I ditched the dating advice and went to Thailand instead
What happens when everyone else falls in love but you book a flight
According to the internet, having a boyfriend is uncool now. This is wild because I spent years convinced that not having one meant something was wrong with me.
This week, a Vogue article went viral, asking Is Having A Boyfriend Embarrassing Now? Apparently women are avoiding posting online about their relationship because having a man takes a hit on your street cred. It concludes being single is seen as “a desirable and coveted status.”
Where was this energy when I needed it? Years ago, my long-term relationship ended, followed by disappointing dates and attending everyone else’s weddings alone. Tired of it all, I went to a workshop to learn how to finally attract my perfect man.
But instead of finding Mr. Right, I ended up going for dinner by myself and losing my shoes on a beach in Thailand. Turns out, that’s exactly what I needed.
The timeline panic
The milestones are clear. By your 30s, you should be settled. Partner, property, pension: the holy trinity of acceptable adulthood we’ve all internalised.
My relationship ended right as I turned 30. Everyone around me was getting engaged, buying houses and having babies, while I felt like I was falling behind. Which is why I went to the dating seminar, hoping for a quick fix to my love life.
Despite this being one of the cringiest moves of my life, I wasn’t alone. The hotel conference room was packed with successful professional women searching for a soulmate. We were all convinced finding a boyfriend was the missing piece of the puzzle to complete our lives.
“You need to fall in love with your life,” the dating guru told us. “Remember the dreams and passions you had when you were young.”
Casting my mind back, I recalled gazing into a travel agency by my university, mesmerised by their massive world map showing round-the-world flight routes. I promised myself: one day, I’ll do that. See the world.
But I never did. Real life took over - the relationship, the career ladder. All the things I was supposed to want. The timeline panic.
The guilt of ‘wasting’ your money
There’s an invisible hierarchy to how we’re supposed to spend our money. Saving up for a house deposit, a car or a wedding. Sensible investments. That’s responsible adulting.
What’s irresponsible? Booking a flight to Thailand for an adventure when you’re supposed to be hitting those milestones and getting your life sorted.
But that dream of exploring the world had reinserted itself into my brain and demanded attention. Surely taking my first ever trip to Asia had to be less mortifying than trying to chat up strangers in bars?
Solo travel can be really awkward
My destination was an island called Koh Chang at a place called Lonely Beach.
The irony of this name wasn’t lost on me. Especially when I arrived after a six-hour bus ride from Bangkok and found it fairly deserted.
That first evening, I sat in a local restaurant to eat a plate of Pad Thai. Hyper-aware of being on my own, I read the same page of my book 20 times and tried to project an air of “I’m having a marvellous time, thank you very much.”
For every traveller going solo by choice, for another it’s because they couldn’t find someone to go with. Staring at the empty seat opposite mine, my trip seemed less about empowerment and more about desperation.
I wondered if I’d made a huge mistake and would spend the whole two weeks talking to myself.
A woman approached me and asked if I was there alone. As I confirmed, I felt a wave of shame.
“Me too!” she replied with a smile. I hadn’t even noticed she was sitting by herself too. She asked if she could join me and we ended up talking for hours.
The next day, we went zip-lining over the jungle together. There’s an unflattering photo of me grimacing as I white-knuckle through the trees, just before I gave up.
Her confidence inspired me. Over the following days, I started approaching people and made more new friends. In the end, Lonely Beach wasn’t lonely at all.
Embracing our embarrassing moments
On my last day, we all went to the beach for the Loi Krathong festival of lights. As is customary in Thailand, we removed our shoes at the entrance to a bar. All night, we danced barefoot on the soft sand, celebrating under the stars.
When I returned to retrieve my sandals, I couldn’t find them in the mountain of footwear. Someone must have taken them by mistake.
Instead of worrying, I smiled as I walked barefoot along the road back to my accommodation. Here I was, halfway around the world, taking problems in my stride and doing just fine on my own.
Sometimes it’s the humiliating moments that become your most treasured stories.
The only thing worth caring about
Thailand marked the start of a love affair with solo travel. A few years later, I booked that round-the-world trip. Rather than focusing on a partner, I was finally making that younger version of me happy.
Maybe having a boyfriend isn’t embarrassing. And maybe travelling alone isn’t either. Whether you’re in a relationship or not isn’t the issue.
The only thing that’s actually awkward? Nearly missing out because you’re worried what other people will think. I would never have had these life-changing journeys without embracing the cringe.
So remember your dreams. Say yes to adventure. Do something that scares you. Lose your shoes and walk home barefoot.
Collect those embarrassing stories. Because in the end, that’s what really matters.
Claire — I adored this piece. You captured that exact alchemy of awkwardness and freedom that solo travel brings — the moment when you realize the empty seat beside you isn’t a symbol of lack, but of possibility.
I laughed at the image of you reading the same page twenty times (been there) and felt that quiet triumph in the barefoot walk home. Sometimes the most tender kind of courage is just showing up for ourselves — one flight, one meal, one wobbly zip-line at a time.
Here’s to losing more shoes and finding more of ourselves out there.
💛 Kelly
Oh, I loved this! There's something so beautiful about being vulnerable enough to embrace the cringe of a dating seminar and that being the catalyst to take the leap to start solo traveling and falling in love with it. it's so brave to go alone and you did it and are doing it! also, the little moments and interactions you get while solo traveling are so fun. going with friends (or with a partner I guess, no experience there) is also fun, but you don't meet as many people and just... stick in your bubble. and the part about reading the same page of a book twenty times and trying to seem like you were having a great time is so real. sometimes you just gotta pretend for a bit before it sticks lol.