Why Do My Dates Feel Like Interviews?

The good men in my community have shared many stories of dates that feel like interviews where the women seem guarded and cold.

I get it. It's frustrating, especially when you're a genuinely great guy just trying to get to know someone.

But here's what's actually happening underneath that.

Many women in their 50s and 60s have spent years over-functioning... caretaking, problem-solving, holding it together for everyone else. That doesn't just switch off the moment a date starts. It takes practice for women to feel safe enough to soften and let someone in.

So instead of reading her guardedness as rejection, try reading it as the starting point and an opportunity to take the lead.

Your job isn't to win an interview with her. It's to help her feel safe enough to actually open up and let you in.

Here are 2 ways you can do that.

1. Tell her something real about yourself. A life story. Something you've learned about yourself on your own dating journey. That vulnerability gives her a reason to lower her guard too.

2. Ask her deeper questions. Something like... what's something in your life you're most proud of? Who's been the most impactful person in your life, and what's the most important thing they taught you? Then really listen. Reflect some of it back to her, so she feels seen.

The right woman will follow your lead... and that's when the interview ends, and the real connection begins.

❤️ Megan

I’m a Dating Concierge for singles in their 50s and 60s who are trying to navigate this modern dating world.  Through my company Throwback Dating I create fun opportunities for singles over 50 to connect organically.  No more games, no more dating pressure.