Bachelor and bachelorette parties are often sold as the “last night of freedom,” but do they truly honor marriage—or undermine it? Jeff and KAT unpack the ancient history of stag nights, the feminist roots of bachelorette parties, and the modern-day commercial machine behind them. From Hollywood glamorization to the reality of peer pressure, strippers, and regret, they ask the real question: Should this tradition continue, or is it time to let it go.

Engagement is a bridge, not a destination. But how long should that bridge be? Jeff and KAT weigh the pros and cons of short versus long engagements. They cover everything from momentum, planning, and family integration to the risks of stalling and losing spark. Drawing on personal stories—including their own whirlwind engagement—they highlight how alignment, strategy, and honesty are key to making engagement meaningful.

How do you know when your dating journey has reached its natural peak? In this episode, Jeff and KAT dive into the six signs that your relationship may have plateaued. From conversation loops and recurring conflicts to future fog and obligation traps, they explore how to tell whether your relationship is moving forward—or just spinning in circles. Learn how to recognize when it’s time to deepen your commitment, or when it might be healthier to walk away.