How a holiday helped me let go and learn to enjoy flirting

What is it about holidays that makes flirting seem so much easier?

Let me set the scene. I’ve just arrived in Byron Bay, my first holiday in a year. I walk into a cafe with a friend and we find a table near the window. It’s about 3pm. We sit down in a booth, and as we’re perusing the menu, a really cute waiter comes up to the table.

He stares at me, intensely, like I have food on my face. He smiles and asks if I’ve made a decision. I say, “No, not yet.” And because his eyes are so warm and friendly, I smile back at him. 

Then he winks at me. Whaaaaat. Is he flirting with me right now? He comes back again a few minutes later and WINKS AGAIN. I awkwardly try to flirt back, but after seven months in lockdown, I am incredibly uncomfortable.

No one has ever winked at me before. In fact, I don’t remember the last time someone flirted with me so overtly. It must’ve been the last time I was on holidays. I knock something behind my head and he laughs at my awkwardness, winking at me a third time. I go completely red and just want to disappear. I berate myself. Why can’t I just be… cool? 

A few days later, I’m walking back from the beach and a guy stops me in the street. “Windy, isn’t it?” he says. We stand there for a few minutes, chatting away about the windy weather. Talking about the weather has never been as sexy as it is right now. When you’re in the moment, flirting can make even the driest of topics seem salacious. 

I walk away, wondering what just happened. While I’m not 100 per cent sure, I’m fairly confident two guys have tried to flirt with me in two days. That’s two more than in the last few months. 

A few weeks go by. I’m finally relaxed. Work is a distant memory. Everything slows down, including my mind. My movements become slower; more intentional. Soon enough, my friend has to request that I stop making ‘sexy eyes’ with every cute guy I encounter. I protest like a child. “I’m not making sexy eyes! These are just my eyes… I can’t help my eyes!” 

This is what always happens to me on holiday. A slight shift in my energy, and suddenly flirting comes a little more naturally to me. Once I went a whole year without both a holiday and flirting with someone – and everything else that comes after flirting, if you get my drift.

I remember telling my therapist, “I don’t understand it. When I’m home, guys just don’t speak to me. They don’t flirt with me. They don’t seem interested. But as soon as I go on holidays, boom… A guy will literally run after me in the street to ask me out for a drink. I think there’s something wrong with the men in Melbourne.” 

She responded, in typical therapist fashion, “Maybe it’s not the men. Maybe it’s you. On holidays, you probably start to relax, and you may appear more open. Maybe you’re not giving off any signals in Melbourne that you’re open to getting to know them.” 

No, that can’t be right, I remember thinking. It’s definitely the men in Melbourne.

I recently spoke to love coach Shaun Galanos about flirting with confidence, for my dating podcast Single Minded. He has an online flirting course, and the language really resonated with me. Unlike online articles that suggest all the usual techniques like touching someone’s arm, or staring into their eyes, or asking them lots of questions, Shaun talks about authenticity – about having fun and about kindness and respect. 

A sentence in his course outline sparked something in me: “How can I get more comfortable with small talk while staying genuine?”. And then it clicked. I suddenly remembered that conversation with my therapist. Is it me? 

When I’m on holidays, my entire body relaxes into itself. Suddenly, small talk (like the weather) becomes easier. I feel comfortable with myself. Flirting is no longer stressful because I’m no longer pretending to be someone else. 

Dates in Melbourne feel like interviews for me. Usually, it’s after a long day at work. I’m all in my head; sometimes I’ll be questioning myself because something happened at work that has knocked my confidence.

Or I’ll have looked at myself in the mirror before the date and shit-talked my appearance. I feel like I’m trying too hard to be someone else. I forget that if I end up dating this person, eventually they’re going to have to get to know the real me. 

Flirting, to me, has always felt like a loaded word. I associate it with acting; it’s about putting on a mask and trying to be someone funnier, someone sexier, someone who every single person in the world would want to date.

But the more I learn about it, the more I realise it’s really about signals. It’s about opening up, ever so slightly – just like you do while on holiday – and showing the other person who you are. It’s about them doing the same, and then waiting to see if sparks fly.

Hannah is a content creator from Melbourne. She works in the beauty industry, and in her spare time hosts Single Minded, a dating podcast that’s flipping the script on being single. When she’s not creating beauty content, you’ll find her somewhere remote backpacking overseas – preferably with no WiFi to get a much-needed break from Instagram. Follow her addiction to serums and travel on Instagram here.