After four long years, the moment no one has been waiting for has arrived: I’m Sure I’m Overthinking This Season 2 begins this week. I’m not the type to use exclamation points, but I really think that previous sentence deserves one. Either way, Season 2 starts this Thursday with FS1 and SiriusXM’s Nick Wright.

This week’s guest is Tyler Gildin, stand-up comedian and executive producer at Elite Daily. Here’s some of the stuff we talked about: when did he first realize he was funny? (2:10), what he was like, comedically, growing up and through school (3:05), why going to summer camp as a kid helped him get experience and comfort…Continue reading ➞ Episode Fifteen – Tyler Gildin, Elite Daily

This week’s guest is Jason Horowitz, studio host for Westwood One, talk show host with SiriusXM and play-by-play guy in a number of places. He does a lot.  Here’s some of the stuff we talked about: Jason describes the experience that was seeing “Bayside! The Musical!” (1:23), the wonder that is Kelly Kapowski, despite her…Continue reading ➞ Episode Fourteen – Jason Horowitz, Westwood One and SiriusXM

This week’s guest is Aaron Goldfarb, author of three novels and five books in total as well as contributing writer for a number of publications including Esquire and The Daily Beast. Here’s some of the stuff we talked about: how has getting married impacted the sort of fiction he’ll write going forward (1:46), writing about things…Continue reading ➞ Episode Thirteen – Aaron Goldfarb, Author & Writer

This week’s guest is Zach Berman, Eagles beat writer for the Philadelphia Inquirer. Here’s some of the stuff we talked about: is this as bad as it’s ever been for Philly sports teams? (1:29), the growth in demand for NFL content in the offseason and how fans now care as much about the business of sport…Continue reading ➞ Episode Twelve – Zach Berman, Philadelphia Inquirer

This week’s guest is WFAN and CBS Sports Radio talk show host John Jastremski. Here’s some of the stuff we talked about: how on Earth he maintains that upbeat attitude for his real life and radio life (1:41), the honest importance of being true to yourself on the radio (2:38), how he thinks he’d do…Continue reading ➞ Episode Eleven – John Jastremski

This week’s guest is Mark Medina, beat writer covering the Los Angeles Lakers for the L.A. Daily News. Here’s some of the stuff we talked about: dealing with annoying/hating/trolling/critiquing fans (1:57), what it’s been like to go from living in Pennsylvania and Syracuse to Manhattan Beach (3:02), why neither of us really miss Syracuse–the place,…Continue reading ➞ Episode Ten – Mark Medina, Lakers Beat Writer for L.A. Daily News

The guest this week is Sarina Morales of ESPN’s SportsCenter: AM. Here’s some of the stuff we talked about: her absolutely bonkers sleep/life schedule now that she’s on a national TV show from 7 to 10 AM every day (1:47), Sarina and I debate why ANYONE uses SnapChat—hint, she’s in favor of it (4:29), what…Continue reading ➞ Episode Nine – Sarina Morales, ESPN’s SportsCenter

Zach Schonbrun, contributing sports and business writer for the New York Times, is the guest this week. Here’s some of the stuff we talked about: is the Times just trying to piss me off with N.B.A and Mr/Mrs’ing everyone? (1:30), my one shining moment at Syracuse–the SU Media Game wherein I destroyed Zach’s ankles and…Continue reading ➞ Episode Eight – Zach Schonbrun, New York Times

Jordan Bernfield, ESPN play-by-play guy and host/anchor at 670 The Score in Chicago, is the guest this week. Here’s some of the stuff we talked about: the weirdest part of being an engaged couple (1:53), the many name-related stages of a relationship (4:47), how the industry nowadays is such that you basically have to do…Continue reading ➞ Episode Seven – Jordan Bernfield, ESPN & 670 The Score