The podcast episodes provided explore how traditional gender roles and perspectives on masculinity surface in various discussions, from dating and relationships to broader sociocultural commentary.

For example, the episode 'Ep 491 - Who Piped Carl Winslow ? (feat. James Mccann, Lemaire Lee, & Shawn Gardini)' touches on the topic in the context of discussions about celebrities' personal lives and media's impact. The episode '823: The Question Trap' examines how certain questions can reflect assumptions about traditional gender roles, especially in same-sex relationships.

The episode 'S2 Ep. 9: Dollars & Dating: "The Cost of Loving?"' delves deeper into the cultural influences on gender roles and expectations of masculinity, particularly related to being a provider. Lastly, the episode 'He Cared About Me, So I Broke Up With Him' confronts traditional masculine gender roles by highlighting a man's willingness to be vulnerable and consistently caring in a relationship.