By Marco Shalma.

You never find out your friend is an embarrassing tipper when the check hits the table. That’s rookie thinking. By then the damage is already done, the server has clocked it, and you’re quietly opening Venmo like you’re paying hush money. In New York, tipping isn’t etiquette. It’s a personality trait. And the signs show up early.

The first red flag is how they talk about money before food is even mentioned. If they say “I’m not cheap, but…” congratulations, you’re dining with someone who absolutely is. People who tip well don’t pre-negotiate generosity. They don’t warm you up for disappointment. They don’t need to explain themselves. They just show up and handle it.

Then comes menu behavior. Watch closely. The embarrassing tipper treats prices like a personal attack. They complain about portions before the plate lands. They ask if sides are “necessary.” They start doing mental math out loud. Anyone calculating this hard before ordering is already subtracting from the tip.

Listen to how they talk about service. This one is deadly accurate. If they say things like “it’s literally their job” or “I tip based on effort,” you’re in trouble. In New York, baseline effort is assumed. This city is not easy. Service work here is athletic. Anyone acting like they’re grading a performance is setting themselves up to stiff someone with a straight face.

Another classic sign is the fake generosity flex. They announce they’re paying cash like it’s a gift to the restaurant. It’s not. Cash is neutral. Stinginess is not. Then they’ll calculate tax like it’s a loophole. If someone says “I don’t tip on tax,” you’ve already lost.

Pay attention when something goes wrong. Bad tippers love a mistake. A slow drink becomes a character flaw. A missing fork becomes a moral failure. They’re not interested in fixing the issue. They’re collecting excuses. In their mind, the tip is a reward they’re itching to withhold.

The most dangerous moment is the check split. Embarrassing tippers always want what they call “fair.” Fair somehow benefits them every time. They order more, drink more, complain more, then suggest an even split with a suspicious smile. This is not fairness. This is strategy.

Here’s the part nobody likes admitting. Bad tippers don’t think they’re bad people. They think they’re reasonable. They think everyone else is dramatic. They think New York is “too expensive anyway.” Meanwhile, the entire hospitality industry remembers exactly who they are.

If you’ve ever worked service, you already know this. You clock bad tippers the second they sit down. The posture. The tone. The way they snap for attention, then act inconvenienced when it arrives. None of this is accidental.

So what do you do? You fix it quietly. You overtip to rebalance the universe. You Venmo without announcing it. And next time, you choose your dining partners more carefully. Not everyone deserves a reservation.

Because in New York, tipping isn’t optional. It’s how you tell people who you are.

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