🚩 First Dates Are Fun... But Third Dates Spill the Tea

Let's skip dating red flags together!

Let’s face it: first dates are all smiles, charm, and maybe a shared dessert. But by date #3? That’s when people start getting comfortable—and sometimes a little too comfortable. After 30+ years as a dating coach (yes, really—and I still love it!), I’ve seen it all unfold right around the second or third encounter.

Here are 10 subtle red flags to keep your eye on before you fall for the wrong one:

1. Right Person, Wrong Timing

Ugh, the classic! They could be perfect… six months from now. He just finalized a divorce. She’s caring for a parent, juggling a new job, or recently moved. Timing isn’t just a cliché—it’s everything. “The One” should also be “The One right now.”

2. The Vanishing Act

Great first date. You make second-date plans. Then… poof! Ghosted or hit with flimsy excuses. If they can’t follow through this early on, trust me—it doesn’t get better.

3. It’s All About Me, Me, Me

You’re nodding politely as he details his golf swing... for 45 minutes. No questions for you? Try this: “Wow, I feel like I know your life story. What would you like to know about me?” If they still don’t ask? 🚪➡️

CLICK HERE!

4. The Chronic Venter

She’s ranting about online dating, her ex, her kid’s tuition, the weather... If that’s what Date #2 sounds like, imagine Date #20. Negativity isn’t sexy. No matter how cute they are—skip it.

5. Distracted Dater

Checking their phone. Looking at their watch. Staring at the wall. You deserve someone who’s present, not someone mentally browsing Zillow mid-convo.

6. Evasive Maneuvers

If they dodge basic questions (job, hobbies, where they live), something’s off. You’re not interrogating—just trying to have a normal conversation. Red flag if you feel like you're dating a spy.

7. The Over-Texter

My client Lara liked Chris… until he started texting constantly. Like, every few hours. When she asked for space? He said, “I miss you.” 🚨Stage 5 clinger alert. She moved on to a guy with healthier thumbs.

8. Hot and Cold

One day they’re into you, the next? Crickets. You deserve consistency, not emotional whiplash.

9. Can’t Make a Plan to Save Their Life

If it’s all talk, no action—buh-bye. Also: “I dunno, whatever you want to do” is not a plan. Great daters show up and plan. (Shoutout to Hunter, my client who biked 14 NYC bridges on a first date—epic!)

10. Talks $$$ Too Much

Whether it’s humble-bragging about Teslas and Tuscany or whining about exes and child support, it’s a no. Financial over-#sharing early on screams insecurity, not stability.

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Ready to Decode the Signals—and Attract the Right One?

That’s where I come in. I help singles over 40, 50, and beyond actually enjoy dating again (crazy concept, right?).

Summer’s peak dating season. Don’t sit this one out—let’s talk and see how I can help you thrive online.

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Because if not now… when?