Can you fall in love on a first date that lasts for two weeks?

Forget the Longest Third Date, let's try the longest first one and make it a road trip.

For years I’ve rotted my brain with reality dating shows, mainly for work but sometimes for fun. I’ve written about the concept of strangers meeting strangers and attempting to fall in love so often, through watching shows like Married At First Sight, The Bachelor, and Love Is Blind, maybe it was a natural progression I’d say yes to undertaking a holiday with a man I technically had not met in real life before.

Let me set the scene for you: it was a dating app match that happened in October 2023 with a couple of voice memos being exchanged on Bumble, but it wasn’t to be — he was heading back home to the UK after a trip to Australia and I, mildly traumatised from once falling in great lust with a British boy, was looking for someone who wasn’t leaving the country any time soon.

We stayed in touch, exchanging Instagram memes, chats, music recommendations, and eventually a friendship of sorts built along the way which took a turn around June or July 2024 — he had just exited a dating situation, and I had been on a series of highly questionable first dates that had left me depleted. I had just watched the Netflix documentary Longest Third Date — where two people went on their third date during the start of COVID and got stranded in Costa Rica for months — and we joked about going on a holiday in Thailand and saying a big old F U to the dating world and its traumas. Then a little while later, he told me he could book relatively cheap flights to Australia in October. I hadn’t had a holiday for some time, so I thought I was calling his bluff when I said I’d see him soon. Turns out he was calling mine too, because he actually booked the flights and we organised a two-week road trip together.

While we ramped up communication to an extent — FaceTimes, voice memos, etc. — it was a no-set expectations kind of deal. “Do you have any doubts about coming over here?” I asked him one night. “No,” he said. “But what if we did actually fall in love?”

It sounds like it should be the perfect modern-day dating story: boy and girl meet on app, communicate all their fears and desires from the safety of their phones, then decide ‘fuck it’ and embark on a wild road trip of Australia, where everyone wanted the ending to be the two people falling in love and realising the universe had brought them together in this wild and wonderful way.

So what’s it actually like to go on a first-date road trip?

For someone who’s a chronic overthinker, I weirdly wasn’t overthinking this situation, despite my worried friends adding me to Find My Friends and tracking my every move. I was never nervous about meeting him — we had established enough of a friendship for me to know we’d get along well enough.

We travelled super well together and spent pretty much every waking minute together for nearly three weeks. During the fast-tracked time period you go through a lot of stages — of course it’s fun and exciting to meet each other for the first time like any first date, but you don’t follow the same process of what it’s like to develop a crush… and that can be good and bad.

For example, part of the exciting and equally insufferable parts of early dating is figuring out if someone likes you or not — having the banter, having the first couple of dates, wondering when you’ll hear from them next, building up a yearning or longing for wanting to see them again. That’s taken away when you embark on a relatively crazy experience where you’re hanging out with one person for a solid amount of time. You not only completely skip that “exciting” period, you also skip the honeymoon period. For us, particularly, it was a fairly fast transition from strangers who finally met IRL to old married couple. We got along because we’re both relatively chill people, we made each other laugh (somewhat at each other, somewhat with), we belted out our joint playlist in long car trips down south and up north. But along the way as you forge a connection while spending every minute with someone, you forgo the romance.

On the other hand, one of the most annoying things about early-stage dating in the modern world is having no idea where you stand with someone. On the road trip, our communication had to be top-notch. We figured out very early on that we didn’t have that excitement in the pit of our stomachs that would lead to an overly passionate romantic connection. We were comfortable and we became good friends. As early as night three, we had a discussion about how we were feeling, both admitting to being bad at being vulnerable and letting our defences down. During week two, we cemented that while we were enjoying our time, we didn’t see it progressing in a romantic way that would have one of us desperately buying a plane ticket again any time soon. These conversations normally feel really hard and awkward in the modern dating world. In the context of a road trip, it was just a necessity with no ego or hurt feelings attached.

When a first date road trip becomes your most secure dating experience

In credit to both the situation and the person I was with, I realised after the road trip that the dating experience was probably the most secure connection I had experienced in my dating life. I’ve written numerous times of my ability to flip-flop between avoidant and anxious when it comes to dating, often accidentally mirroring the energy of the people I am with. Because our communication had to be strong, we navigated through typical friendship and dating problems with relative ease. It’s not to say there weren’t a few moments of tension or moments where we simply got sick of each other. But because we were never coming at it from a place of ego or even fear of getting hurt, we could just simply be ourselves…. the good, the bad, the insecure, the anxious, the avoidance, and everything in between.

One night, in a moment of tension I was ready to be properly mad at him about something that could have seemed fairly trivial, but there had been a build-up (disclaimer: it was about phone use). It was something he apologised and took accountability for straight away — and for me it was an amazing learning lesson. I had so often dated combative men who would pick fights or manipulate situations so much that I’d end up apologising for “reacting” to things they had done wrong. I realised I was still operating on a level where I was ready to shut myself down awaiting his responses to any form of conflict. When he calmly had a conversation with me and took accountability, I had to do a lot of work that I wasn’t expecting to adjust my own mood to get things back on track and not become the person who stays sour and silent for the rest of the night.

I had never had someone apologise so directly to me before and learn from the incident. I was always so ready, one foot out the door, to be proven right that I shouldn’t let myself get vulnerable or react to things, even if people were doing things to upset me regardless of whether it was unintentional. It was eye-opening in the sense of making me question if I’ve been on the path of a self-fulfilling prophecy that a lot of people pleasers fall trap to: if you never articulate your boundaries, what annoys you, and what your needs are and just expect people to read your mind, you’re also often going to approach vulnerable situations like dating and friendships by not showing up as your authentic self and get upset or resentful later when your untold needs or boundaries aren’t being met.

On my road trip I had no choice but to be my authentic self — including all of the parts of myself I usually want to hide. Whether it was insecurities around when my PCOS flares up my skin (which is did smack-bang in the middle of this trip) to recognising and verbalising my own needs about being able to have solitude and alone time instead of feeling guilt that I need to be someone’s everything at all times. Through being in this wild experiment and having to navigate things as openly and honestly as we could, I realised I had probably just experienced my first, proper, secure dating experience.

Battling and beating the ick

A lot of issues when first dating too is experiencing the “ick” or finding out those little quirks or parts of people you have fantasised about and finding it hard to come back from. Some icks are real and may be a problem for longterm compatibility — e.g. politics and values — while others may be trivial and harsh — e.g. watching someone trip over (which he watched me do at least three times).

Because of the nature of our experience and knowing we were only seeing each other for around four weeks (two weeks being that road trip, the other time being split between his travels and hanging out) if we found icks with each other, we simply just… had to get over it. Sure, we talked about some things — our politics weren’t exactly aligned and neither were our future plans — but it came from a place of interest and learning vs. a place of bitter disappointment because the person you’ve accidentally put on a pedestal isn’t adhering to your expectations.

We didn’t find love, but we found something important

In conclusion, sorry to burst everyone’s rom-com dreams but we didn’t fall in love. There’s love and good vibes and good memories, but not that elusive spark.

But I think what we experienced was just as important. We experienced what it was like to accept someone wholeheartedly as their true, authentic self without trying to change them to fit your own needs or expectations of what you’re looking for in someone.

And that may be the most important life lesson I’ve learned when it comes to dating so far.