Jonathan Gregg on Overcoming Toxic Masculinity & Redefining Manhood

About this episode

Jonathan Gregg discusses modern masculinity, vulnerability, and the impact of fatherhood on his understanding of love and identity.

What does modern masculinity actually look like? For this week’s guest, Jonathan Gregg, it looks a lot like vulnerability, feeling secure in yourself, and a willingness to question the roles we’ve been taught to play. In this episode of Love, Take Two , Jonathan reflects on growing up in a conservative Southern environment and how those early experiences shaped his understanding of identity, relationships, and masculinity. From childhood expectations to adulthood friendships, he shares how questioning those norms helped him build a more expansive view of what it means to be a man. Jonathan’s career has taken him through theater, television, and digital media, appearing in projects like The Blacklist , Blindspot , and Hightown . But beyond acting, he’s become known for candid conversations about friendship, fatherhood, and the complicated ways masculinity shows up in everyday life. Jonathan opens up about the importance of emotionally honest friendships, how fatherhood has reshaped his perspective on love, and why expanding the definition of masculinity benefits everyone. Key Takeaways Growing up in the South and how it shaped Jonathan’s understanding of masculinity Why male…

People in this episode

Hosts: José Rolón, Jaimie Kelton

Guest: Jonathan Gregg

Topics covered

• toxic masculinity
• vulnerability
• male friendship
• fatherhood
• identity
• gender roles

Keywords

• masculinity
• vulnerability
• friendship
• fatherhood
• identity
• gender roles
• emotional honesty

Mentioned in this episode

Books & works: The Blacklist, Blindspot, Hightown

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