The Holidays Are Hard: How to Cope, Connect, & Set Boundaries

In this special holiday episode of First Round’s On Me, Joey and Hannah talk about the side of the holidays that rarely makes it into movies or Instagram posts — the heaviness, the distance, the awkward questions, and the quiet loneliness so many people feel this time of year.They open up about fractured family dynamics, spending Christmas alone, navigating intrusive questions about marriage and children, and the grief that comes not from loss — but from disconnection. This conversation is for anyone who doesn’t feel at home during the holidays, anyone returning to complicated family environments, and anyone trying to protect their peace while still craving connection.The episode explores how to set boundaries without blowing things up, why lowering expectations can save your mental health, and how chosen family can be just as meaningful as the family you’re born into. They also talk about creating new traditions, being vulnerable enough to ask for connection, and finding ways to make the holidays meaningful — even if they don’t look “perfect.”If the season feels heavy, this episode is here to remind you: you’re not broken, you’re not alone, and you’re allowed to do the holidays your own way.💬 In the comments: How do the holidays really feel for you this year?00:00 – Holiday pressure & intrusive family questions01:00 – Why the holidays are hard for so many people 03:00 – Different relationships with family & Christmas05:30 – Growing up with big family traditions07:00 – Spending Christmas alone & creating new traditions09:00 – Reframing loneliness during the holidays11:00 – Going home to difficult family dynamics13:00 – Boundaries vs. keeping the peace15:00 – Lowering expectations to protect your mental health17:00 – Chosen family & adult connection19:00 – Being vulnerable & asking for connection21:00 – Using FROME to meet friends, not just dates23:00 – Small gestures that create meaningful memories25:00 – Being present with parents & grandparents27:00 – Creating new traditions with your own family28:00 – Final reflections & holiday message