You can listen to a short excerpt of our conversation here, or head to Spotify, Apple Podcasts, or YouTube to catch the entire episode
I sat down with Michael Amory, a New York–based therapist, and this conversation hit on something I see every single day with my clients: people are overthinking dating to the point that they’re not actually dating.
They’re stuck. Frozen. Waiting to feel 100% certain before making a move.
And that’s exactly why they’re still single.
Michael brought a really refreshing perspective—one that blends clinical insight with real-life practicality (and honestly, a sense of humor that most therapists don’t lean into enough).
Here’s what stood out to me—and what I want you to take with you into your next date.
1. You Need to Stop Taking Dating So Seriously
This might sound counterintuitive coming from a matchmaker, but it’s the truth.
If every date feels like it has to lead to marriage, you’re going to burn out quickly—and you’re going to come across as intense.
Michael made a great point about humor being a tool—not just in therapy, but in dating. Laughter helps you and your date relax. Don’t take yourself so seriously!
The people who do best in dating aren’t the ones who are the most perfect—they’re the ones who are the most at ease.
2. Indecision Is Keeping You Single
I see this constantly.
You have options. You’re dating multiple people. And instead of leaning in and exploring one connection, you stay in this gray area… analyzing everything.
“What if there’s someone better?”
“What if I make the wrong choice?”
Here’s the reality: you will never feel 100% sure.
Dating requires decision-making. And most people are avoiding it.
Michael compared dating to poker—you have to be willing to place a bet without knowing exactly how it will turn out.
And if it doesn’t work? You move on. But sitting in indecision is what keeps you stuck.
3. You Have to Be Willing to Take Risks
This is where people lose opportunities.
They want the perfect setup, perfect timing, perfect feeling.
It doesn’t exist.
You’re going to have to:
Go on dates you’re unsure about
Say yes when it feels slightly uncomfortable
Invest in someone before you have all the answers
That’s how you build something real.
Every relationship—whether it lasts or not—teaches you something. And those lessons are what ultimately lead you to the right person.
4. Everyone Thinks the Other Side Is the Problem
This part of the conversation made me laugh because it’s so accurate.
Women tell me: “Men aren’t serious.”
Men tell me: “Women are too picky.”
Both sides feel frustrated. Both sides feel misunderstood. And most of it comes down to poor communication and unrealistic expectations.
Instead of focusing on what’s wrong with the other side, start asking:
Am I clear about what I want?
Am I communicating that directly?
Am I actually open to the kind of person I say I want?
The goal isn’t perfection—it’s compatibility.
And that requires honesty on both sides.
5. You Can Always Choose Again
This is the mindset shift that changes everything. People treat dating decisions like they’re permanent, which they’re not.
You go on a date → you see how it feels → you decide what to do next.
That’s it.
You’re not choosing your life partner on date one. You’re choosing whether you want to see them again. When you simplify it like that, dating becomes a lot less overwhelming—and a lot more effective.
The Bottom Line
Dating isn’t about getting it perfect.
It’s about:
Showing up
Making decisions
Taking risks
Learning as you go
And most importantly—staying open.
If you’re waiting to feel completely certain before you move forward, you’re going to be waiting for a very long time.
