‘Today’s Dylan Dreyer Celebrates Son Oliver’s Major Childhood Milestone

Dylan Dreyer had a proud mom moment over the weekend.
While enjoying a sunny day outside with her three sons, Dreyer’s middle child, 5-year-old Oliver, reached a fun childhood milestone: ditching his bike’s training wheels. “Proud momma alert!!! Yay Ollie!!!” the Today host captioned an Instagram clip of Oliver showing off his new skill on Sunday, September 14. “2 wheels…no turning back now!!”
Dreyer filmed the heartwarming moment while enjoying a sunny day outside with her three sons, including 8-year-old Calvin and 3-year-old Rusty. (Dreyer shared her kids with her estranged husband, Brian Fichera.)
“Yes, Ollie!” she exclaimed in the clip. “Keep going! Keep going! Pedal, pedal, pedal!” Dreyer gave her son a congratulatory high five, while big brother Calvin encouraged his brother to “do that again, bro, one more time.” Rusty, meanwhile, enjoyed riding his own bike with training wheels.
Fan shared in Dreyer’s excitement in the post’s comments. “Yippee!!! Way to handle that bike, Ollie!! Ride Ollie Ride!!! 👏👏👏👏😍❤️,” one user wrote, while another added, “They have grown so fast. Way to go Ollie.👏👏👏.”
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“He’s such an adorable little dude! ❤️,” a different fan gushed. Someone else also praised Calvin for being “such a great, supportive big brother.”
Dreyer followed-up Oliver’s accomplishment by attending her Today colleague Craig Melvin‘s annual Bottoms Up Invitational. The event kicked off with a fundraising concert for the Colorectal Cancer Alliance on Sunday, followed by a golf tournament on Monday, September 15.
Before hitting the green, Dreyer appeared on the third hour of Today from Norwalk, Connecticut, with Melvin, his wife, Lindsay Czarniak, and Sunday Today‘s Willie Geist. “Every year, the idea is simple. We raise money, raise awareness for the Colorectal Cancer Alliance,” Melvin shared on the show. “And last night, this morning, we raised $1.133 million, which is the most we’ve ever raised. So, good friends make it possible.”
Dreyer, for her part, said she talked with people on Sunday who were inspired by the event to get tested for colorectal cancer. “It’s exactly doing what it needs to do,” she stated. “It’s raising awareness so that folks get tested, so that they can be treated if, God forbid, they have it. They can be treated before it’s too late.”
On the show, Dreyer recalled how she and her team won last year’s Bottoms Up Invitational tournament. “I am the reigning champion from last year,” she jokingly bragged. “I don’t know how the numbers worked out. Your friends were in charge of the numbers, and I was just along for the ride.
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