While these well-meaning comments might sound supportive to the Boomers saying them, servers hear something entirely different, and after a decade in luxury hospitality, I've collected enough of these "compliments" to fill a very awkward book.
Look, I still remember the exact moment I realized that not all compliments are created equal.
I was working a dinner shift at this high-end steakhouse in Manhattan, probably my third year in fine dining. This older gentleman, dressed impeccably in a three-piece suit, called me over after I'd served his table their appetizers. He looked me straight in the eye, smiled warmly, and said, "You're doing such a good job, young man. You should be really proud of yourself."
On paper, that sounds nice, right? But something about the way he said it, like he was patting a golden retriever on the head, made my skin crawl. My colleague later told me she'd gotten the same treatment from him, except he'd added, "You're so articulate for a waitress."
After over a decade in luxury hospitality, from boutique hotels to serving ultra-wealthy families at resorts, I've collected quite the anthology of these backhanded "compliments." And here's what I've noticed: there's a particular generation that seems to have mastered the art of the condescending compliment without even realizing it.
Before we dive in, let me be clear. Most people who say these things genuinely mean well. They're trying to be kind. But intent and impact are two very different things, and understanding the gap between them might just save you from that awkward moment when your server's smile becomes a little too forced.
1. "You're too smart to be doing this job"
This one's a classic. I heard it at least once a week during my years in restaurants.
The person saying it thinks they're giving you a massive compliment. They're acknowledging your intelligence! They see your potential! But what they're actually saying is that service work is beneath intelligent people. That waiting tables is somehow a consolation prize for those who couldn't make it in the "real world."
Here's what they don't know: I once served alongside a guy with a master's degree in engineering who was taking a gap year. Another colleague was putting herself through medical school.
And me? I was making more money than most of my college buddies who'd gone straight into corporate jobs, all while learning about wine, food, and human psychology in ways you can't get from a textbook.
The restaurant industry attracts all kinds of people for all kinds of reasons. Some are building careers in hospitality. Others are funding their dreams. Many just genuinely love the work. None of them need strangers evaluating whether they're "too good" for their chosen profession.
2. "You must be working here to put yourself through college"
Similar energy, different flavor. This assumes that restaurant work is merely a stepping stone, never a destination.
I've watched servers in their 40s and 50s, who've made conscious choices to stay in the industry, receive this comment with barely concealed irritation. They're professionals who've honed their craft over decades, not kids killing time until their "real" life begins.
When someone drops this line, they're essentially saying, "I can't imagine you actually choosing this." It dismisses the entire hospitality profession as something people only do when they have no other options. Trust me, after seeing what some servers pull in during a good month at high-end establishments, plenty of them have options. They choose this.
3. "You're so articulate"
This one's particularly cringeworthy because it reveals such low expectations. What exactly were you expecting? Grunts and pointing?
During my time at a boutique hotel, I watched a colleague who spoke four languages fluently receive this "compliment" from a guest who seemed genuinely shocked that someone bringing him coffee could form complete sentences. The subtext is clear: I didn't expect someone in your position to speak well.
Servers are communicators by trade. They explain complex dishes, recommend wine pairings, manage difficult situations diplomatically, and often do it all in multiple languages. Being articulate isn't exceptional in this field. It's the bare minimum.
4. "Good for you for having a job"
I kid you not, I've heard this one multiple times. Usually delivered with the same tone you'd use to congratulate a toddler for using the potty.
What makes this particularly galling is that it assumes the server was somehow at risk of not having employment. Like showing up to work and performing a skilled job is an achievement worth noting, rather than what millions of professionals do every single day.
The condescension drips from every word. Would you say this to your accountant? Your doctor? Then why say it to your server?
5. "You have such a great attitude for someone in your position"
Ah yes, because clearly anyone in the service industry should be miserable, right?
This comment assumes that hospitality work is inherently degrading or depressing. That maintaining professionalism and friendliness while serving others requires some superhuman effort or tragic acceptance of one's lot in life.
During my years in Bangkok, where I spent time on the other side of the service equation, I noticed how different cultures view hospitality work. In many places, it's seen as an art form, a respected profession. Only in certain contexts does it become something people think requires a "great attitude" to tolerate.
6. "You're going places"
Going where, exactly? Maybe they're already exactly where they want to be.
This future-focused "compliment" implies that the server's current position is just a waystation to somewhere better. It's the verbal equivalent of patting someone on the head while looking over their shoulder for someone more important.
One of my mentors in the industry, a career server who'd been at the same restaurant for 15 years, had the perfect response to this: "I've already been places. This is where I choose to be now."
7. "You could be a model/actor/anything else"
Finally, we have the "compliment" that suggests the server's looks or personality are somehow wasted on their current profession.
Setting aside how inappropriate it is to comment on your server's appearance, this statement implies that hospitality is where dreams go to die. That surely anyone with other options would choose them over this.
The irony? During my time in New York, I knew plenty of servers who were models, actors, artists, and entrepreneurs. They weren't waiting tables instead of pursuing their dreams.
They were doing both, or had consciously chosen service work because it offered them something their other pursuits didn't: flexibility, immediate income, human connection, or simply job satisfaction.
Final thoughts
Here's what I learned after all those years in hospitality: the best compliment you can give your server is to treat them like the professional they are.
Thank them specifically for what they did well. "You gave excellent wine recommendations" beats "You're too smart for this job" every time. "I appreciate your patience with our large group" trumps "Good for you for working."
If you recognize yourself in any of these examples, don't beat yourself up. We all have blind spots, and generational differences in communication styles are real. The point isn't to make anyone feel bad. It's to help us all communicate better.
Remember, respect doesn't require mental gymnastics or backhanded observations about someone's potential. Sometimes the best compliment is simply treating someone like they're exactly where they belong.
