Don't Ignore the Smoke: How to Spot Red Flags Before You Get Burned

Back when I was 24 and trying to get my first startup off the ground, I treated dating the same way I treated networking: sheer volume. I said yes to everything, ignored my gut, and assumed that if I just put in enough "work," things would click.

I remember a specific date with a woman I’ll call Vanessa. On paper, she was perfect. Smart, ambitious, great job in finance. But within the first ten minutes of sitting down at the bistro, my stomach tightened. Not butterflies—knots.

She wasn't explicitly mean. She didn't flip the table. But there was a coldness in how she corrected my pronunciation of the wine, and a weird intensity when she asked about my income. I ignored it. I told myself I was being judgmental. We dated for three months. It ended in a fiery wreck involving her keying my car because I had to work late on a Tuesday.

The red flags were there at 7:15 PM on the first date. I just chose not to see them.

Now that I’m 33, I don't have the time or the emotional bandwidth to "wait and see." In business, we have a saying: "Fail fast." In dating, it should be "Screen fast." Spotting red flags isn't about looking for perfection; it's about identifying fundamental incompatibilities and character flaws before you get emotionally invested.

Here is how to spot the smoke before the fire starts.

The "Service Staff" Barometer

You’ve heard this before, but I’m doubling down on it because it is the single most accurate predictor of character I have ever found.

Pay close attention to how your date treats the people who are paid to help them: the waiter, the bartender, the Uber driver, the coat check attendant.

I once went out with a girl who was charming, funny, and incredibly flirtatious with me. But when the waiter brought her sparkling water instead of still, she audibly sighed, rolled her eyes, and spoke to him like he was an incompetent child. "It’s really not that hard," she muttered as he walked away.

That mask she was wearing for me? That was temporary. The face she showed the waiter? That was permanent.

If they are rude, dismissive, or condescending to service staff, they are signaling that their kindness is conditional. It means they are nice only to people who have something they want (you). Once they "have" you, or once you stop being useful, that contempt will be turned on you.

The "Crazy Ex" Narrative

We all have baggage. If you’re over 30 and you claim you have no baggage, that is a red flag in itself. But there is a massive difference between having a past and living in it.

Listen carefully to how they talk about their previous relationships.

Red Flag A: The Victim Complex. If every single one of their exes was "crazy," "abusive," "psycho," or a "narcissist," run. While it is possible to have a run of bad luck, the common denominator in all those relationships is the person sitting across from you. People who refuse to take any accountability for past breakups will eventually paint you as the villain too.

Red Flag B: The Overshare. I went on a date last year where, within twenty minutes, I knew the details of her ex-boyfriend’s custody battle and his credit score. If they are talking about their ex on the first date with emotional intensity—whether it’s anger or longing—there is no room for you. The seat is taken.

Inconsistency: The Gap Between Words and Actions

As an entrepreneur, I live by data. People can tell you anything. Words are cheap. Action is the only metric that matters.

In the early stages of dating, people are usually on their best behavior. If their "best behavior" involves flaking on plans, showing up thirty minutes late without a text, or going silent for three days in the middle of a conversation, believe them.

I used to make excuses for people. "Oh, she’s just busy with work," or "He’s probably just bad at texting." Stop doing that.

If someone likes you, they prioritize you. It is that simple. I don't care if they are the CEO of a Fortune 500 company; if they want to see you, they will make the time.

Inconsistency is a major red flag because it signals a lack of respect for your time. If you tolerate flakiness early on, you are training them that your time is not valuable.

Love Bombing: Too Much, Too Soon

This one is tricky because it feels good.

Love bombing is when someone overwhelms you with affection, compliments, gifts, and promises of a future very early on. They might say things like, "I’ve never felt this connection before," or "You’re the person I’ve been waiting for," on the second date.

I fell for this hard in my late 20s. It feels like a movie. You think, Finally, someone who appreciates me!

But real intimacy is built slowly. It takes time to know someone. If they are putting you on a pedestal after two dates, they aren't falling for you; they are falling for a fantasy projection of you. And the moment you do something human—like have a bad day or disagree with them—you will be knocked off that pedestal just as fast as you were put up there.

Healthy interest looks like a steady simmer, not a grease fire. Be wary of anyone who tries to lock you down or define the relationship before they even know your middle name.

The Lack of Curiosity

This is a personal pet peeve of mine, but I think it reveals a deep character flaw: narcissism (or at least profound self-absorption).

A date is a tennis match. I hit the ball over the net; you hit it back.

I’ve sat through dinners where I asked question after question, dug into their life, their passions, their family, and their work. They happily answered everything, talking for forty-five minutes straight. And never once did they ask, "How about you?"

If you leave a date feeling drained because you had to carry the entire conversation, that is a red flag. A relationship with a person who lacks curiosity is going to be incredibly lonely. You will essentially be a supporting character in the movie of their life.

Trusting Your "Ick"

Finally, I want to talk about intuition.

Sometimes, there isn't a logical red flag. They are polite to the waiter. They ask questions. They text back on time.

But you feel... off. Maybe you feel anxious when you see their name on your phone. Maybe you feel the need to drink more than usual when you're around them to relax. Maybe you just feel a physical sense of repulsion (the "ick") that you can't explain.

Don't logic your way out of your gut feelings. Your subconscious mind picks up on thousands of micro-signals that your conscious brain misses—micro-expressions, tone of voice, body language discrepancies.

If something feels wrong, it usually is.

The Takeaway

Dating is not about convincing someone to like you. It is about finding someone who fits into your life and adds value to it.

When you spot a red flag early, don't view it as a disappointment. View it as a success. You just saved yourself three months (or three years) of misery. You freed up your time to find the person who won't snap at the waiter or talk about their ex all night.

Keep your standards high and your eyes open.