Welcome to The Tom Kelly Show — where midlife reinvention meets Long Island sarcasm. Tom is joined by his hilarious high school friend from Long Island Lutheran High School, fashion executive Daniela Anastasio, and things get real (and ridiculous) fast. They’re talking: 👉 Ozempic: Is it making people hot, boring... or unfaithful? 👉 Long Island hot takes: North Shore vs. South Shore girls 👉 And yes... Tom might be afraid of South Shore women

Verizon’s customer service is so bad, Tom Kelly suspects it’s secretly run by Mint Mobile. Joined by the brilliantly dry Steve Burger at Roosevelt Field — the last thriving mall on Long Island — Tom unloads about tech drama, AI sabotage, exploding boba, and content creation chaos. Yes, we talk Teslas. Yes, Tom has GPS trust issues. Yes, we buy mangoes in traffic.

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?

Winter's Website:

Winter's Instagram:

Winter's Facebook:

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.

Comedian Olga Namer pops into the New York studio—and pops an edible—for a hilarious, honest, and surprisingly deep conversation. From growing up Orthodox Jewish in Brooklyn to smoking weed (kind of) with Owen Wilson, Olga dishes on life, love, ChatGPT therapy, and being just high enough to spill it all. Tom and Olga explore:

Anxiety and edibles

Why comedians outsource their self-worth

What it means to grow up modern Orthodox

The chaos of dating as a Jewish woman in NYC

The power (and limits) of ChatGPT as your therapist

A week ago, Tom Kelly made a joke about asking President Donald Trump to Save the Massapequa Chief. A week ago, Tom Kelly made a joke about asking President Donald Trump to Save the Massapequa Chief. Tom promised to deliver 100 All American Hamburgers if President Trump saved the Massapequa Chief. Now reality is mimicking comedy . . .

This week, President Trump is in the White House with Fox News’s Brian Kilmeade making it happen. President Donald Trump has asked Secretary of Education Linda McMahon to save Massapequa mascot . . . the Massapequa Chief. The U.S. Department of Education announced Friday it plans to investigate whether New York education officials are being discriminatory by threatening to withhold funding if a Long Island school district doesn't stop using a Native American-themed logo.