Rebecca Field Jager navigates into nostalgic and new territory on a road-trip romance. The question is: will she be happy she went or wish she’d steered clear.

We clink our shells together in a toast. Around us, swarms of revellers buzz about the Toronto restaurant party room, eating Canadian oysters and washing them down with Ontario VQA wines. In this moment, however, despite the din, there is just the two of us, our eyes locked knowingly. Actually, considering we only met a few months ago, I know this man quite well.

For starters, I know that beneath that tailored suit and cool demeanour, his heart is thumping at the thought of getting this gelatinous creature down.

As is mine.

Here’s to road trips, I murmur, referring to a journey we’d taken together early on in our relationship and during which he tasted oysters for the first time.

Road trips are the stuff of many our childhood memories. Back in the ’50s and ’60s, when most families owned at least one car and newly constructed highways crisscrossed the continent, parents everywhere loaded their kids into the back seat and took to the open road. So maybe it’s not surprising then, that mere weeks into our courtship, when we both discovered neither of us had ever been to Ontario’s newest appellation, Prince Edward County, we simultaneously bellowed, “Road trip!” And then, over glasses of wine and his laptop, plotted a three-day adventure.

Mind you, a few of my gal pals were surprised that I’d committed to such a lengthy haul with someone I hardly knew.

What if he’s a boar or, worse, a bore?

But as a single boomer in the throes of online dating, I don’t feel I need years to figure out whether a person is, or isn’t, the one. I know what I like and dislike, what will grow on me or drive me insane. And so I viewed the road trip, during which we’d travel together, eat together, sleep together, navigate and negotiate, like an all-encompassing immersive experience, a microcosm of what life with this person might be.

According to Ellen Starr, a Toronto-based couples counsellor, my assessment is not off the rails. Road trips, she attests, can be a great way for couples to explore newfound relationships. “The planning alone can serve as a litmus test, a road map to the future. Are both partners getting an equal say? How do you each handle compromise? How are responsibilities such as booking accommodations divided?”

She says, too, that longtime couples embarking on a new chapter in life — empty nesters, the newly retired — can benefit from the environment the interior of a vehicle on a lengthy journey creates. Unlike the popular convention of “pillow talk” with long, deep conversations in which a couple stares into each other’s eyes, interestingly, the fact that you’re not facing each other can be less intimidating.

“This is often true for men especially who traditionally drive, but women, too, might be more apt to be open when they can gaze out the window, looking away.”

Sure enough, during the two-and-a-half-hour trek from Toronto to PEC, Roameo — as I’d secretly dubbed him, get it? — and I fell into a candid conversation with me asking pointed questions and he pausing ostensibly to adjust the rear-view mirror or the air conditioning but more likely to collect his thoughts before answering. I fiddled with the lid of my water bottle or took a sudden interest in the scenery before spilling my guts about past angsts, future dreams.

By the time we pulled into Cribs on the Creek, a condo-style accommodation in downtown Wellington, we were both ready for some lighter conversation and excited to officially start our holiday.

If new relationships are all about chemistry and a road trip is a catalyst, then our lovely room was the petri dish in which a bit of him and a bit of me mixed together to see if we would fizzle, bond or explode. In the ensuing days, we learned a lot about each other from this co-habitation experiment from our levels of tidiness to our appetites for intimacy. But it was from our time out and about that we learned the most about who the other is.

Here’s the thing: up until now, like many new duos, we’d spent most of our time together in a bubble, tucked away in the corner of some restaurant or holed up in one another’s home alone, without the company and complexities of family or friends. Road trips give couples the chance to come up for air, to interact with other people and perhaps use these stories to steer their own conversations into deeper, unchartered waters.

Prince Edward County, a hotbed of entrepreneurship, is the perfect place to go story hunting. It is rife with risk-takers — hoteliers, restaurateurs, brewmasters, artisans and first-generation winemakers  most of them happy to share their tales if they have time.

As an entrepreneur myself, I’m always keen to hear a good roll-the-dice yarn and Roameo, a long-time corporate guy but with retirement and all its possibilities not far away, was too. And so, after our visits, we’d sit on one of the many patios that dot the region sipping wine or craft beer and marvelling at the boots-on-the-ground nature of folks like Sam Ravenda, who left her Toronto job in the hospitality business to open Sand and Pearl, a rustic seafood restaurant and oyster bar on the main strip in Picton. Or Dan and Lynn Sullivan, owners of Rosehall Run Winery, who described the thrill and terror of being among the first to plant in this stony soil. Or Sarah Sklash, who along with her best friend bought a roadside fishermen’s lodging, and turned it into The June Motel, a swanky, unapologetically pink, 1960s-esque oasis. Or Caroline Granger, owner of Grange of Prince Edward Winery, who took the family farm of her youth, planted 10 acres and grew it into 60 acres of lush vineyards, in which, by the way, we enjoyed a freshly prepared picnic. Roameo and I clinked our glasses together to all of them!

But it wasn’t all wine and roses.

In fact, perhaps our most telling moment came when we were driving away from one of these encounters on the last day of our journey. I was doing what I always do when I’ve enjoyed a holiday, fantasizing about moving to the destination, bubbling over with excitement of so many options. I could barely contain myself as I sat in the passenger seat going on and on about how cool it would be to open a business such as the one we’d left, to try something new.

But then, just when my enthusiasm was about to reach its most passionate peak, he asked me to bring up the calculator on my cellphone and input a series of numbers. How many customers was it reasonable to expect? How many months is the average season? What would the overall operational costs look like? By the end of the exercise, my heart had sunk into the floorboard.

You’re damn right I gazed out at the scenery. A deep breath, and then I turned to him. “Well, aren’t you a buzzkill?”

Much to my surprise, without so much as checking a mirror, he let out a knee-slapping, hearty laugh, and I couldn’t help but start laughing, too.

Oh sure, we may not ride off into the sunset together, I remember thinking, but we now know each other well enough to be ourselves in each other’s company, and that’s a trip in itself.

And it’s why, although we only date occasionally, I’ve invited him to this wine and oyster evening. “To road trips,” he says, and we bring the shells to our lips, smiling bravely. And then, down the hatch we go.