187. Sad Doesn’t Mean Broken - Real Talk on Mental Health & Dating w/ Dr. Caroline Leaf

187. Sad Doesn’t Mean Broken - Real Talk on Mental Health & Dating w/ Dr. Caroline Leaf

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 her new book Help in a Hurry, including how to create a 63-second pause to calm spiraling thoughts and respond with more clarity and confidence. We also talked about how past dating experiences shape our beliefs and how to gently rewire those patterns over time. This conversation was such a powerful reminder that we all have the inner wisdom to navigate hard moments, and that growth starts by giving ourselves compassion.


Mentioned in this episode:

Caroline's book: Help in a Hurry: Simple Tips for Finding Peace When You're Overwhelmed, Anxious, or Stressed

My episode on The Dr. Leaf Show - “Mastering The Art Of Dating”


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241. Dating With Different Cultural Backgrounds w/ Marina Iakovleva

241. Dating With Different Cultural Backgrounds w/ Marina Iakovleva

I'm chatting with Marina Iakovleva, creator of Dating Beyond Borders, who's spent 12 years exploring how people date around the world. We're discussing everything from why Scandinavians have sex befor...

27 Feb 53min

240. Stop Confusing Connection for Compatibility (Dating Dilemmas)

240. Stop Confusing Connection for Compatibility (Dating Dilemmas)

What happens when you have an amazing connection, but the relationship itself is kind of a bust? In this episode, I'm answering four dating dilemmas that all highlight the common dating mistake of con...

24 Feb 35min

239. Singles Events, Setups & Lessons From Vetting 800 Men w/ Alli Goldberg

239. Singles Events, Setups & Lessons From Vetting 800 Men w/ Alli Goldberg

Alli Goldberg (back for round 2!) is the creator and host of Love Isn't Blind, the live dating show where the men can't speak, and she's now hosted nearly 100 shows across 10 cities. That means she's ...

20 Feb 49min

238. When to Say "I Love You" (And Should You Say It First?)

238. When to Say "I Love You" (And Should You Say It First?)

I'm sharing my experiences with saying "I love you" for the first time, from awkwardly blurting it out in a noisy subway station to intentionally saying it over the phone. I'm covering the signs you'r...

17 Feb 26min

237. Surviving the Worst Parts of Dating w/ Rory Uphold

237. Surviving the Worst Parts of Dating w/ Rory Uphold

I'm chatting with Rory Uphold, a writer and the author of The Final Girl's Guide to the Horrors of Dating, a book that uses the horror movie framework to help people navigate modern dating. We're disc...

13 Feb 57min

236. When to Move In (And What No One Tells You About Living Together)

236. When to Move In (And What No One Tells You About Living Together)

You know you want to be with your partner for a long time, but how do you know when to move in? Today I'm sharing everything I've learned about moving in with a partner, from knowing when you're ready...

10 Feb 34min

235. Dating Red Flags That Predict Domestic Inequity w/ Laura Danger

235. Dating Red Flags That Predict Domestic Inequity w/ Laura Danger

Author and educator Laura Danger (@thatdarnchat) brought weaponized incompetence and the nag paradox into the mainstream, and today she's here to talk about how these dynamics can show up way before y...

6 Feb 53min

234. "His Best Friend Is A Woman. Is That A Red Flag?"

234. "His Best Friend Is A Woman. Is That A Red Flag?"

Feeling uneasy about your partner's friendship with someone of the opposite sex? You're not alone. In this episode, I'm breaking down what that jealousy actually means, when it's a you problem vs. a r...

3 Feb 24min

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