Life doesn’t always give us a free pass. But it does hand out boarding passes. And sometimes getting the aisle seat can change your flight plan forever.

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That’s hardly what I was thinking as I raced up and down escalators and through security checks at Heathrow, trying to make a tight connection between a late-arriving overnight flight from Bangkok and an early morning hop from London to Lisbon. Fortunately, I made it – though my luggage didn’t – but this would turn out to be fortuitous as well. Already red-eyed and econo-class wrinkled, I could not have looked or felt less prepared for the ultimate stroke of pre-booked serendipity.

I could not have looked or felt less prepared for the ultimate stroke of pre-booked serendipity.

In my too many years as a frequent flyer, I had rarely struck up a decent conversation – let alone lasting relations – with anyone assigned to either cramped side of me. Most fellow passengers stuck sullenly to their headphones or shuffled through sales reports, reducing the odds of Cupid playing travel agent to those of a fatal crash.

This trip to Europe was no less miraculous – the result of an offer to help a friend’s Irish acquaintance in London revise a memoir of his hardscrabble childhood. And what divine matchmaker had moved me to add a brief detour to Portugal to celebrate the birthday of an old friend barely seen in a decade, the cost defrayed by writing an equally impromptu 24 Hours in Lisbon guide for Time magazine? Yet all this was topped in unlikelihood by the fact that the woman squirming uncomfortably in the middle seat next to me had just been inexplicably separated from her accompanying party by computer error.

Settling into my aisle seat and involuntarily gazing leftwards toward the porthole view of the tarmac, I glimpsed instead a shaggy wave of dark, strokeable hair, a lovely smile and an elegant profile, half-Grecian and half-Moorish Arabesque, that for some reason made me instantly blurt out the thoroughly unsubtle opener: “Are you Portuguese?”

Her affirmative answer allowed me to nervously show off my long, if somewhat distant, association with all things Portuguese. For the first time, it seemed, I could put to good conversational use my love for the shushing vowels of the language that animated Brazilian music, a subject I had researched for a book; or my enchantment with the Baroque architecture and incongruous echoes of Latin ease found in Macau and Malacca. I had even been to Lisbon once before, for the wedding of the Angola-bred buddy I was returning to see. Did one coupling prefigure another?

Our high-altitude small talk seemed to speed the flight as fast as any jets.

My comely row-mate and I were soon off to the referential races, comparing notes on a remarkable checklist of interests we seemed to have in common. Did I not share her passion for bacalhau, the salted cod that is close to every Portuguese heart? Was she a fan of Brazilian singer-poet Chico Buarque? And could it be that we both adored painter Francis Bacon and London’s Tate Modern? After all, she turned out to be a pedigreed art historian.

When she introduced herself with a decidedly un-Portuguese surname, I deduced she was already married – and this relieved me of any further pressure to make an impression in the pressurised cabin. Yet our high-altitude small talk seemed to speed the flight as fast as any jets. For a nervous traveller who usually counts down the minutes of potential turbulence, I couldn’t believe how quickly we descended for landing.

Still, our liaison might have ended right there had I not needed to wait for my missing bag on an ancient carousel in Lisbon’s quaint pre-EU terminal. This gave the woman, who went by the strangely un-Iberian moniker of Sandra, enough time to rush up and slip me her hastily scrawled phone number, even in the presence of the male companion with whom she had been reunited.

That Lisbon is one of the world’s most romantic cities is surely a world-class understatement. Or would Sheboygan, Ohio, have qualified under the circumstances? Surely, the mood of our first dreamy meetings was amplified by the plaintive wafting of fado ballads; the quaint trams plunging down to the sun-dappled blue of the Tejo River; the azure tile facades on the houses that made me feel as if I was wandering inside an enormous Alice in Wonderland teacup; the shaded plazasand strong cafezinhos (espresso shots) sipped beside open-air, Art Nouveau cafes in every park.

Our accidental affair started out at a decidedly Mediterranean pace.

Still, our accidental affair started out at an excruciatingly leisurely and decidedly Mediterranean pace. Day after day I left phone messages for Sandra. But whether she was genuinely busy or playing hard to get, it took until Wednesday, the fourth evening of my precious week’s sojourn, to arrange a rendezvous. In the meantime, I finished my 24 Hours in Lisbon research based on one morning’s guidance from a stodgy, elderly British expat – a slight that to this day my beloved has not forgiven.

Calming my nerves with sips of a lusciously thick Madeira wine, I waited for this intriguing stranger 25 years my junior at a rooftop bar suggested by my old friend for its sunset views over the historic jumble of orange-tiled roofs. But that night, she insisted on bringing her same male friend to chaperone our dinner at an Italian restaurant whose chef personally catered to her vegan priorities. Still, there was reason for hope: I learned that evening that Sandra was a rescuer of stray animals – might she be a rescuer of stray men too?

