on children before being captured by rebel soldiers who were now holding him hostage! So he obvs couldn’t text me:)

Orrr… maybe his name should just be Doctor Douchebag. Perhaps the seven year age gap was indeed pushing it a bit and my fantasies of frolicking in the doctor’s office with my new toy boy promptly dissolved into a hazy cloud of age-related realization that I hadn’t been ready to acknowledge… and so with the swiftness of Taylor I shook it off and got ready to meet the next one. I decided to quit trying to understand the vagaries of twenty-something-year-old boys’ hearts and minds and move on, once again, to greener pastures…

The next time I went out it was to Harrington’s, an upmarket bar in town filled with style and sophistication. And me; in my little floral age-defying (denying?) boob-tube dress and alice band and not-so-white-anymore takkies. This was a mad fun night of getting down low and dancing like crazy to old school hip-hop tracks with my friend Eves and a bunch of energetic strangers. In the early hours of the morning I ended up kissing a very good-looking forty year old Australian who was the most complimentary man I’ve met in a long time. He was smart, sexy, and full of sweet things to say about me… and he was heading back down under the following day. Ohhh well, it had been another super fun all-nighter and I smiled as I headed home in an Uber not long before sunrise.

At some stage during these weeks I noticed that my same-aged neighbour, who had just moved into the flat next to mine, was actually a bit of a looker. It turns out he has the same name as Doctor Douchebag and also happens to have a doctorate in his field of study. But at least he has seven years on Casper. Let’s call him Brain Two. He’s high energy, highly intelligent and also highly arrogant, I thought at first. I walked past his apartment late one Friday night after seeing a play and complaining to my friend about the youth of today. She spent most of the time trying to convince me to join Tinder, meet hordes of men (not whores of men, I’d hope) and enjoy multiple free drinks and meals. Enter, the living antithesis of this ideology: Brain Two. Or rather, I entered Brain Two’s apartment, as he invited me in for a drink and two hours later we were still debating the intricacies of Tinder, dating and who should be parting with their cash (he is vehemently opposed to paying for girls on dates as he asserts that we are all equal, while I still enjoy the old romantic notion of chivalrous men picking up the bill. This is an ongoing, heated argument between us…)

Brain Two has me vacillating between my opinions of him and whether I like him or not. I think that he likes me as he texts me all the time, but I can’t be sure and after my experience with Brain One I realize that my attraction barometer must be pretty fucking faulty. So Brain Two was put into the Friend Zone from the start. After all, we are practically roommates, so getting together is likely a terrible idea; and we disagree on everything from dating and money to diet and God – probably the fundamentals on which people build their relationships together and not the ideal circumstances in which to be catching feelings for someone with his Byronic nature…

We’ve basically been fighting about stuff since we met but I think we both enjoy our stupid banter and sarcastic humour. Also, he’s been helping me navigate the world of Tinder. Ironically I’ve only ever opened the app whilst in his presence and then he grabs my phone and starts swiping right like he’s playing a video game. And that’s as far as I’ve progressed on the pink flame: a few random matches but mostly general app apathy. I’m still slowly warming to the idea… my tinder ain’t flamin’ just yet. In the meantime my neighbour has been keeping me busy enough…

One weekend Brain Two was hosting his friend’s friend from Canada, a girl who works for Doctors Without Borders and who was in Cape Town for a night, so he invited me to join them for drinks. It was a Saturday evening around 8pm and I was having an early one: already in my pyjamas and in bed with my book (books are all I go to bed with these days). I was in my lazy mood so it took some convincing, but my fast-rising FOMO coupled with an opportunity to go out on the town versus the thought of staying in bed and reading about my friend’s erectile dysfunction had me painting on some make-up and throwing on some party clothes within minutes… (I have deep respect for this new author and his work in the beautiful Butterfly Man; and I know he’ll humour the tongue in my cheek here – but it was a Saturday night and this butterfly wanted to socialize;)

That decision led to one of the funnest and funniest nights out I’ve had in a long time…

The Canadian girl – let’s call her Dana – was a breath of fresh air to meet. She’s a smart, beautiful brunette with a shiny stud in her nose and a sparkle in her eye; a bright bundle of energy who’s even more enthusiastic than me on the dance floor. We took an immediate liking to each other. There we were – basically three strangers – bar hopping together like old friends. We had dinner at Tiger’s Milk and in an ironic twist of fate Brain’s bank card was declined so I ended up rolling my eyes and paying for his meal. Then Dana and I somehow managed to talk the doorman into waiving the R100 entry fee for men at Harrington’s and allowing him into the club for free. Brain Two was living the life of his dreams.

