Tom Kelly has been a man in professional and mid life crisis since the pandemic hit five years ago—and he's been trying to make sense of the world ever since. In this heartfelt and funny episode, Tom shares a personal story about why he trusts psychic medium Winter Brook Ryan. Based in Northport, Long Island, Winter Brook explains what it really means to be a psychic medium and why she left behind a career as a lawyer to pursue her calling. Tom asks some personal questions about where to take his life in the next year and gets a message from his grandmother. The question is . . . which one?

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Comedian Olga Namer joins Tom Kelly for a wildly funny and disarmingly honest episode of The Tom Kelly Show. They dive into Long Island nightlife, Jewish family expectations, dating disasters, TikTok comedians, and the shame of wearing a Breathe Right strip in bed. The edibles are in full effect, but so is the heart. Comedy, chaos, and a crash course in boiling the perfect egg—this one has it all.

Chanel Omari – comedian, podcast host (Chanel in the City on iHeartRadio), and breakout star of Bravo’s Princesses of Long Island - shares she changed phone numbers and a 9 year old got her phone number. Now her old contacts, celebrities, Real Housewives from Bravo and maybe even Andy Cohen himself might be texting with a 9 year old (thinking it is Chanel). Tom shares his encounter texting with the 9 Year Old who has Chanel's old phone number.