During Thursday's frenetic tour of Sandra’s favourite places, from an abandoned palace that housed an enormous horde of antiques she helped appraise, to the homemade soap shops and over-sweetened pastry spots lovingly visited by nostalgic neighbourhood grandmothers, we learned the most crucial bit of biography we held in common: both of us were at the tail end of interminable divorces that had left us less bitter than anxious to get it right the next time.

Later, she told me that I first entered her heart for the clumsy way I fumbled to zip and unzip a backpack that kept slipping onto the cobbled streets. I know she entered mine with the flimsy blouse whose straps also kept slipping – to reveal sweetly speckled shoulders. As the sunny day waned, she insisted we board a ferry to the far side of the Tejo – her secret bonus to our 24 hours in Lisbon. As commuters went one way and we went another, we seemed amazingly alone, the only people on Earth, taking the riverfront path along half-abandoned docks and warehouses that dead-ended at a tiny bar appropriately named Ponto Final.

Could any male suitor have ever been handed a more perfect setting for a first kiss?

It was all too postcard pretty, the one table set beside the water just for us, where we sipped wine and tentatively held hands, staring out at the panorama of Lisbon’s undulating spires and white hills that also seemed laid out just for us. Could any male suitor have ever been handed a more perfect setting for a first kiss? But of course, the very perfection gave me excuse to hesitate, lest one awkward moment ruin it all.

By Friday, with the clock ticking down on my allotted time in Lisbon, the unthinkable became the inevitable. I had to make my move. Besides, my lovely Lisboeta hostess had again made it easy by leading me to the Jardim das Amoreiras (Garden of the Blackberry Trees), a hushed, oblong refuge bordered by the stone stanchions of the city’s ancient aqueduct. She wanted me visit her favourite bastion of art and one of Portugal’s more obscure and untraditional museums, the Fundacao Arpad Szenes-Vieira da Silva. This small, ancient exhibition space was dedicated to displaying the life works of a Hungarian and a Portuguese painter – early 20th Century bohemians who had married and harmoniously created together, easel-to-easel, till death did their art part.

This hint of what she wanted for us was too obvious for me to ignore. Standing in the elm-shaded pathway to another cafe and another glass of port, I finally coaxed her to huddle close and soon found that not only was the kiss delectable, but, more importantly, my new friend showed no shame at all at being seen smooching in public with a grey-haired and grey-bearded gent.

With that confirmation of a need to rearrange our life itineraries, we had to rush to the airport – this time to see if the ticket for my Portuguese excursion could be extended. The news at the British Airways counter wasn’t good: no seats in the coming days, no changes allowed. But just as we were dejectedly crossing the lobby, both silently calculating how many tickets we’d be willing to tear up for another precious day or two together, the airline rep ran up to us with the good news that he had found a way to rearrange my reservation.

Once more, the vagaries of fate and fare basis rules seemed to be on our side, granting us just enough extra, wine-laden moments to plot future travel commitments together. We immediately celebrated with a dinner at a small, traditional haunt in the Bairro Alto, where Sandra insisted I try her favourite rendition of bacalhau a bras (salted cod with a comfortingly soggy, eggy treatment). For a Portuguese woman, nothing could possibly be more intimately inviting than the revelation of her favourite form of salted fish. In addition, she also invited me to address her from now on as Kika, her affectionate childhood nickname.

Are there really some destinations waiting for us all along?

Without going into the steamy details, I can say that no man has ever been treated to so wondrous a bit of sightseeing as the panorama from the little-known hotel to one side of a particularly memorable miradouro (viewing point), as my new partner pulled back the curtains to let in our first “morning after”. At that moment, the whole world seemed luminous, as though lit from within, the whitewashed welter of back alleys, the monasteries and castle ramparts and Atlantic beyond, all pulsating with that insistent half-Mediterranean, half-Saharan sun that had long ago inspired the Romans to name this land Lusitania (Land of Light).

What if Lisbon had not beckoned me? Or what if I had missed that connection in London, or the two of us had remained a row apart, mere backs of heads on sanitized rests? Suppose we had both planned journeys on another day, to another place? Or are there really some destinations waiting for us all along, that travel to us as much as we travel to them?

Two years later, Kika and I said our vows beside the central fountain of the Jardim das Amoreiras, the scene of our first kiss. And soon after, my new co-passenger gave birth to a little bundle requiring her very own bulkhead bassinette. Joana Francesca Liberdade we decided to call her – though given the circumstances of her progeny, we really ought to have chosen something with the initials BA.

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