The Canberra Dating Challenge

Like most millennials, I have ventured into the world of online dating. Specifically, I ventured out on online dating apps three times, over three years, going on a single date each time and promptly deleting the app when I realised it wasn’t for me. (Also a result of a horrifically stilted coffee date, a catfish, and a let down when it turned out three weeks of online banter resulted in no real-life chemistry or attraction.)

I was going to meet someone in the real world, or not at all.

So when a friend of mine dared me to a one month dating challenge earlier this year, of course I said no. But the more we unpacked it, the more I realised that I hadn’t used dating apps intentionally as a way to meet people which meant I didn’t have enough data to know what I was looking for and why. Was this single life a life that I chose, or was I just too scared to go out and meet people?

We agreed to go on a minimum of four dates with four different guys over the next month, and so the Canberra Dating Challenge was born.

The Strategy

I am competitive, and an over achiever. I was prepared to meet and connect with four different, interesting guys, as quickly as possible. And the best thing? Every first date encounter would be a success, no matter how it turned out.

I think many of us use dating apps in an unintentional manner and as a result our return on investment on our time, and therefore our success rate, is really low. I was determined to overcome the challenge, so I developed a strategy, and this is what it looked like:

  1. Download Hinge. I’d used Bumble in the past, but hated how I, as a female, always had to initiate the conversation, especially when I couldn’t get any feedback on what it was about me that interested them (assuming it wasn’t a standard swipe right session). With Hinge, we can respond to photos or to prompts instead of just sending a like, and both genders can initiate a match. Commenting on someone’s photo or prompt makes it much easier for them to respond to you, and just like that, you’re in conversation.  I was extremely proactive, and found that commenting on other people’s prompts had the best results. I also realised that if I couldn’t find anything on their profile that interested me enough to start a conversation, we probably weren’t a good match. (Pro tip: having intriguing/ conversation prompting prompts on your profile is important, and responding with a question makes it easy for the other person to engage.)
  2. Quick chat conversion rate. I wanted the quickest conversion time from first chat to face-to-face meeting, ideally within 3-5 days. This was partly because we had set a time-based challenge, but was also something I’d learnt from my last foray into online dating. There was no point in getting emotionally invested in a version of someone only to be disappointed when you do meet. I found the best approach was having a proactive Sunday match session, then focus on conversing with matches during the week, and setting up dates with the people I wanted to meet over the weekend (my weekly battle rhythm, so to speak).
  3. Filter. Even though it was a challenge, I only met people I was genuinely interested in meeting, and who I felt were genuinely interested in meeting me. I ended up setting up more dates than I went on because I ended up getting a red flag, or they changed the location at the last moment to the other side of town. I did the standard “are you a normal person or a murderer” check, and if I had to work to keep the conversation flowing then I would end it. In the end, if it’s not someone you would be friends with, or whose behaviour you would accept, or they’re not putting in a minimum level of effort, they are not the one for you, no matter how accomplished or well-travelled or attractive they are in their photos (which could be years old). I also liked to have around five conversation topics in mind when we did meet each other face-to-face, all things I wanted to learn more about based on their profile and the chat. If there wasn’t enough content to sustain a one-hour conversation, we probably wouldn’t get along very well.
  4. Keep it low stakes. Meeting a stranger, let alone one that has romantic intentions, puts pressure on everyone. I found that reframing the situation to being just a first encounter with another person who could become a friend or something more made it so much easier. Keep the dates (first encounters) simple and low key – go for a walk, grab a coffee in the morning or a drink after work. Don’t make it hard for either of you, and try to minimise the investment required while still creating a genuine connection and respecting the other person. The goal of my encounters was to see if we enjoyed each other’s company. Did we share interesting conversation? Did I get a good sense of their energy and how they engage with other people and the world, and was it something I resonated with? If things are going well, are we flirting? Are we laughing at the same things? Do we feel more comfortable in each others’ company as time passes? That’s it. That was all I had to do, and reframing it as such helped to take the pressure off needing to figure out whether they were The Love of My Life.
  5. Remember that we are people. When using dating apps, we can forget that we are talking to a human being on the other side. They are a real person with thoughts, emotions, fears, insecurities and demands on their time – even while I was doing a challenge, I was mindful not to waste anyone’s time, and not to let them waste mine. I was quite cutthroat when filtering but I always erred on the side of informing them I wasn’t interested anymore before I unmatched, and I was genuinely interested in getting to know the guys I ended up meeting.

