Our journeys began when I leapt out of my comfort zone and into the comfort of an air-conditioned Mercedes van. For the first time in my life, I was abandoning my shoestring travelling ways and was to be whisked half-way around Sri Lanka by a private driver. Landing in Colombo the day before, I was welcomed with the familiar heady, humid intoxicating air that has always signalled my arrival at a tropical destination. But when Ranmal arrived at my hotel with his shiny white van, wearing a crisp white shirt and equally bright white smile, familiarity slipped away and I prepared myself for a two-week journey in unfamiliar luxury. Immediately, the difference between a private driver and a local tuk-tuk or taxi driver was clear. Ranmal was not so carefree with his chatter about local life - no complaining about the system, no sharing of fears about business being slow. Instead, he delivered short formal responses to basic getting-to-know-you questions and addressed me as ma’am. As we journeyed south towards Galle, I'm sure he observed some clear differences between his typical passengers and me. Did I want to visit a turtle sanctuary? No. Did I want to get my photo taken at a cinnamon plantation? No, not really. My responses were a reaction to the busloads of tourists and gift shops. Our prejudices were clear. He saw me as another souvenir obsessed, selfie collector. And I, having been scarred by underwhelming tours that a fueled by commission-based ‘recommendations’, saw him as a tourist-dollar chasing opportunist. We had a lot to learn about each other. On that first day, by the time he delivered me to the walled, fort city in Galle, we still hadn’t established much of a rapport. His training hadn't extended to passengers who are inclined to self explore and go with the flow. My life experience hadn’t prepared me for what felt uncomfortably like an employer/servant relationship. As I wandered through Galle that night, that uncomfortable feeling was magnified by my surrounds. Within the walled city, Portuguese and Dutch colonial architecture dominates, a step back in time that offers insight into Sri Lanka’s ruling past. Over the next week as we slowly progressed through the southern part of the country. Progress on our relationship was even slower. Too often Ranmal would pick me up in the morning and I would learn that he had been unable to find lodging close by. His usual clients tend to stay in fancy hotels that feature dedicated quarters for private drivers like him. But affordable rates go only to the drivers that bring wealthy tourists with them. With my choice to find my own cheap bed and breakfasts, I’d banished Ranmal to the city outskirts. I’ve always embraced public transport while travelling. Reading metro maps and picking bus routes shows me the lay of the land, navigating myself around a foreign place soon makes it not so foreign. On this trip, being chauffeured hundreds of kilometres a day robbed me of my bearings. I had to trust that Ranmal was guiding me to the places I wanted to be. Trust him I did. Know him I did not. Along our journey, I learned that whenever I heard a ringtone singing ‘Careless Whisper’ it was the sound of Ranmal’s wife calling. Why did George Michael’s lament about cheating regrets remind him of his wife? Was this a case of lost in translation? We didn’t know each other well enough to ask these questions. Just once, we did find connection. In Yala National Park, I invited Ranmal to join me on safari, on a quest to find a leopard. He’d driven many tourists to the park gates, but he’d never been in himself. As we jumped into a beaten-up old 70s jeep, his expression was the same as mine. Excitement. As we bounced along the pot-hole riddled dirt roads, our expressions were the same. Glee. As we stared down an angry bull elephant. Fear. And as we glimpsed the prized leopard. Awe. Shared experience over a two-week journey with another human would usually result in a life-long friendship. Sadly, as I farewelled Ranmal, I knew this would not be the story for us.