Dylan Dreyer’s holiday season was not without its trials and tribulations. The 44-year-old TODAY show anchor shared a very real holiday photo to her 850k Instagram followers on Wednesday, December 31.
Along with adorable snapshots of her Christmas celebrations with her three sons – Calvin, nine, Oliver, five, and Rusty, four – she also shared a photo of her middle son sitting on a hospital bed.
Dylan captioned the post: “A little taste of the holiday…and a little touch of the flu! Hope you all had a wonderful holiday and wishing you a Happy New Year!!” The mom-of-three joined almost 71,000 other New Yorkers who also had the flu during the holidays.
According to the New York State Department of Health, flu activity often peaks between December and February. For parents in similar positions, medical experts at the AAP suggest monitoring for “red flag” symptoms that require a hospital visit, such as labored breathing or inability to keep fluids down.
As the family recovers from their illness, they have a lot to celebrate. Dylan shared photos of her sons opening presents, including sweatbands, puzzles, and more. And a week before Christmas, Dylan’s son Calvin celebrated his ninth birthday!
For Calvin’s big day, Dylan told Sheinelle Jones and Al Roker on the Third Hour of TODAY that she had very specific plans for his birthday cake. She previously explained on social media: “Homemade birthday cakes have really become a thing. The kids put in a request and I try to figure out how to make it happen. Cal’s request this year: a sports cake with 4 sports. Football, golf, hockey, and baseball. Stay tuned!”
© InstagramOliver turns seven tomorrow, January 2, so Dylan is probably preparing his homemade cake. The proud mom is careful when making cakes for her sons. Calvin has celiac disease, which, per the Mayo Clinic, is “an autoimmune condition where the immune system reacts to gluten, sometimes causing damage to the small intestine.”
So, Dylan turned her entire household into a gluten-free one. In fact, she previously even exclusively told HELLO! she has contemplated moving to the UK because the gluten-free market is a lot more expansive. “I think it would be an easy transition if I ever were to go out there [to the UK] and my life revolves around my kids and with Calvin having celiac disease.”
Managing a gluten-free household is a significant undertaking. For parents inspired by Dylan’s journey, the Celiac Disease Foundation recommends strictly avoiding cross-contamination in the kitchen, particularly when baking birthday treats, as even a crumb of gluten can trigger an autoimmune response.
She continued, telling us: “It’s honestly all I think about. All I have to do is feed kids all day long and it’s hard to feed him sometimes. It would just be fun to experiment and try to live there and see how much easier it would be to live with kids there.”
© InstagramDylan’s year of transition
Ending with one of her children in the hospital with the flu was just a cherry on top of a difficult year for Dylan. In July 2025, the 44-year-old announced she was separating from her husband, Brian Fichera, after 12 years of marriage.
“I am incredibly grateful for the support and love you’ve given me through it all. For that reason, I want to share with you that a few months ago, Brian and I made the decision to separate,” she wrote to Instagram.
© InstagramIn November, Dylan and her three boys moved out of New York City to the suburbs. This move highlights a growing trend of “lifestyle relocation” following major family shifts, as parents seek more space and community support during co-parenting transitions.
For many, Dylan’s openness serves as a reminder that even perfect TV lives face the messy realities of health scares and heartbreak. Her resilience in maintaining family traditions like homemade cakes, despite a difficult year, offers a blueprint for other single parents navigating their first holiday season post-separation.
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