When I Turned 30, I went to a Couples' Resort...Alone
This was the start of my writing journey
I started my full-time freelancing career at 30. I freelanced here and there before, mostly writing short blogs and listicles, and eventually landed at a local magazine in Toronto where I stayed for a couple years. But I’m antsy. I don’t like to stay in the same place for too long. I didn’t know it at the time but I was a born solopreneur.
Speaking of solo…I went on my first solo vacation a month before I turned 30. To the Bahamas. At a couples’ resort. Okay, maybe technically it wasn’t a couples’ resort but there were couples pretty much everywhere, and then there was me.
Just chilling. Alone.
It was an unusual and unique experience to say the least. I didn’t know it at the time but it became the story that kicked off my freelancing career. It was the first time I looked at my life as a sort of inspirational experiment that could be shared through my writing. It was the first time I thought my experiences were worth sharing through my writing. It was the first time I thought I had something special to say — and I knew the more embarrassing relatable the story, the better.
I sold the pitch about my trip to Nerve (RIP). It was my first essay published as a freelance writer and I never looked back.
Soon I realized there was a niche in the relationship space, and I wanted to explore it as a single woman. I was fascinated with what I could discover about myself while writing about dating and relationships and being single…and how that might translate into a story for readers.
Now I am writing a book proposal for a book of personal essays, essentially doing the same — sharing more embarrassing relatable stories about being single.
Below is a preview of the essay about traveling alone to the Bahamas to a couples’ resort. Alone. Enjoy at my expense.
P.S. this is the sort of content you will get with my PAID subscription.
“You here with a boyfriend?” the taxi driver asked me as we whirled through the winding roads of Nassau, passing million dollar views of turquoise waters, towering palm trees, and white sand beaches – in other words, paradise.
“No boyfriend. Just me,” I said, which I immediately regretted. One, because he could’ve been a serial killer, and two, because telling people you had a one-way ticket to paradise was often considered brave and exciting, but a one person ticket to paradise? That was just sad and pathetic.
“Why you here alone? Pretty girl like you should have a boyfriend.”
Aside from the “pretty girl” part, it was the type of comment I didn’t love. I was just a month shy of my 30th birthday, and I was quickly discovering my life was now a to-do list of “shoulds.” You should buy a house, you should eat more quinoa, you should train for a marathon (why were all thirtysomethings suddenly obsessed with running?). From my Facebook feed to the nosy neighbor on my parents’ street to the flashy women’s magazines on the back of my toilet, I couldn’t escape the shoulds. And marriage? Well, that was a given. Especially as a woman. An unmarried woman at thirty was a crime against humanity. After all, what about the ticking time bomb in your uterus? If you weren’t married, or at least dating someone with marriage potential, then poof! you were sentenced to something worse than death: a life in which you completely disappear from the social radar, or become so unrecognizable that no one would want to sleep with you, let alone marry you.
If 30 was the age where we graduated into official adulthood of engagement announcements and wedding invitations – or baby showers, if you were really an overachiever – my love life read like a remedial student’s report card. Other than an awkward situationship with an actor who starred in one of my plays the year before and a handful of online dates that went nowhere, I had no romantic life to speak of. It’s not that I didn’t want to “graduate” with my fellow cohorts into a cozy life of binge-cheating and scheduled Friday night sex, but I also wasn’t the sort of person who wanted to drag my butt to summer school in order to play catch up. I didn’t want to date for the sake of dating.
“Maybe next time you come, you bring a boyfriend,” the taxi driver said to me.
That seemed to be the consensus lately. Only a few weeks earlier, over a bottle of wine, my roommate had exclaimed to me: “We need to get boyfriends!” Her tone, both matter-of-fact and urgent, as if she was reminding me we needed to get toilet paper – put it on the top of the list or live in regret or at the very least incredibly inconvenienced.
“But why do we need to?” I wanted to ask. Months earlier, when a friend reminded me that dating online was like “taking on a second job,” I promptly deleted my profile. The ROI wasn’t enough for me. Scrolling through endless photos of group shots and mirror selfies and unsolicited dick pics just for that rare diamond of a guy who would at least ask your name first before sending a photo of his schlong and a “U up?” No thanks. I wasn’t trying to be a contrarian, I was just tired. Tired of analyzing the text messages, tired of going out on first dates with men who insist on showing you their foosball table right away (a euphemism if there ever was one), and I was especially tired of thinking I needed to have a man to feel like I was complete. I was happy being single. I was happy hanging out with my friends, sleeping in the middle of the bed, being free to do what I wanted when I wanted to, and not having to compromise on, well, anything. It’s not that I didn’t want a relationship, eventually. I just figured there was enough time to experience more when it felt right to me.
So, in anticipation of my third decade, I decided to do something I thought was far more liberating than deciphering mortgage interest rates or suffering from runner’s diarrhea – I chose to travel solo for the first time. No one could accuse me of playing it safe or being less of a grown up when I blew out the candles on my 30th. As far as I was concerned, thanks to my one person ticket to the Bahamas, I had nothing left to prove.
Then my taxi driver pulled up to the resort, and suddenly “should” hit the fan. Past the outdoor hanging fans and potted palm trees, there were couples as far as the eye could see. The Couple Holding Hands While Strolling the Gardens In High Waisted Shorts. The Couple Pinching Each Other’s Butts on The Tennis Courts. The Couple Drunk Making Out at the Pool Bar. Couples here, couples there, couples everywhere.
Yes, it appeared I was staying at a couples’ resort. Alone.
In all fairness to me, I didn’t know it was a couple’s resort when I booked the trip. And in all fairness to the resort, it didn’t advertise itself as one. In fact it was rated as more of a hot spot for college kids for spring break and graduation celebrations. It was November; I assumed I would miss out on feeling like an outsider among the stampede of raging hormones and codependency. But as one friend put it to me later that night: “You went to the Bahamas alone. What did you expect?”
Not this.
