The Tinder Fling That Turned Into Something Less Terrible Than Expected

It all started on Tinder, a place where love is fake, connections are questionable, and all men who say “Hey, I’m just looking for something casual” really mean, "I’m gonna try to make you fall in love with me after three days." We were no exception.

We were two men who had clearly given up on ever finding a decent date but still enjoyed the thrill of rejecting men with bad pickup lines. Then, we saw each other's profiles. At first glance, we thought, Okay, they’re cute, but let’s not kid ourselves—this is a weekend-only thing. He looked like someone who could handle just a sneaky weekend. Like a Netflix-and-chill situation with zero promises beyond a good time. A deliciously uncomplicated fling.

So, after a few days of awkward small talk (because let's be real—Tinder conversation is either a slow death or an instant "let's skip the formalities and meet up"), we settled on a Saturday night after Brayden had a rather fancy evening at the Crown, all dressed in a suit, we might add. We both had the same idea: drinks, awkward small talk, questionable hotel choices, and breakfast... followed by never texting each other again. Simple. Elegant.

Connor picked Brayden up out front of the Crown Casino Marquee, and we made our way to the Aloft Perth so Brayden could slip into something more comfortable. Then we headed to a bar that smelled like regret and whiskey—our kind of place. We were two Aperol spritzes in (which, later, Connor found out Brayden hated), that sweet spot between “I can still walk” and “I’m suddenly really confident about making terrible life choices.” We were just standing there, looking like we had no intention of making small talk, but the smirk said otherwise.

Connor bought the first round like the well-brought-up gentleman everyone knows, and Brayden made a mental note to marry him later—if he was ever capable of not being an asshole.

After the drinks (and some surprisingly deep philosophical musings about why pizza is the superior food), we ventured into the cold night air. There, in the alley behind the bar, Brayden offered Connor a cigarette. Because nothing says “this is going somewhere” like sharing cancer sticks in the dark. We leaned against the brick wall, and for a second, it felt like maybe this wasn’t just a random hookup. We didn’t talk much, just exchanged a few words that were likely useless but felt profound at the time.

Then, of course, the inevitable happened: we made our way to a hotel. (Shout-out to Hotel “We’re Definitely Not Getting A Refund,” where the sheets were 75% clean but 100% uncomfortable.) We stayed up late (or early, depending on how you want to look at it) doing the usual hotel-room tango.

The next morning, after approximately four hours of sleep, we both woke up like two people who had just committed crimes they could never explain. There was no need to exchange awkward small talk.

We had breakfast together. It was probably supposed to be a romantic, “let’s see if there’s more to this” moment, but it felt like an audition for an insurance commercial. The eggs were cold, the coffee was mediocre, and we both tried to act like we weren’t secretly just relieved that the weird morning-after anxiety wasn’t making either of us immediately want to flee the planet.

We parted ways with a “Hey, it was fun. Maybe I’ll see you around?” and a half-hearted hug and kiss, which, looking back, was less like a farewell and more like the weird side hug you give your cousin who just told you their idea of a great first date is to go see a live penguin exhibit.

And then… nothing. For days, it was as though we had both agreed on a “No Contact Clause” for our weekend rendezvous. A silent pact, if you will. Then, of course, exactly a week later, like the predictable fools we were, after only being “single” for seven weeks prior and not looking for anything serious, we both sent the “Hey, how’s it going?” texts. We had managed to go the whole week without speaking, like two people who hadn’t just ………. for several hours, but you know… we played it cool.

We both told each other about our weeks, blabbed about our best friends, emotionally dumped, explained our profound love of our cats to each other... then the next weekend, we ended up staying at Connor’s house. And by that, we mean, we didn’t even know if we wanted to sleep with each other again or just keep making jokes about how terrible we both were at casual hookups.

Three years later, here we are. Laughing about how the whole thing started as a Tinder game. Now, we’re not just the guys who drunkenly shared a cigarette or the dudes who managed to convince each other to stay in a hotel that could’ve been condemned if someone had the time to file a report. You’re actually the guy I... still casually sleep with, but now we share more than just bad hotel breakfasts and questionable decisions.

And as for that weekend? I guess we proved that sometimes a “sneaky” fling can turn into something... a little more sneaky than expected.