Stavvy's World #153 - Caleb Hearon
Nov 3, 2025
Caleb Hearon, a stand-up comedian and podcaster known for his HBO Max special, dives into the quirks of dating and comedy. He shares hilarious dating mishaps, including an awkward 'four-hug' goodbye. Caleb recalls his coming out on Facebook and the wild reactions from friends and family. The duo also discusses their humorous take on wealth disparities and imagined buddy-comedy plots. With advice from listeners about non-monogamy and coping with loss, this conversation is packed with laughter and relatable insights!
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Early New York Hustle
- Caleb Hearon recounts hustling internships in New York after college to break into the city and comedy scene.
- He describes working as an RA/TA at Columbia, choosing light responsibilities to explore the city and attend open mics.
Feeling Like An Accidental Rich Guy
- Caleb and Stavros trade stories about feeling out of place in wealthy spaces after rising success.
- Stavros describes living in a luxe building and finding celebrity memorabilia in the trash as comic proof of unease.
Youth Is Prime For Sexual Experimentation
- Stavros and Caleb argue youth is the right time to experiment sexually and sexually permissive boundaries can be a gift.
- They stress different weight in choices made at 21 versus in your 30s when commitments solidify.