The Result:

I went on five dates in two weeks (one was a second date) before I got really sick and the month ended.

The dates were, on the whole, lovely experiences with interesting people. All were polite, on time, focussed and interested in getting to know me (no phones out, no talking about exes, engaging conversationalists), and respectful. We split the bill, which is my preference – I only let them pay if they really insist on it and then I’d rather not make a scene – and parted on good terms.

I did learn a lot, just from expanding my comfort zone, and it turns out that being proactive and paying attention to how I responded to different people in different situations was really insightful. Here are the biggest takeaways for my future self:

  1. It gets easier. Practice makes perfect, and while perfection is a fallacy, the principle remains. On the first date I was a little nervous, and there’s always that awkward moment of “Is that them? How close does that person resemble the photo of the person I’m meeting?”, or if you’re the first to arrive, standing and waiting, convinced that everyone who walks by is them, or worse, that you’ve been stood up (which luckily hasn’t ever actually happened to me), but by the time I had my fourth first date in ten days, I was just excited to get to know someone and wasn’t focused on what the outcome would be.
  2. Know your first date preferences. I sampled a range of date styles as part of the challenge – brunch, walks, drinks on a Friday, drinks on a weeknight – to figure out what type of date brought out the best in me. It turns out my favourite date was a patisserie followed by a walk in a trendy suburb I didn’t know too well. Between the sugar rush, exercise, and discovering a new place, I wasn’t nervous, there was plenty to talk about, and it was a fun way to get to know someone (particularly noting that it turns out we were absolutely not compatible but I learnt a lot about fire safety and emergency management).
  3. Assume there will be a second date. Even though it was a dating challenge, my approach going in was that each date would have a second date unless there was a reason not to (e.g. poor behaviour, genuinely not compatible even as friends, lying about who they are). This helped to take the pressure off deciding whether or not there’d be a second date because… I’d already made it. Instead, I could focus on connecting with them and get a sense of their character, and whether they were someone I wanted to spend more time with.
  4. I’m monogamous. Like, really monogamous. I struggled just with having a first date with one person and a second date with another – let alone knowing that I had an active account on Hinge while I was meeting both of them. While having multiple first dates and conversations running in parallel made me less emotionally invested in any one particular outcome in the beginning, later I felt like I was misleading people, and it reemphasised that I’m just not cut out for online dating multiple people.
  5. Dating is emotionally draining. Dating, especially at this intensity, but even with any degree of intention, takes a lot of time and effort and emotional attention. I started strong with three first dates in three days and after the third, all I wanted to do was hang out with my friends, in my favourite bar, where I could be myself (as opposed to the best version of myself), and I knew I would have a good time. In future, I’ll probably take it slow, maybe meeting one person a week (let’s be honest, a month), and in all likelihood, someone I’d already met in the real world so I could get a sense of who they were and their energy.

Will I continue online dating? Probably not. I didn’t really like who I was when I was using the dating app, judging someone based on a two-dimensional image of who they are and commodifying their existence. It reduces us to a surface level assessment of who they are and who we are and so I think we miss out on meeting some great people, and finding the best in each other.

It also turns out that I love my life, just as it is. Between work, study, latin dancing, hiking, and improv, I’m fulfilled, content and have a wonderful community and rich relationships. Much as it is nice to share one’s life with someone, I don’t actually need them to be happy, and so was content to walk away from online dating having completed the challenge.

And who knows – my next first encounter in the wild might be just that, an encounter, or it could be the beginning of something wonderful.