Hard Things to Bring Up in Therapy: What We’re Afraid to Ask

In this episode of Hard Things to Bring Up in Therapy, we sit down with the questions people are often too afraid to ask out loud — the ones about love, loss, sex, shame, attachment, boredom, longing, and the quiet fear that maybe something is wrong with us.

From wondering why “healthy love” feels boring after toxicity… to grieving a breakup someone else moved on from too quickly… to asking how often long-term couples should be intimate… to questioning why we attract emotionally unavailable partners… to the messy, human moments around sex, desire, loneliness, and readiness.

These are the things we carry alone. This episode sets them down in the open.

Why This Episode Matters

These aren't just questions — they’re emotional crossroads.Most people bring them into therapy last, if ever.But naming them is the beginning of healing, clarity, and choosing differently.

Perfect For You If…

You’re in a season of confusion about love or relationships

You’re healing from a breakup

You’re dating but frustrated by your patterns

You want a healthier relationship with intimacy and connection

You’re afraid to ask the questions that matter most

Listen Now

Every question in this episode is a doorway. Step through.

📘 Read John’s new book in progress Sh*t Your Therapist Would Never Tell You on John’s SubStack ⁠HERE⁠

If you’re ready for deeper work, the Secure Self course is available HERE

Order John's new book, Break Up. On Purpose,⁠⁠ ⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠⁠

Follow John on Instagram⁠⁠⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠⁠

Find out more about John⁠⁠⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices