Episode 108: How To Know When It’s Time to Go (Part One)

How do you know when a relationship is going through a hard season—and when it’s actually time to go?

In this episode of herspective, Jillian and Andrea dive into one of the hardest questions to answer when you’re deeply invested in someone: Should I stay, or should I leave?

They unpack why walking away can feel so complicated, especially when your lives are intertwined, you’ve invested years into the relationship, or leaving means letting go of the future you thought you were building. From marriage and children to shared homes, finances, expectations, and the pressure of watching everyone else seemingly move forward, sometimes what keeps us in a relationship isn’t simply love—it’s everything we’re afraid we’ll lose by leaving.

Jillian opens up about the months leading up to the end of her engagement, including the repeated boundary violations, unhealthy conflict, and moments that slowly shifted her question from “Can we fix this?” to “Is staying here costing me more than leaving?” She shares how therapy, prayer, and finally recognizing the patterns in front of her helped her find the clarity to walk away.

Andrea reflects on her own marriage and divorce from a different perspective: what happens when conflict is avoided altogether. She shares how issues left unspoken can quietly accumulate until the relationship experiences what she describes as “death by a thousand cuts”—and how that experience shaped the way she approaches communication and relationship check-ins today.

Together, they explore boundaries, toxic patterns, healthy conflict, trauma bonds, communication, trusting what your body may be telling you, and the courage it takes to follow through once you know something needs to change.

This isn’t an episode about leaving when relationships get hard. It’s about recognizing when the work is mutual, when conflict can create connection, and when repeatedly sacrificing your boundaries, peace, or sense of self is no longer something you should have to call love.

And this conversation isn’t over yet. Jillian and Andrea continue exploring how to know when it’s time to go in the next episode.