We drank cocktails and danced until it was time to move on to the Village Idiot, where Brain wanted to meet up with the girl he’d been seeing via Tinder – let’s call her New Zealand, because she’s from New Zealand (“She’s international, she doesn’t expect a man to pay for the bill on a date,” boasts Brain while I roll my eyes so far back I’m nearly blinded). But upon seeing him there with the two of us girls, New Zealand burst into a jealous rage and gave him an ultimatum that resulted in them breaking off whatever they had. So the three of us promptly decided to leave the Village Idiot, and like the village idiot I missed the step off the balcony and face-planted flat onto the floor in front of everyone. Darling Dana pretended it was a purposefully executed dance move and threw herself down too; then with one swift swoop pulled me back up on my feet as we roared in fits of laughter.

Our final port of call was a grungy club called Aces and Spades. We joined two of Brain’s guy friends there and the five of us downed cocktails and tequila shots as we hit the dance floor hard. The music was great so I was all over the show. At one stage I gained an appreciative audience whilst side-planking in the air on the DJ’s shoulders! Yes, this was the fun old Tess I think I lost a little in my years of sequestered spirituality. This was me in my element – expressing my jubilant silliness and dancing like no one was watching. Soon, everyone would be watching, as what happened next took even me a little by surprise…

I had scanned the bars for any potential hotties, but alas, Cape Town wasn’t showing off at all tonight. And Dana and I had hit it off so well that I started to look at her with a sparkle in my eye. I’ve always admired the elegance of the female form and found that certain women exude a subtle sensuality that I find alluring. As Dana and I were grooving together on the dance floor I realized I wanted to kiss her. I mean, maybe it was the tequila that wanted to kiss her. Either way, this dark and grungy club was the perfect place to let go of inhibitions and surrender to such sensibilities. She pulled me off the dance floor to a corner of the bar where we made out with each other between bursts of giggles and tender arm strokes. The guys, thinking that we were buying drinks, came to find us… they found a little more than they had bargained for;)

This was definitely not how I envisioned the night unfolding a few hours ago when I agreed to get out of bed and join them for a few drinks, but it was surpassing my wildest expectations and I could not stop laughing. I hadn’t kissed any girls since my teens and early twenties and I was loving reliving my youth! It was 3am and the music stopped too soon. The DJ high fived me and Dana kissed me and we all stumbled out onto the streets together like a bunch of drunken teenagers. It had been an eventful night to say the least.

The funniest part of this story is the love triangle – or whatever awkward shape it was: New Zealand had wanted to get with Brain but threw a tantrum because she saw Dana and I as a threat; then Dana had frankly asked Brain if she could hook up with him but he had just as frankly declined her; then I ended up getting together with Dana, who actually happens to be married but in a very complicated, open relationship with her bisexual husband who thinks he may be gay and whom she’s given the space to explore… so on a night that I had planned to be in bed reading a book about flaccid penises, I ended up going out to four different bars with two people I hardly knew and making out with a married woman (insert any number of consecutive laughing emojis here. And maybe also the one with the two women hearting).

OMG. I guess I’ve got a story to write.

It didn’t exactly fulfill my notion of romance but I suppose I got the spontaneity I’ve wanted… impromptu parties often end up being the best fun and suffice to say that things did happen organically throughout this ridiculous night (wo/ man am I glad I got out and lived a little!).

But kissing guys who have girlfriends or who turn into ghosts or who live on the other side of the world – and kissing girls in general – is not exactly helpful to my dating life. Quite a few weeks have passed since then and I still haven’t found the impetus to start going on Tinder dates… until now.

I think I might have finally melted the ice and relinquished my resistance to the pink flame. It’s nearly winter so I’m going to throw myself into that fire. Maybe I’ll meet some decent men. Maybe I’ll score some free meals. Or maybe I’ll just come out with some more stories to write… 😉