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Create Moments that Earn Memories: Lessons from a 1st Date

By  Douglas Q. Warner

Nineteen years ago, I was a young guy finding my footing in adulthood, newly immersed in the hospitality industry, and trying to figure out what mattered most. One thing was certain: I had an amazing best friend, Jen. We had been inseparable through college, always in sync, always laughing, always that little whisper of “what if” lingering between us. But life, timing, and maybe a bit of obliviousness kept us in the safe lane of friendship—until one day, something shifted.

It hit me like a lightning bolt. What if I had been missing it all along?

So I did what any guy in his early 20s, fueled by nerves and newfound clarity, would do—I asked Jen out. Not for a casual drink, not for just another hangout. This time, it was different. This time, it was a date.

And not just any date—a Valentine’s Day date.

I chose Carlo’s Cucina, a tiny, bustling Italian spot in our neighborhood in Allston, Massachusetts. It wasn’t flashy or expensive, but it had soul. The kind of place where the pasta is always fresh, the servers have personality, and the walls feel like they’ve soaked up decades of laughter and love stories.

I remember every detail. The nervous energy before I picked her up. The flowers I handed her, hoping it was just the right mix of thoughtful and not-too-much. The way we grabbed a drink beforehand to shake off the jitters, settling into something that felt effortless. The way the restaurant was packed, the tables squeezed so tightly together that every conversation blended into a hum of warmth and connection. The way I pulled out her chair—not because I thought I had to, but because I wanted her to feel special.

The food was perfect. The wine flowed. Our server was charming and knew exactly how to read the room, playing along with our excitement and making the night feel even more like it was meant to be.

That night changed everything.

Fast forward to today, and Jen is my wife of 12+ years, the mother of our two amazing daughters (and yes, our beloved dog, Otto). That first date—the night we finally got it right—is now part of our family’s story, the foundation of a life I can’t imagine any other way. And every Valentine’s Day since, I’ve never taken it for granted. I still ask Jen to be my Valentine, and for 19 years straight, she’s said yes.

We even go back to Carlo’s. Because some places hold more than just memories. They hold meaning.

Why This Matters to Us

The truth is, we all have the power to create moments like this for someone else. This is what hospitality is all about.

Every night, couples step into our venue, their energy crackling with the same anticipation I felt back then. First dates, anniversaries, celebrations of love—these moments aren’t just another reservation on the books. For them, this could be the night they look back on decades later, remembering the exact meal, the exact laugh, the exact way they felt seen.

And that’s where we come in.

At Your 3rd Spot, we don’t just offer food, drinks, and games. We create the backdrop for stories people will carry with them forever. We give them something to come back to—not just because they had fun, but because they felt something.

This isn’t about executing another busy service or checking boxes on a shift list. It’s about understanding that when a couple walks through our doors, we have the privilege of setting the stage for a moment they might never forget.

So Here’s My Ask

As we gear up for Valentine’s Day, I want all of us to take this responsibility seriously. Let’s go beyond great service—let’s elevate the experience. Let’s ensure every touchpoint, from the moment they walk in to the moment they leave, is intentional.

That means:

  • Using second-order thinking to anticipate their needs before they even realize them.
  • Leaning into predecision and priming to create an atmosphere where they can relax, connect, and be fully present.
  • Making sure every detail is designed for seamless execution, so nothing interrupts the magic of the night.
  • And most of all, making people feel seen. Because when someone feels seen, they come back. Not just to the space—but to the feeling.

Lessons from a First Date

  • Every night, we have the opportunity to be part of someone’s story. What kind of story are we helping them write?
  • The power of firsts. People will always remember their first time doing something—whether it’s their first visit to us or their first date with someone they might marry.
  • Value the two-top. A single couple sitting at a table might not feel as exciting as a big event buyout, but here’s the truth: a two-top, treated the right way, will be back. Again and again. They will celebrate anniversaries, birthdays, and milestones with us. And they will tell their friends.

Jen and I will never forget that first date 19 years ago. Let’s make sure that the couples who spend their first dates, anniversaries, and Valentine’s Day with us this year never forget theirs either.

February 3, 2025

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