Have you ever sat at a restaurant and watched someone order the most expensive bottle of wine on the menu, only to realize they had no idea what they were drinking?

I’ll admit it. Back in my corporate days, I was that guy once or twice. Fresh out of a promotion, trying to impress a date, ordering things I couldn’t even pronounce properly because the price tag seemed to scream “success.”

The thing is, after spending eight years climbing from junior analyst to senior analyst, I learned that genuine wealth rarely announces itself. The truly affluent folks I worked with? They ordered what they actually wanted, not what would make the best impression.

These days, I can spot someone trying too hard to look wealthy from across a dining room. It’s not about judging anyone (we’ve all been there), but recognizing these patterns can save you from unnecessary financial stress and social awkwardness.

Let me walk you through the eight dead giveaways.

1. The most expensive wine without knowing anything about it

Nothing screams “trying too hard” quite like pointing at the priciest bottle and saying, “We’ll take that one.”

Real wine enthusiasts ask questions. They want to know about the vineyard, the year, what pairs well with their meal. They might even order a moderately priced bottle they genuinely enjoy over the $500 option.

I once watched a colleague order a $300 Bordeaux at a business dinner, then proceed to mix it with ice because it was “too warm.” The sommelier’s face was priceless. Meanwhile, our CEO ordered a $45 bottle he’d discovered on a trip to Oregon and spent ten minutes telling us why he loved it.

Guess which one looked more sophisticated?

2. Lobster when they clearly don’t like seafood

You can always tell when someone orders lobster just because it’s expensive. They’ll push it around their plate, drown it in butter, and leave half of it untouched.

I had a friend who did this religiously on first dates. He’d order the lobster tail, struggle through eating it, then complain about the “fishy smell” afterward. When I finally asked him why he kept ordering it, he admitted he thought it made him look successful.

People with actual money order what they want to eat. Period. They’re not performing for an audience.

3. Bottled water with names you can’t pronounce

Voss. Fiji. San Pellegrino. And then there’s that $20 bottle of “volcanic filtered artesian water” that tastes exactly like the filtered stuff from your kitchen tap.

During my bartending nights after leaving corporate, I watched countless people order exotic bottled water to impress their dining companions. The kicker? Half the time they’d leave it barely touched.

Warren Buffett famously drinks Cherry Coke. Mark Zuckerberg is known for his simple tastes. Actual wealthy people aren’t trying to prove anything with their H2O choices.

4. Caviar as an afterthought

“Oh, and add some caviar to that.”

If someone’s casually tacking on caviar to random dishes or ordering it without any real interest in eating it, they’re probably more interested in the Instagram post than the actual experience.

I’ve noticed that people who genuinely enjoy caviar know exactly how they want it served. They have preferences about the type, the accompaniments, the temperature. They don’t just order it to order it.

5. The “supplement” items nobody asked about

You know those menu items that say “market price” or require a supplement? Ordering multiple supplements just because they cost extra is a classic move.

“Add the truffle shavings. And the foie gras. Oh, and upgrade to the wagyu.”

I watched someone do this recently, turning a $30 pasta into a $95 monstrosity that completely destroyed the balance of the original dish. The chef probably died a little inside.

People comfortable with their wealth add supplements when they genuinely want them, not as a wealth display.

6. Multiple appetizers for a party of two

Ordering five appetizers for two people isn’t generous. It’s wasteful and obvious.

Back when I was optimizing for all the wrong metrics in my twenties (salary, title, those Instagram moments), I’d do this constantly. Order way too much food, barely touch it, all to create an image of abundance.

Now? I realize that thoughtful ordering shows more sophistication than excess ever could. Quality over quantity isn’t just a cliche.

7. The entire right side of the menu

Some people literally scan for the most expensive items and work backward from there. They don’t read descriptions. They read prices.

I once went to dinner with someone who proudly announced they “only order from the right side of the menu” (where the prices are). They ended up with a dish they were allergic to because they hadn’t bothered reading what was actually in it.

Genuinely wealthy people know that price doesn’t always equal quality. They’ve eaten at enough places to know that sometimes the $18 house special blows the $65 imported whatever out of the water.

8. Ordering “whatever the chef recommends” without caring what it is

This sounds sophisticated in theory, but when someone says this without any follow-up questions or genuine interest, it’s transparent.

“Just have the chef send out whatever’s most special tonight.”

Then they sit there, not knowing or caring what arrives, as long as the bill impresses whoever they’re with.

Compare this to someone who says, “I’m really in the mood for something light but flavorful. What does the chef recommend?” That’s someone who actually cares about their dining experience.

Rounding things off

Here’s what I’ve learned after years of watching this behavior (and, embarrassingly, participating in it myself): trying to look wealthy through restaurant orders is exhausting and expensive.

The irony is that the people you’re trying to impress can usually see right through it. And the ones who can’t? They’re probably not worth impressing anyway.

Real confidence comes from ordering what you genuinely want, whether that’s the house burger or the tasting menu. It comes from asking questions when you don’t know something instead of pretending expertise you don’t have.

These days, when I go out to eat, I order what sounds good to me. Sometimes that’s the special. Sometimes it’s the cheapest thing on the menu. And you know what? The meal tastes better when you’re not performing for an imaginary audience.

The next time you’re out, pay attention to the people who seem most comfortable in their own skin. They’re usually not the ones making a big show of their order. They’re the ones genuinely enjoying their meal, their company, and the experience itself.

That’s the real luxury.