In this episode, Dr. Caroline Leaf and I are bringing you the conversation about what it really means to “not be okay”, especially when it comes to dating and our mental health. We cover why sadness or anxiety doesn’t mean we’re broken, and how the pressure to be constantly happy or healed can actually make things worse. Caroline shared practical tools from ... Show More
Oct 7
201. Why It’s So Hard to Walk Away (And How to Finally Do It)
In this episode, you'll learn how to know when to walk away in early dating vs. long-term relationships and why it's so difficult. You’ll get a simple mindset shift that makes the breakup decision stick, plus exact scripts to end it by text, phone, or in person without reopening ... Show More
40m 1s
May 2025
(Matt Monday): How to Make Them CHASE YOU Without Playing Games
The rules of modern dating can feel so confusing. You don’t know how much texting is too much, how to make the first move, or whether to keep trying if their interest is hot and cold. In this week’s video, I sat down with bestselling author Jay Shetty for his On Purpose podcast t ... Show More
20m 4s
Mar 2025
(Rewind): How to Make Them CHASE YOU Without “Playing It Cool”
We’ve all been told that we should never come on too strong, and that playing it cool is the best way to get someone interested. But how much interest is the right amount to show in the early days of dating? If we show too much interest, we worry we’ll lose all our “power,” but i ... Show More
18m 40s
Sep 3
Jared Freid & Jordana Abraham: Dating App Burnout? Do THIS 30-Day Challenge to Stop Wasting Time and FINALLY Meet the Right Person
Are you making time for the kind of love you want? Do you feel like you’re ready to stop repeating old patterns? Today, Jay welcomes Jared Freid and Jordana Abraham, hosts of the hit dating podcast U Up?, for a candid, lighthearted look at modern love. Together with Jay, they unp ... Show More
1h 15m