Crying in Chili's · Aug 14, 2026 · 1:13:49
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When Baggage Becomes Wisdom
Sarah is back for round three, and this time we're talking about dating, being intentionally single, learning to actually enjoy your own company, and the relationship lessons we had to learn the hard way.
Courtney gives the full story behind the sweaty mini-golf date that unexpectedly went viral, including 93-degree weather, a bathroom with no paper towels, an emergency hand-dryer situation, and hundreds of thousands of strangers suddenly having opinions about it.
Then things get a little deeper. Sarah shares why she's choosing not to date right now, we unpack the difference between being alone and feeling lonely, and we talk about losing yourself in relationships, anxious attachment, setting boundaries, and recognizing when past experiences are still baggage — or when they've finally become wisdom.
Also discussed: dating people who are still legally married, peeing in kitchen sinks, why your friends should occasionally give you a come-to-Jesus talk, and the revolutionary realization that a relationship doesn't have to be the end goal.
Sometimes the relationship you need to work on most is the one you have with yourself.