Poly Dating, Transparency & The Layers of Infidelity

In this episode of Tonight’s Conversation, live from Chicago, the panel dives into nontraditional relationships, starting with a couple seeking to add a male partner to their marriage—and the importance of being upfront about that dynamic from day one. The conversation expands to the complexities of cheating, from one-night mistakes to long-term affairs, exploring how the circumstances shape the healing process. The hosts debate whether someone who cheated can grieve the loss of their affair partner while trying to repair their primary relationship, and how triggers, trust, and transparency play into moving forward. They also challenge “over-healing culture,” set boundaries around double-dipping in grief, and highlight why not all relationships are worth trying to save.

00:00 Adding a Third Partner to a Marriage
03:00 Transparency in Poly Dating
07:00 Expectations, Agreements & Boundaries
10:00 Relationship Dynamics with Three Partners
13:00 When Infidelity Enters a Relationship
15:00 Punishment vs. Struggling to Forgive
17:00 Why Some Stay After Cheating
19:00 PTSD & Partner Betrayal
23:00 Saying “I Forgive You” Before You’re Ready
25:00 Can a Cheater Grieve Their Affair Partner?
29:00 Grieving the Version of Your Partner Before the Cheating
30:00 Levels to Cheating
33:00 Over-Healing Culture & Double-Dipping in Grief
35:00 Why Some Men Keep Cheating
37:00 Self-Awareness, Temptation & Discipline
38:00 Knowing Who You Are Before Committing
39:00 Setting Boundaries & Walking Away