Episode 137 | Rotten Rhonda

Love is hard. Boundaries are harder. And your boyfriend’s about to cry again. This week, the Biffs dive into three emotionally chaotic conundrums: what to do when the dating drought has you questioning if marriage is even in the cards, how to end things with your boyfriend without emotionally wrecking him, and how to draw the line with your dad’s new wife without blowing up the family group chat. Stefani and Ray bring their signature, emotionally honest (and very unlicensed) advice to the romantically bewildered and boundary-confused. [Enrico Serafino Grifo del Quartaro Gavi di Gavi, 2021]

Show Notes

Sources:

• Dear Annie: How do I break up with my boyfriend without breaking him in the process? (https://www.cleveland.com/advice/2025/05/dear-annie-how-do-i-break-up-with-my-boyfriend-without-breaking-him-in-the-process.html#:~:text=Be%20honest%20with%20him%20in,him%20more%20in%20the%20end.)

• Dear Annie: Lack of relationships has me wondering if I’ll ever get married (https://www.cleveland.com/advice/2025/05/dear-annie-lack-of-relationships-has-me-wondering-if-ill-ever-get-married.html)

• Dear Annie: My dad’s new wife keeps overstepping boundaries (https://www.cleveland.com/advice/2025/05/dear-annie-my-dads-new-wife-keeps-overstepping-boundaries.html)