The Biggest Fears in Dating (and How to Overcome Them) | Rewind

The Biggest Fears in Dating (and How to Overcome Them) | Rewind

Why do we get so in our heads when we start dating someone new? In this episode, we dive deep into the most common fears people face in early dating — from getting too invested too soon, to navigating intimacy and exclusivity when someone’s seeing multiple people.


With over 1,300 comments from listeners sharing their biggest dating anxieties, we unpack the most relatable ones and offer real, practical ways to reframe them. You’ll hear us talk about:


  • What it really means when someone wants intimacy but avoids emotional connection
  • How to slow down without feeling like you’re “falling behind”
  • Why obsession isn’t chemistry — and how to trust yourself more in the process
  • The mindset shift that turns “what if I get hurt?” into “what if I stay grounded?”


If you’ve ever found yourself overthinking a text, reading too much into mixed signals, or getting attached too fast — this one’s for you.


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►► Looking for love, clarity, or a fresh perspective? Matthew’s weekly newsletter dives into insights that transform not just your relationships, but your entire life. Sign up for free at TheThreeRelationships.com

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Do Men EVER Change?! (I Did...) | Matt Monday

Do Men EVER Change?! (I Did...) | Matt Monday

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Why You Become “Too Nice” When You Like Someone | Rewind

Why You Become “Too Nice” When You Like Someone | Rewind

Have you ever noticed the moment it happens?You meet someone, you’re fine… and then suddenly you really like them and you start editing yourself. You become agreeable. Overly available. “Easy.” And it...

20 Feb 28min

Why Men Don’t Open Up These Days... | Matt Monday

Why Men Don’t Open Up These Days... | Matt Monday

I hear this all the time: “Matthew, they’re wonderful but they won’t let me in. The conversations stay shallow. They deflect when things get real. And no matter how safe I try to make it, they just . ...

16 Feb 12min

How to Overcome Feeling “Not Good Enough” in Love | Rewind

How to Overcome Feeling “Not Good Enough” in Love | Rewind

We often talk about how the right partner will elevate your best and soothe your worst. But what if you secretly feel like your best isn’t good enough . . . or that your worst will be “too much“ for s...

13 Feb 14min

What Dating Burnout Is Actually Doing to Your Brain — w/ Dr. Guy Winch, Part 2

What Dating Burnout Is Actually Doing to Your Brain — w/ Dr. Guy Winch, Part 2

Dating can burn you out . . . especially when you’ve been rejected, ghosted, or stuck in that exhausting loop where nothing ever turns into something real. In Part 2 of my conversation with clinical p...

11 Feb 53min

The Most Powerful Message to Your Ghoster | Matt Monday

The Most Powerful Message to Your Ghoster | Matt Monday

When you’re ghosted, the silence feels intensely personal. In this new episode, I'm breaking down what’s really going on when someone ghosts: why it happens at different stages, and how to respond wit...

9 Feb 13min

3 Simple Ways to Make a Lasting Impression on a First Date | Rewind

3 Simple Ways to Make a Lasting Impression on a First Date | Rewind

Everyone wants to stand out on a first date… especially when it feels like the person across from you has endless options. But the real way to become unforgettable isn’t performing, impressing, or say...

6 Feb 12min

Why You’re Always Exhausted (Even When You’re Not Working) – w/ Dr. Guy Winch, Part 1

Why You’re Always Exhausted (Even When You’re Not Working) – w/ Dr. Guy Winch, Part 1

Work has a way of following us home—replaying that one frustrating meeting, stealing our attention from the people we love, and turning Sunday night into a countdown to stress. In this conversation wi...

4 Feb 1h 2min

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