Debating Jillian Michaels and Winning with Tigress Osborn episode artwork

EPISODE · Mar 26, 2026 · 1H 20M

Debating Jillian Michaels and Winning with Tigress Osborn

from Making It Awkward · host Jessica Wilson

Tigress Osborn debated Jillian Michaels about the health and wellness field on Jubilee Media's Surrounded–and won! Tigress, the Executive Director of NAAFA, comes back to the show to talk about her experience being one of (supposedly) 20 body positivity activists to debate Jillian. The two talk about her experiences including the production and editing of the show, how she ended up in one of the 20 seats, what it's like to sit across from Jillian, how Jillian likely knew who Tigress was before she sat down, and what she would have liked to have discussed with Jillian if given the chance. Tigress also shares critiques she may get for being on the show, and the two discuss whether or not to fact check Jillian on social media.    Events at NAAFA NAAFA's campaign for size freedom NAAFA blog Fat bias in news media Jillian part 1 episode Marcy x Jillian follow up episode Zane and his weight release Like this episode? You can rate, review, subscribe, follow, share and comment! Questions about the show? Guest pitches? Email [email protected] You can buy awkward merch! You can become a Patreon member! You can watch this episode at https://www.youtube.com/@MakingItAwkwardPod Follow Jessica Wilson on Instagram @jessicawilson.msrd and TikTok @byjessicawilson   Jessica Wilson's book: It's Always Been Ours; Rewriting the Story of Black Women's Bodies   

Episode metadata supplied by the publisher feed · Published Mar 26, 2026

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Debating Jillian Michaels and Winning with Tigress Osborn

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