Ep21: Her Cup Runneth Over—with Tips and Creepy Vibes

Gwen and Tim are back with hot takes and hotter coffee shop drama. First, they unpack a barista’s $800 tip jar full of romantic delusion and boundary issues—was it generosity or manipulation in disguise? Then it’s onto scratched pans, emotional growth, and a marriage under stress when one partner turns down the “dream job.” Finally, a FIRE couple questions whether they’re saving too much and living too little—plus, what not to do with a million-dollar inheritance that hasn’t landed yet. Come for the takes, stay for the simmering tension.