Ready to get weird and wise? Jordan and J.T. play the first round of Uncomfortable On Purpose. Think Truth or Truth: the questions you’d rather not ask your partner but really should.

This round cuts deep. A provocative and revealing Q&A-style game that digs beneath the surface. Topics we usually tiptoe around—shame, addiction, fear, failure—but with the goal of healing, not harm. A darkly playful excavation of your emotional scar tissue—because healing can be sexier with a bit of risk.

The FIVE subversive and intentionally uncomfortable categories are tailored to spark meaningful conversation, shared vulnerability, and unexpected insight.

CATEGORIES: Spicy Confessions, Past Lives, Mirror Work, Trigger Warning, and Romance Round 2!

Real talk about second chances at love, adult intimacy, and all the weird, wonderful shit that comes with being human.

Don't just eavesdrop - try it! If you'd like a starter kit of playful heat, send a request to letsdigintothat@gmail.com

Let the awkwardness be part of the vibe.

If you have an inquiry or topic you’d like Jordan and J.T. to dig into, please send an email or voice memo to letsdigintothat@gmail.com

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