Dating Disasters & Quarter-Life Crises: The Convos That Call For A Glass Of Vino

During lockdown, we all developed a knack for turning boring small-talk into actual conversation. Mainly because all we had to talk about were our silly little walks, TikTok (Thank God for TikTok) and the culinary masterpieces we cooked up after finding them buried deep in our Instagram feeds. 

It felt like our real lives were on pause for a while there, and so were those early dinners that turned into late nights because the conversation flowed as freely as the wine. The ones where we were convinced we were going to solve all the worlds problems (or at least my relationship ones) in one sitting. 

I think those are the conversations that I missed most during lockdown. Which got me thinking about all the late-night conversations with friends that have helped shape my life. Some of them have been chaotically good, like the night I decided to move to LA and bought a flight right there at the dinner table. While others, I poured my heart out over a glass of vino after just having it absolutely obliterated by yet another failed relationship. We’ve all been there. 

Good or tough, these are the conversations that help form your opinions, grow as a person and become who you are. Here are just a few rolling conversations that I’ve had time and time again, and yet each iteration has changed me in some way for the better. 

We’ve all walked away from some seriously disastrous dates and thought, “Well, at least it’ll make for a good story”, while furiously texting the group chat to meet up for a debrief. They’re the kinds of conversations that have you howling with laughter deep into your glass of wine (in my case, a Brown & Co. Rose). Your single friends are doubled over, nodding, relating to every word. While your mates in relationships look at you like you’re a cautionary tale, side texting ‘i love you’s’ to their significant other. 

Once the laughter subsides, the good advice starts to flow. Everyone leans on their own life experiences (to get over, get under etc.) to help console you. You usually walk away ready to swipe again. 

I don’t know when or how it happens, but there comes a day where you look around (or scroll through social media), and suddenly it feels like everyone around you is either rocking a baby or has a rock on their finger. At that moment, you start to question everything. 

When this happened to me, I called up my closest friends, who promptly arrived at my tiny Sydney apartment with cheese, vino and sage advice. 

The reason your friends can talk you out of this “left behind” anxiety spiral is because in your twenties and thirties, you cultivate friends around you who want the same things in life and are generally on a similar timeline to your own. Sure, they break off and do their own thing over time, but they’ll always have the ability to understand where you're at in life. 

I don’t know about you, but I’m generally pretty bad at reflecting on how far I’ve actually come since high school. We all reach a point where we start to question what we’re actually fucking doing. For some of us, the ol’ quarter-life crisis happens fresh out of uni. For others, it happens after a few job changes or failed relationships. For me, it feels like it happens every 3-5 years when my crippling anxiety likes to remind me that I haven’t “achieved” what my younger self thought I would have by now. 

This is where my friends often pop over to console me on my bathroom floor and remind me of just how far I’ve come. These are the conversations that ground you back into reality. The ones that remind you that while you might be lacking in some things, you still achieved great things and have plenty to be grateful for at the same time. They also serve as a reminder that you don’t have to have all your life plates — job, relationship, friendships, money — spinning all at once. 

This might be the conversation I’m most fond of. The one where you’re enjoying a wine or two, surrounded by your favourite people and everything thing you’ve ever dreamt of doing, feels like it’s at your fingertips. You make those grand travel plans — Spain! Mexico! New York! You run all your amazing side-hustle ideas by your friends while exclaiming how you can’t wait for it to make you millions! Or my personal favourite — you text that person you’ve been daydreaming about a future with a tipsy confession or two, knowing full well you’ll regret it in the morning. 

Whatever it might be, these are the conversations that let you dream about what life can offer you. Who knows, something said in these moments might manifest into the life you’ve always wanted, so why not say it out loud?! 

If you’ve made it this far and your mind is swirling, thinking about all these kinds of conversations in your own life, congratulations. You’re doing it right, my friends. Life is all about connecting with the people you love, showing up for each other and showing up for ourselves. And if that takes shape in the form of dinner, vino and endless conversations with friends — I’m very grateful it’s back.

Cheers to your next early dinner that turns into a conversation-filled late night IRL.