When my relationship unraveled nearly two years ago, I decided to suspend my career as an actuary in Boston and take a long vacation in Costa Rica, where I planned to learn how to surf and do yoga. Yes, it was the most clichéd response possible for a heartbroken 32-year-old Westerner like me.

After four weeks there, I was traveling by car with several friends I had met at surf school when we came upon a red-faced, middle-aged woman hitchhiking on the outskirts of a small village. Our radio was broken and we were bored, so one woman in our group, Abby, said: “We’ll offer you a ride on two conditions. First, you must sing us a song, and then you have to tell us a story. Do you accept?”

The hitchhiker, an American, responded with a crooked smile and a nod, freeing her hair from behind a Disney visor. “What would you like me to sing?” she asked.

“Anything you like,” I told her, “as long as it’s by Rod Stewart.”

One rendition of “Maggie May” later, her story began.

“It’s interesting you ask me to tell you a story,” she said, “because I’m living in the middle of a love story right now. I came to Costa Rica one year ago and met the man of my dreams. He was selling jewelry at a stand in the market. He’s Italian, and as soon as I spoke to him I felt something I hadn’t felt in my whole life. It overtook me. Love like in the movies, but this was real.”

This was promising.

“So you’re here to see him?” one of my companions asked.

“Yes, absolutely, dear. I’m heading into town now to see him for the first time in 12 months.”

We broke into huge grins; we too were now characters in her story, deliverers of love from a dusty roadside to the man of her dreams.

“Does he feel the same way?” Abby asked.

“Yes, he emails me every day to tell me so.”

I turned to her. “Are you excited to see him?”

“I haven’t thought about anything else for an entire year.”

“So you came all this way alone to see him?” I asked.

“Well, I had to, didn’t I? It was breaking my heart to be away from him.” She paused for a breath. “Although my husband came too; he’s back at the house.”

Our hands shot up with questions.

After my trip, I was eating steak at a Boston bar, still mourning that the woman I thought I would marry, Alejandra, had broken up with me. I’d met her five years earlier, and she was, in every way imaginable, an inspiration to me. She was the woman who taught me about love.

Next to me at the bar was a couple on their first date. I could tell because their conversation reminded me of those awkward exchanges you have with co-workers’ spouses at Christmas parties. They opened with a discussion about their commutes to the bar. They both lived within a 10-minute bus ride, and they managed to stretch out this topic for 30 minutes.

Next up, the weather: In Boston it rains sometimes, and they had both noticed this. An hour in, they turned to the really deep stuff. One was a teacher, and the other knew a teacher. How could they be destined for anything other than true love?

O.K., so I may have been directing some of my brokenhearted anger at them, but all I could think was that I wanted no part of this game. If being single meant having to partake in this kind of conversation, I’d rather pass. How could I go from the deep connection I had with Alejandra to discussing bus schedules and weather patterns?

I thought back to a dusty roadside in Costa Rica and the woman who shared her heart with four strangers. Why couldn’t we all embrace her openness? Why did being with a stranger so often mean we couldn’t immediately talk about meaningful things?

With this in mind, I decided to approach my re-entry to dating with a no-small-talk policy. Not that I would insist we talk only about heartfelt subjects; ideally, there would also be plenty of flirtatious joking and witty banter. I simply wanted to eliminate the dull droning on about facts and figures — whether it’s snowing or raining, how cold it is, what we do for work, how long it takes to get to work, where we went to school — all those things that we think we have to talk about with someone new but that tell us little about who the person really is.

Why can’t we replace small talk with big talk and ask each other profound questions right from the start? Replace mindless chatter about commuting times with a conversation about our weightiest beliefs and most potent fears? Questions that reveal who we are and where we want to go?

Admittedly, there were some issues with this policy, as my friends were more than happy to point out. They argued that some are not comfortable jumping directly into big talk, reasoning that certain people find small talk relaxing.

This is undoubtedly true. But another friend countered: “If she isn’t comfortable with it, then she probably isn’t right for you anyway. Your plan is a great way to filter.”

This friend operates his own bizarre filtering system by bringing women coconuts on first dates, claiming that any woman who doesn’t accept the coconut isn’t marriage material. Why? I have no idea. Even so, I accepted his opinion for what it was.

Another common complaint: You can’t ask big questions until you know the answers to the small ones; you need facts to know where to dig deeper. I’d argue, however, that you can elevate any question from small talk to big talk with a little tweaking.

One of the common questions I find myself asking a woman on a first date is where she has traveled. The response can quickly become a list of places, and once again we’re in résumé territory. So instead I’d ask, “What place most inspired you and why?”

Rather than ask about her job, I would ask, “What work are you passionate about?”

I wouldn’t ask about her longest relationship, as if length equals depth. Instead, I’d ask, “What’s the most in love you’ve ever felt?”

My first chance to put this new strategy into practice came with a woman I met at a party a few weeks later. She laughed when I explained my theory on big talk versus small talk and agreed to be the guinea pig.

She was moving away the next week, so we both knew we’d have only this one date, but we pledged to do all we could to avoid small talk. That night, we talked big and we talked deep. I learned about her brother’s drug problem, about the ex she had left years before and about the feelings she still had for him.

But we also joked about things both silly and shallow, managing to convince strangers that we had met in a fairground bumper-car accident, and recoiling in mock fright from a meal that was still wiggling on our plates. We laughed and we cried, and we learned nothing that would go on a résumé. Later, we kissed.

Since then, staying away from small talk has brought me one positive experience after another. Every date has turned into a real connection, or at worst, a funny story. All it takes is a willingness to dive into conversations that may make us uncomfortable or that many believe to be inappropriate for first encounters. After a while, though, it becomes natural to skip the facts and instead seek out our deepest thoughts and feelings.

My life moved on. I dated, traveled and started a new job. After a month of work, I went on a business trip with a new colleague. On the first night away, I found myself engaging in one of those dull work conversations people use to fill the time. My colleague was telling me the basics of his schooling, family and home.

“So how long does it take you to get to the office?” I heard myself ask. Then I stopped in horror.

I remembered the dusty hitchhiker in Costa Rica, the dates and the meaningful connections I’d made by escaping small talk. Even though my colleague and I weren’t on a date, we would still be spending a lot of time together in the foreseeable future, on business trips both short and long.

I took a deep breath and asked, “Why did you fall in love with your wife?”

He looked at me oddly, thought about it for a moment and then told me something beautiful.