A few minutes later I was kicking empty water bottles off the back seat of a stranger's car and feeling decidedly less happy and content with my life choices. As the Uber my gentleman friend had so generously called for me pulled away from the footpath and became instantly stuck in a traffic jam, I stared out the window and pouted.
For a girl from the suburbs of Melbourne, Sydney was a bustling metropolis and I'll admit that I may have had a slightly romanticised view of my new city. But now, having been freshly booted from a bloke's bed and in to the back of a ride-share vehicle, I felt less like Marlo Thomas in That Girl and more like Amy Schumer in Trainwreck.
Over the weekend I bumped in to my friend Lucas* at a party, who sympathised with my recent complaints about the difficulty of dating in Sydney. When he moved here from the UK he didn't know that many people, so as far as dating was concerned, the city was a 'blank slate' to him. He downloaded apps, he went to parties and bars, and he got to know people through his social and work circles.
"In the five years I've been here, I've not managed to form a relationship, nor have I dated anyone for longer than a few weeks. I have, however, had heaps of hook-ups," he told me. "I'm level-headed, reasonably intelligent, I look after myself, and I have my own place, so I've started to ask myself: does the problem lie with me, Sydney, society in general, or a hybrid of all three?"
Lucas and I have had similar experiences dating in Sydney; but his outlook is far more optimistic than mine.
"I think I'm more than satisfied with what I've got: a great group of friends, a wonderful job, an amazing apartment. If Sydney didn't offer me these things, would I then look towards a relationship? Maybe," he said.
"I think the question for me is what would a relationship offer me that Sydney doesn't already offer me? What I do know is that I wouldn't want to make sacrifices."
The more I spoke with Lucas, the more I realised that maybe he was on to something. Instead of getting hung up on the pitfalls of dating in Sydney, he had used it to his advantage: having enjoyable hook-ups and fun short-term relationships while he prioritised his career, health, and social circle. When I lamented Sydney's dating culture — or lack thereof — I wondered if maybe love was on its last legs.
But now I'm beginning to think that maybe, it's simply evolving.
I got myself another drink and started talking to Steven*, who has been with his partner, David*, for six years. While they're in a strong, committed relationship; they also have an established 'free pass' system for sleeping with other people.
"Six months in to our relationship, during our first overseas vacation together, I disclosed that I didn't think I could commit to lifelong monogamy," Steven said.
"I reassured David that I wasn't suggesting opening up our relationship only six months in, but told him that one day in the future — whether it was in two, five, or six years time — I would likely bring up this topic again."
And he did. Steven and David are now happily non-monogamous, and have an established set of rules that permits casual sex when either of them are out of town or travelling for work, which they frequently do.
"I had begun to consider those people who clung to monogamy in a relationship, no matter the toll, to be extreme; rather than me for considering non-monogamy," Steven explained.
"A successful monogamous relationship just means you won't have sex with another person until one of you dies. And I don't want my partner to view being with me as a restriction on his life experience."
Steven and David made the mutual decision to open their relationship up to casual sex with others, and found that it benefited them; while Lucas enjoyed hook-ups and flings without letting them distract from the life he had built for himself in Sydney.
On my walk home, I began to think about that man who had, so many years ago, hustled me out of his bed and in to an Uber home. For years I told the story of our evening together and for years myself and my friends laughed at his abruptness and apparent tactlessness. But I began to realise that maybe, he had the right idea all along. While my ego certainly felt bruised at the time, I've had more than a few hook-ups since when I've found myself thinking that I, too, should summon a car to take my date away and let me return to my evening.
Much like Lucas, I may be single but that doesn't mean my life is in any way lacking. I work hard, I have great friends, and I spend a lot of time by myself doing things that I love, and that keep me happy and healthy: I travel, I work out, I go to classes. My life couldn't be further from empty, in fact, sometimes it feels so full that there's no space for anyone else. Still though, I don't fancy the idea of celibacy, and forming a long-term relationship with my vibrator hardly sounds appealing.
Maybe, all this time, I had been viewing Sydney's attitude towards casual relationships as a problem: when really, it was a solution.