Dylan Dreyer’s holiday season looked joyful on the surface — but behind the smiles was a reality few fans expected.
The 44-year-old TODAY show anchor gave her 850,000 Instagram followers an unfiltered glimpse into the highs and lows of Christmas, sharing not only adorable moments with her three sons — Calvin, nine, Oliver, five, and Rusty, four — but also a sobering image of her middle child sitting on a hospital bed. 
Alongside the photos, Dylan wrote:
“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!!”
She later confirmed that Oliver had been struck down by the flu — one of almost 71,000 New Yorkers who fell ill during the festive period, according to the New York State Department of Health, where flu cases typically peak between December and February.
Doctors advise parents to watch for red-flag symptoms such as laboured breathing or the inability to keep fluids down — warning signs that warrant immediate medical attention. 
Despite the scare, Dylan still made sure her boys enjoyed Christmas. She posted snaps of presents being opened — from sweatbands to puzzles — and just a week earlier had been preparing for another family milestone: Calvin’s ninth birthday.
Speaking on the Third Hour of TODAY, she revealed she had a very specific plan for his cake.
“Homemade birthday cakes have really become a thing,” she previously shared. “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 four sports — football, golf, hockey, and baseball.”
As Oliver prepares to turn seven on January 2, Dylan is likely already planning another homemade creation — a careful task, as Calvin has coeliac disease, an autoimmune condition triggered by gluten. To protect him, Dylan has turned her entire household gluten-free, once even revealing she had considered moving to the UK because of its wider range of gluten-free products. 
“It’s honestly all I think about,” she told HELLO!. “All I do is feed kids all day long — and it’s hard sometimes.”
Health experts warn that even a tiny amount of gluten can trigger a reaction, making strict kitchen routines and cross-contamination avoidance essential.
The hospital scare came at the end of an already challenging year. In July 2025, Dylan announced her separation from husband Brian Fichera after 12 years of marriage. By November, she and her sons had moved from New York City to the suburbs — a shift many families make after major life changes.
Her holiday honesty has struck a chord with fans, reminding them that behind the polished TV image is a mother navigating illness, heartbreak and new beginnings — yet still holding onto the magic of homemade cakes and Christmas traditions. 
For many single parents facing their first festive season after separation, Dylan’s story is a powerful reminder: even when life feels messy, resilience can still create moments of joy.
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