10 Red Flags to Watch for on the First Three Dates (And What to Do Instead)

The experiences shared in this article are based on real emotional journeys, but all personal details are anonymized and used with the explicit written permission of the clients. Any resemblance to actual persons, living or dead, is purely coincidental. We are committed to treating all client stories with the utmost confidentiality and respect.

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1. He Monopolizes the Conversation

A first date isn’t a TED Talk audition.

If he spends 80% of the time talking about his crypto portfolio, his “haters,” or his ex’s “trust issues,” take note.

The Core Problem: Healthy connection requires reciprocity.

A client, Sarah, once endured a two-hour monologue about a guy’s fantasy football league.

When she finally interjected, he said, “Sorry, I just love hearing myself talk.”

They did not have a second date.

Shift the Dynamic: Gently redirect: “That’s interesting! What’s your take on [topic you care about]?” If he steamrolls again, thank him for the coffee… and ghost respectfully.

2. He Negs or “Jokingly” Insults You

Backhanded compliments like “You’re pretty smart for a blonde” or “I usually date models, but you’re cute” aren’t flirty—they’re manipulative.

Behind the Behavior: Negging is designed to undermine your confidence, keeping you eager to “prove yourself.”

A client, Mia, received “You’d be hotter if you smiled more” on date one.

By date three, he’d criticized her job and friends.

Stand Your Ground: Call it out calmly: “That comment felt off. What did you mean by that?” His reaction tells you everything.

3. He Pressures You to Skip Boundaries

Whether it’s pushing for another drink, insisting you come back to his place, or demanding nudes, boundary-pushers reveal themselves fast.

The Bigger Picture: Respect isn’t negotiable.

I once left a date mid-appetizer because a guy wouldn’t stop “playfully” tugging my sleeve after I said “Don’t.”

Your Power Move: Use the “Broken Record” technique: Repeat your boundary firmly (“I said no”) without justifying. If he persists, leave.

4. He’s Vague About His Life

Mystery is sexy; secrecy is suspect. If he dodges basic questions (“What do you do weekends?” → “Stuff”) or gives conflicting details, tread carefully.

What’s Lurking: Inconsistencies often hide dealbreakers. A client, Jess, dated a guy for a month before learning he had two kids… and a wife.

“He’d always change the subject when I asked about his ring tan line,” she said.

Dig Deeper: Ask open-ended questions (“How’d you get into your career?”). If answers feel rehearsed or evasive, Google him. Yes, really.

5. He Talks Smack About Everyone

If he rags on his “crazy” ex, his “jealous” friends, and his “idiot” boss, guess who’s next? Spoiler: You.

Pattern Recognition: Chronic negativity signals emotional immaturity.

My client, Lauren, ignored this red flag until her date snapped at a waiter for forgetting ranch. “Suddenly, I was walking on eggshells,” she said.

Test the Waters: Notice if he shows empathy for others. Ask, “What’s something you admire about your best friend?” If he can’t answer, 🚩.

6. He Love-Bombs

Sweeping declarations (“I’ve never felt this way before!”), excessive gifts, or future-faking (“Let’s book a Bali trip!”) on date one? Pump the brakes.

The Trap of Intensity: True intimacy grows slowly.

A guy once showed up to our first date with roses, a handwritten poem, and tickets to Paris. Charming? Sure. Healthy? Nope. He ghosted two weeks later.

Slow the Roll: Say, “I’m enjoying getting to know you slowly.” If he backpedals or gets defensive, he’s likely scripting a fantasy, not building a relationship.

7. He Can’t Handle Mild Conflict

Watch how he reacts to tiny hiccups—a wrong order, a rainy day, or you disliking his favorite band. Defensiveness or sulking = trouble.

Stress Test: Life has bigger stressors than cold fries. A client’s date yelled at a valet for scratching his car… then blamed her for “killing the mood.”

Read the Room: Test the waters: “I actually disagree—I think Inception is overrated.” If he mocks or dismisses you, he’s not partnership material.

8. He’s Glued to His Phone

Occasional texts? Fine. Scrolling Instagram while you’re mid-sentence? Rude.

Priority Check: It shows where his focus lies.

A guy spent our entire second date texting his fantasy league group chat.

When I asked, “Should we reschedule?” he said, “Nah, I can multitask.”

Spoiler: He couldn’t.

9. He “Jokes” About Your Dealbreakers

If you mention wanting kids someday and he says, “I’ll just ‘forget’ to pull out”… run.

Testing Your Limits: “Jokes” often mask boundary probes.

A client’s date laughed about “taming her feminist rants” after she mentioned her women’s rights volunteer work.

Flip the Script: Stay silent and stone-faced. If he backtracks (“It was just a joke!”), say, “Explain why it’s funny.” Watch him squirm.

10. Your Friends Hate Him

If your squad says, “He gives me the ick” or “Something feels off,” listen.

The Outsider’s Lens: Loved ones spot red flags we rationalize away.

I once ignored my bestie’s “He’s performative” warning about a guy who brought his therapy journal to dates.

Turns out, he was rehearsing lines.

Trust Your Tribe: Ask a trusted friend: “What’s your gut say about him?” If they hesitate, dig deeper.

Final Words from The Darling Code

Red flags aren’t flaws to fix—they’re data to honor.

You’re not “too picky” for wanting respect, consistency, and basic human decency.

The right person won’t make you decode mixed signals. They’ll show up—fully, clearly, kindly—and leave no room for doubt.

With heart,
The Darling Code

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