The Waiter Test & Other Early Warning Signs: A Guide to Spotting Red Flags

I remember sitting across from a woman I’ll call Jessica at a tapas bar in downtown Austin. On paper, she was perfect. She ran her own marketing agency, loved hiking, and had a dry sense of humor that matched mine. We were twenty minutes into the first date, and I was mentally planning our third.

Then, the waiter made a mistake. He brought sparkling water instead of still.

Jessica didn’t just correct him. She sighed, rolled her eyes, and spoke to him with a condescending tone that sucked the air right out of the room. "Is it really that hard to distinguish between bubbles and no bubbles?" she asked, not looking at him, but looking at me for validation.

That was the moment the date ended for me. Physically, I stayed for another hour. But mentally? I had already closed the deal and walked away.

In my early twenties, I would have ignored that. I would have told myself, "She's just having a bad day," or "She's particular, that's good, she has standards." I would have focused on the chemistry and the shared interests. And I would have wasted six months dating someone who lacked basic empathy, only to have it blow up in my face later.

As an entrepreneur, I spend a lot of time vetting business partners. If a potential partner is shady about their finances or rude to my staff, I don't sign the contract. Dating requires the exact same level of due diligence. We call them "red flags," but really, they are data points. And if you ignore the data, you’re going to go bankrupt emotionally.

Here is how to spot those red flags early, before you’re too invested to walk away.

The "Service Staff" Litmus Test

Let’s start with the Jessica situation because it is the single most reliable indicator of character I have ever found.

How your date treats people they aren't trying to impress—waiters, bartenders, Uber drivers, the janitor—is how they will eventually treat you once the "new relationship smell" wears off.

When someone is courting you, they are in sales mode. They are showing you their best features. But they don't feel the need to "sell" themselves to the server. That interaction is their baseline. If they are dismissive, rude, or entitled with service staff, that is a massive red flag. It shows a lack of empathy and a hierarchy-based view of human value.

Actionable Tip: Watch what happens when something goes wrong. If the food is cold or the drink is wrong, do they handle it with grace and polite correction? Or do they get indignant? Grace under minor pressure is a green flag. Indignation is a warning shot.

The "Crazy Ex" Narrative

We all have baggage. If you’re in your thirties and you say you have no baggage, you’re either lying or you’ve been living in a bunker. But pay close attention to how your date discusses their past relationships.

If they mention an ex, that's normal. But if every single one of their exes was "crazy," "toxic," or "psycho," you have found the common denominator.

I once went out with a girl who spent 45 minutes of our first date detailing how her last three boyfriends had victimized her. According to her, she was a perfect angel, and they were all monsters. There was zero self-reflection.

People who cannot take ownership of their role in failed relationships will not take ownership when things go wrong with you. They view themselves as perpetual victims, which means you will eventually become the next "crazy ex" in their narrative.

The Fix: Listen for nuance. A healthy perspective sounds like, "We wanted different things," or "We struggled to communicate, and it didn't work out." That shows maturity. "He was a total psycho who ruined my life" shows volatility.

Love Bombing vs. Genuine Interest

This is a tricky one because it feels so good.

"Love bombing" is when someone showers you with excessive affection, compliments, and future-faking very early on to gain control or accelerate intimacy.

If you are on date two and they are telling you that you are their soulmate, that they’ve never felt this way before, or they are planning vacations six months out, your alarm bells should be ringing.

In business, if a deal looks too good to be true, it usually is. If an investor wants to give me a million dollars without seeing my P&L sheets, I’m suspicious. In dating, intimacy must be earned. It takes time to get to know someone. If they claim to love you before they know your middle name or your traumas, they don't love you. They love the idea of you, or they are desperate to fill a void.

Real connection burns slow. Infatuation burns hot and fast—and usually burns out just as quickly.

The Boundary Stomp

A few years ago, I went out with a woman who wanted to go to a specific club after dinner. I told her, "I’ve got an early meeting tomorrow, so I’m going to call it a night after this drink."

She pouted. Then she cajoled. Then she got aggressive. "You’re being boring. Just one drink. Don't be lame."

It seems small, right? Just peer pressure? No. That was a boundary violation.

I set a clear limit regarding my time and my needs. She decided that her desire to party was more important than my stated boundary.

Pay attention to the small "no." If you say you don’t like a certain food, and they try to force you to try it. If you say you’re not ready to sleep together, and they keep pushing or make you feel guilty. If you say you need a night to yourself, and they text you incessantly.

These are not "cute" persistence tactics. They are signs that this person does not respect your autonomy. If they stomp on small boundaries now, they will bulldoze big boundaries later.

Inconsistency in Communication

I’m a busy guy. I run a business. I understand not texting back immediately. But there is a difference between being busy and being inconsistent.

The "hot and cold" dynamic is a major red flag. This is the person who texts you non-stop for three days, creating a false sense of intimacy, and then vanishes for four days with no explanation. Then, they pop back up with a "Hey stranger!" text as if nothing happened.

This behavior usually indicates one of two things:

1. They are emotionally unavailable and get spooked when things get real.
2. They are keeping you on the back burner while they pursue other options.

Consistency is the currency of trust. You cannot build a relationship with someone whose attention is volatile. You end up anxious, constantly checking your phone, wondering what you did wrong. The answer is usually: nothing. You’re just dating someone who is playing games.

Trusting Your "Gut" Data

Finally, the biggest red flag is often an internal one: Your own intuition.

Our subconscious is a powerful pattern-recognition machine. It picks up on micro-expressions, tone of voice, and body language that our conscious mind might miss.

If you leave a date feeling drained, anxious, or just "off," listen to that. Don't talk yourself out of it. Don't rationalize it by saying, "Well, they check all the boxes on my list."

I once dated a woman who was perfectly polite, successful, and beautiful. But every time I left her apartment, I felt exhausted. I couldn't put my finger on it. Later, I realized she was incredibly passive-aggressive, making tiny digging comments that flew under my radar but landed in my subconscious.

If you feel like you have to walk on eggshells, or if you feel the need to "perform" rather than just be, that’s a red flag.

The Takeaway

Dating is supposed to be fun, but it’s also a vetting process. You are the CEO of your own life. Who you choose to bring into your inner circle is the most important hiring decision you will ever make.

Don’t fear the red flags. Be grateful for them. They are the road signs telling you to turn around before you drive off a cliff. When you spot them, don't try to paint them white. Don't try to fix the person.

Believe people when they show you who they are the first time. It will save you months of heartache and leave you open for the person who actually deserves your time.