As one of the most beloved personalities on Today, Dylan Dreyer excels at juggling early-morning call times, weather coverage, and live television. But her most challenging — and most rewarding — role takes place off-camera: being mom to three energetic little boys. Together with her husband, Brian Fichera, Dylan is raising Calvin, Oliver, and Russell in New York City, where the chaos, laughs, and sibling adventures never stop. And right at the center of it all is Oliver, her spirited second child, whose personality has become a joyful highlight of Dylan’s life.
Born in January 2020, Oliver arrived just weeks before the world shut down due to the pandemic — meaning his earliest milestones happened at home, surrounded by family, cameras, and the constant giggles of his big brother. By the time Baby Russell joined the family in September 2021, Oliver had officially stepped into the role of the middle child — a transition that Dylan openly admits hasn’t always been smooth.
“He’s adjusting,” she joked on Today shortly after Russell’s birth, laughing as only a mom of boys can. “He doesn’t really understand the word gentle yet. There’s a lot of jumping on the couch. We have to keep the baby away from the couch, or else he’s just going to get stepped on.” It was a humorous glimpse into real family life — no filters, no perfection — just three brothers learning how to share space, parents, and attention.
Even Oliver’s name carries a charming story. Dylan once revealed that the name wasn’t selected from a favorite movie or passed-down family tradition — it was chosen after a simple errand. The couple had visited a storefront called Oliver Brown while picking up Brian’s suit one afternoon, and suddenly the name felt unmistakably right. “There were just all these signs,” Dylan said. “We were like, ‘Yeah, I think Oliver’s it.’”
Despite being the middle child, Oliver has never been one to fade into the background. Al Roker was among the first outside the immediate family to meet him, smiling as he held the tiny newborn during one of those heart-melting backstage visits at Today. It was one of many early moments that showed just how loved Oliver already was by the extended Today family.
From there, his big personality quickly began shining through. On his very first Halloween, the family dressed up as astronauts — a theme that perfectly captured the sense of adventure Oliver brings wherever he goes. Space helmets and star-patterned costumes made for adorable photos, and even more adorable memories.
Before long, Oliver was hitting milestones faster than anyone expected. By June 2021, he had officially “graduated” from his highchair and claimed a seat at the big-boy table — a moment Dylan celebrated on Instagram with the unmistakable pride only a mama can show. And in the kitchen, he continued surprising his parents. In August 2022, Dylan couldn’t help but brag when Oliver assembled his own lunch — a small but mighty accomplishment that proved he was already determined to do things independently.
The pride works both ways, though — Oliver has also become one of his mom’s biggest cheerleaders. In November 2022, he was photographed clutching her children’s book, Misty the Cloud: Friends Through Rain or Shine, with a look that said everything: That’s my mom. She made this. It was one of those tender, everyday snapshots that perfectly captures the heart of parenthood.
By January 2023, Oliver was turning three — an age filled with curiosity, dancing feet, and belly laughs. Dylan’s birthday tribute reflected the full wonder of raising a boy like him: “You’ve been singing and dancing to your own tune since the day you were born,” she wrote. “You bring so much joy and love to our lives … Thank you for being you!” The photos showed a grinning little boy celebrating the day in style — exactly the way he lives every moment.
And, in true Dreyer-Fichera fashion, even the half birthdays get a little celebration. Just ahead of July 4th one year, Dylan attempted to surprise Oliver with a special candle — only to discover it was more like an indoor firework. The moment quickly turned from festive to hilarious, giving the family yet another story they’ll laugh about for years.
Life at home with three boys may be noisy and unpredictable — bedtime included — but Dylan wouldn’t have it any other way. The brothers share one bedroom in their New York City apartment, turning nighttime into giggle-filled bonding sessions and secret storytelling hours. It’s a reminder that sometimes the smallest spaces create the biggest love.
As Oliver continues to grow, fans have been able to watch his personality unfold — from baby snuggles to big-kid achievements. He is playful. He is bold. He is always dancing and climbing. And above all, he is adored. Whether he’s sneaking into the frame during a Today interview, helping his mom bake cupcakes, or cheering on his older brother, Oliver is proof that the middle spot can be the most magical place in a family.
Dylan often emphasizes how grateful she is for the life she shares with her boys. Motherhood hasn’t slowed her down — if anything, it has made her world happier, louder, and brighter. And with Oliver right there in the center, keeping everyone on their toes, the laughter never stops.
Because in the Dreyer-Fichera home, three little boys are building a lifelong brotherhood — and Oliver has already mastered the role of joyful ringleader.
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