Not Just Service With a Smile, But a Signal

Personalization, Privacy, and the Design of Experience


A couple of years ago, I found myself in New York with an unexpected free evening. I was traveling alone, and on a whim, I checked for a last-minute table at a restaurant I’d long admired, one of those places known not just for its food, but for the way it made people feel.


To my surprise, I got in.


It was a beautiful setting. The service was warm and impeccable. The food and wine were as thoughtful as the lighting, the pacing, and the gentle rhythm of the whole experience. Hospitality at its finest.


Somewhere between my first glass of wine and the arrival of my appetizer, a server came by and struck up a conversation. They were friendly and professional. At first, I appreciated the attention. It can be nice to feel seen when dining alone. But then came an unexpected moment: they made a passing comment about my career in tech and my support for the LGBTQ community.


It caught me off guard.


There was no malice, no awkwardness in their tone. If anything, it was meant as a compliment. But I found myself smiling while my mind raced. How did they know that? I hadn’t mentioned it. I hadn’t spoken to anyone else in the room. As they walked away, I was left with a strange mix of feelings: flattered, confused, and (if I’m honest) a little uneasy.


This wasn’t a case of clumsy service. It was the opposite. Something in their system had worked exactly as intended. The question was whether I had intended it.


That moment came back to me while reading Nico Madrigal‑Yankowski’s SFGATE piece, Bay Area restaurants are vetting your social media before you even walk in. Some restaurants now use booking tools and social media to anticipate guests. The experience feels seamless, but it’s shaped by systems we rarely see.


There’s a quiet tension here.


When systems work well, they feel like magic.


When they work too well, they start to feel like surveillance.


Will Guidara’s Unreasonable Hospitality makes a beautiful case for overdelivering, not with extravagance but with care.


With humanity.


His stories of handwritten notes, favorite dishes remembered, coats retrieved without needing a number. These aren’t just about detail. They’re about designing systems that reflect how we want people to feel.


But even in Guidara’s world, intention matters more than information. There’s a difference between remembering and tracking. Between noticing and mining.


And it’s not just restaurants. In workplaces, apps, and airports, we’re surrounded by systems: processes, policies, rituals, and yes, sometimes technology, all meant to create ease and consistency.


Sometimes it’s seamless.


Other times, it’s jarring.


A personalized push notification. A chatbot that knows your birthday. A loyalty recognition moment that almost lands, but misses the mark.


The Bear, for all its anxiety and chaos, shows something similar from the inside out. The best moments of hospitality are hard-won. They come from care, ritual, repetition. They come from systems that are designed not just to function, but to feel. And when those systems crack, you see it immediately in the guest’s experience.


So what does it look like to design experiences that respect both privacy and presence? That remember without overreaching? That serve without assuming?


Maybe it starts with asking one simple question:


Are we building this to help someone feel known, or just to know more about them?


That small difference might be the real heart of hospitality, whether in restaurants, in tech, or in life.


I’d love to hear how you’ve experienced this, when it felt right, or when it crossed a line.

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