Dylan Dreyer’s Latest Family Update During Her Break From TODAY Has Fans Smiling After She Admitted It “Took A Few Tries” To Finally Pull Off The Moment She’d Been Hoping For. Away from the pressure of live television, the beloved TODAY star shared a refreshingly candid glimpse into family life, proving that even the simplest victories can come with unexpected challenges. The heartfelt update is quickly winning over fans, who say it’s another reminder that Dylan’s most meaningful moments happen long after the cameras stop rolling.

Dylan Dreyer shares new family update during break from Today: 'Took a few tries'

Dylan Dreyer has been enjoying her days off, away from her demandingToday show schedule.

The star recently shared a hilarious video of her sons Calvin, born in 2016, Oliver, born in 2020, and Rusty, born in 2021 swimming in a hotel pool.

The-mother-of-three, who’s been absent from the show this week, desperately tried to get a picture of the trio in a new video, as she desperately called out to get their attention.

She was can comically be heard in the online video requesting: “Guys please. Guys, one picture. Just one. Please. There we go – Oli’s cute,” right before one of the brother’s pulled him into the water.

Dylan yelled out “guys,” and Oli screamed: “Stop fighting,” as he posed once again for the sibling picture. She joked in her caption, writing: “Took a few tries but we got there!”

Dylan shared pictures from her famiy vacation

Dylan shared pictures from her family vacation (Instagram)

Fans react

Laura Jarrett commented: “So. Many. Tries.” One person joked: “I think you are great but [there’s] two sides to every story.” Another follower continued: “I wouldn’t disrupt those lion cubs while playing.”

One fan commented: “They are adorable. I sure miss these days with my boys, who are 40, 33, and 28. Keep enjoying these moments.”

In another post, Dylan shared a carousel of herself painting her nails out on the dock by her sons, with the overlaid text: “If you want to live dangerously, paint your toenails surrounded by boys.”

The second picture showed her sons being grossed out while they devoured their ice creams. Dylan captioned the post: “Wild decision…”

The star as absent from the daytime show this week

The star was absent from the daytime show this week (Instagram)

Dylan’s take on parenting

Dylan got separated from her husband of 12 years, Brian Fichera last July. She officially filed for divorce in March 2026.

When the TV star served as a guest so-host on Today with Jenna & Friends in November, she got candid about how she shared the family news with her little ones.

Dylan is a doting mother to three boys

Dylan is a doting mother to three boys (Instagram)

She recalled: “I asked Calvin. I said, ‘What do you think a family is?’ And he said, ‘Well, it’s a group of people that love each other.’ And I said, ‘That’s what we are. And we will always be that for you.'”

Dylan explained: “‘But Mommy and Daddy work better as friends than as husband and wife.’ And he doesn’t care about a title. He doesn’t care what we are officially, none of them do. They are surrounded by love every single day.”

Dylan Dreyer and her son Calvin and husband Brian Fichera

The former couple continue to co-parent (Getty Images)

Since then, the former couple have continued successfully co-parenting and went on to celebrated Thanksgiving together.

The journalist concluded: “First and foremost, the kids have to feel love and they have to be happy. I have three boys. I want their dad in their lives. They need that. They need both the dynamic of a father and a mother. We’re providing that to them in the best way possible.”a

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