My friend and I made a resolution to ask someone out in person every month. We failed

Last December, after consuming a few red wines, my friend Hana and I set ourselves the new year resolution to ask someone out in person each month.
With Hana visiting Melbourne from Canberra a couple of times a year, it was typical for our boozy biannual catch-ups to end in questions about our dating lives. This night was not much different.
But as we filled each other in, nestled in the booth of a Brunswick bar, we both expressed a desire to branch out from the world of swipes and DMs that we’d become accustomed to.
Not that there’s anything wrong with a good ol’ swipe, of course. But Hana and I, both 28, had been discussing certain instances in our lives in which we’d been out somewhere and met someone who we were attracted to, only to part ways with them, not say something, and immediately feel a sense of regret.
“Ah,” we’d ponder, as the potential loves of our lives marched off into the abyss, “What if …”
We also agreed that asking someone out in person would be the ultimate test of courage. How comfortable were we to put ourselves out there and potentially face rejection, delivered to our faces?
There were stipulations for this resolution: the asking out had to be done in person (some classic IRL vis-a-vis) and the person had to be a complete stranger – someone we might’ve met at a coffee shop, for example, or a bar.
These stipulations, I quickly came to realise, would prove rather difficult. During those first few weeks of January, there were certainly instances in which I could’ve actioned the resolution if I’d been brave enough. I’d spot someone across the room at a bar, or a friend would bring someone along who I hadn’t met before. “He seems nice,” I’d think to myself, immediately ruminating over my promise to Hana.
But every time I envisioned swallowing my pride and handing out my number, the dreaded doubts would rear their ugly heads. Did he have a partner? Would he feel embarrassed by my expression of interest? Was he even into guys?
As it turns out, Hana wasn’t having much luck either. As time passed, we’d routinely check in with each other, tails between our legs.
“Did you ask anyone out in person this month?” I asked Hana at the end of January.
“I conveniently avoided asking,” she said.
A month later, at the end of February, we reconvened. “I didn’t do it,” Hana admitted, “but March is a new month.”
“March is a new month,” I agreed, feigning optimism. “We can do this.”
We’d laugh. Each exchange of messages began to serve as a monthly reminder that we were, in fact, flopping.
I would eventually go on several dates over the subsequent months but all of them were either initiated over Instagram or dating apps, or with guys I already knew. Take boy 1, for example: he slid into my DMs after a friend of his suggested that we should meet. Boy 2? We’d known each other for quite a while and I sent him a message after we ran into each other at a bar. Boy 3? We’d matched on Hinge.
All of these instances, albeit great dates, obviously failed to qualify for our resolution. And now it’s August, meaning eight painstaking months have gone by without Hana or I asking someone out in person. It’s safe to say that our mission has failed dramatically.
Hana admits that one reason for her failure to approach someone in-person this year was the knowledge that she could “fall back on the apps” if need be. But in instances when someone did catch her eye, she admits, like myself, that a fear of rejection often held her back.
“Even though I know that if someone asked me out in real life I would never be rude to them and would politely decline if I wasn’t interested,” she muses, “all logical thinking leaves my body when I’m looking at an attractive person.”
We talked about potentially shifting the goalposts to make the challenge more doable: asking someone out in person just once this year. Just once. That’s all.
But even then, I’m nervous! Can I blame my phone addiction for making me unable to converse with strangers in person? Can I evade accountability under the guise that asking someone out in-person just isn’t the status quo any more? Can I still play the pandemic card?
As much as I would like to use any of the aforementioned excuses, these past eight months have proven that I’m the only person to blame. As it turns out, I’ve preferred to stay in my comfort zone – it’s really comfy, after all.
So, for now, be it for better or worse, I think I’ll stick to the world of swiping and DMing. But I hope to eventually embrace vulnerability, put myself out there and express my interest to attractive people IRL. In 2025, or 2026 … maybe.