Welcome to the Heartbreak Hotel! Check into a different hotel every Wednesday with Caitlin Erin O’Neill and a new guest as they share their stories navigating today’s dating climate and lock in as they divulge everything from their best to their messiest and most toxic relationship experiences. Get relationship, situationship, and imaginationship advice on Heartbreak Hotline by submitting your questions to our socials and play Red Flag Green Flag as Caitlin & Heartbreak Hotel guests give their honest opinions on every quirk that you don’t know what to make of yet. We hope you enjoy your stay!