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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233. Why You Obsess Over Someone You Barely Know w/ Sabrina Bendory

233. Why You Obsess Over Someone You Barely Know w/ Sabrina Bendory

Sabrina Bendory, author of Detached: How to Let Go, Heal and Become Irresistible, joins me to break down what detached dating actually means (hint: it's not about not caring). We get into why you keep...

30 Jan 56min

232. Are You Staying for the Right Reasons? (Dating Dilemmas)

232. Are You Staying for the Right Reasons? (Dating Dilemmas)

I'm answering four real dating dilemmas from listeners stuck on whether to stay or leave a relationship. I get into how to end a medium-term relationship, what to do when you've been on the fence for ...

27 Jan 34min

231. What We Get Wrong About Avoidant Attachment w/ Travis Ambrose

231. What We Get Wrong About Avoidant Attachment w/ Travis Ambrose

I'm chatting with Travis Ambrose, an attachment-focused coach who specializes in helping people on the avoidant end of the spectrum heal and build healthier relationships. We're discussing everything ...

23 Jan 48min

230. Your First Date Pep Talk + Flirting Tips

230. Your First Date Pep Talk + Flirting Tips

Let's get ready for a first date! I'm sharing a pep talk for your next first date, plus my best quick tips for flirting, so you can actually create a romantic connection instead of just a friendly one...

20 Jan 28min

229. The 4 Things You Should Know by the 4th Date w/ Amy Nobile Messing

229. The 4 Things You Should Know by the 4th Date w/ Amy Nobile Messing

I'm chatting with Amy Nobile Messing, a holistic dating coach who "turbo dated" her way through NYC after leaving a 20-year marriage in her 40. She's now remarried and helping clients of all ages find...

16 Jan 52min

228. Signs They’re Ready for a Relationship

228. Signs They’re Ready for a Relationship

I’m breaking down the real signs someone is actually ready for a relationship beyond what they say on a dating app or how excited they seem early on. I’m also covering what doesn’t mean much on its ow...

13 Jan 27min

227. Dating When You've Never Been In A Relationship w/ Allora Dannon

227. Dating When You've Never Been In A Relationship w/ Allora Dannon

In this episode, I'm chatting with Allora Dannon, who went on her first date ever at 32. She's now engaged, and we're discussing everything from how to bring up your lack of experience on a date to na...

9 Jan 54min

226. 8 "Red Flags" That Are Normal in Long-Term Relationships

226. 8 "Red Flags" That Are Normal in Long-Term Relationships

In this episode, I'm breaking down 8 things that seem like red flags but are actually just part of being with someone for a while, like feeling bored sometimes, not being "in love" every single day, h...

6 Jan 35min

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