In the special Valentine’s Day episode of The Shady Chronicles podcast, co-hosts Des and Kiara dive deep into the highs and lows of love and relationships. They kick things off by sharing their own hilarious or cringe-worthy Valentine’s Day mishaps, recounting some of their most memorable (and regrettable) experiences. Then, the duo gets playful with a game of “Shady Cupid,” where they let their imaginations run wild, imagining their favorite celebrities coupling up or breaking up in the most dramatic (and shady) ways possible.

As they continue, they tackle some of the common “Valentine’s Day violations” — from misguided gifts to awkward dates — and discuss how people’s self-worth is often tied to romantic gestures. Des and Kiara keep it real about the pressure to feel loved on a day that’s all about love, reminding listeners that true worth isn’t determined by flowers or chocolates. It’s a perfect blend of fun, humor, and heartfelt moments that will leave you laughing and thinking about love in a whole new way.