Josh & Hailee Are Having a Baby, the Chiefs Dynasty is Dead, and End of Year Awards ft. Olivia Culpo

Josh Allen and Hailee Steinfeld are expecting their first child together. Hailee shared the news in her “Beau Society” newsletter. But Josh Allen kinda gave it away with his empathic morning sickness on the sidelines. We wrap the last episode of the year with our annual Wellies, including categories like “Most Exhausted PR Team” and “Diva of the Year.” Disagree with the nominees? Sound off in the comments. In this episode of Well Played, we also cover: An update on the Sherrone Moore case out of the University of Michigan Why motherhood made Olivia Culpo mourn who she was before having her baby How Ann Michael Maye’s “Bakemas” killed Drake Maye’s win Why we’re not surprised A’ja Wilson is a co-chair for the Met Gala’s host committee Introducing the greenest flag in college football, Fernando Mendoza Thanks to our presenting sponsor Capital One Venture X Business Card! Visit ⁠ to learn more. Well Played will be on winter break for the next few weeks. Until then – thank you for all of the support in 2025. This show would be nothing without you! See you in the New Year, love you mean it byeeeeeeee! - Blake & Caroline Follow Olivia Culpo on IG: @oliviaculpo Follow Olivia Culpo on TikTok: @oliviadangerculpo Follow Blake on IG: @blaaakkkke Follow Caroline on IG: @cghendy Follow theSkimm on IG: @theskimm Learn more about your ad choices. Visit megaphone.fm/adchoices

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Josh & Hailee Are Having a Baby, the Chiefs Dynasty is Dead, and End of Year Awards ft. Olivia Culpo is an episode from Skimm This by theSkimm.

This episode is 81:50 long.

This episode was published on Dec 17, 2025.

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