Today Show meteorologist and fan-favorite Dylan Dreyer shared an emotional update that moved many of her followers to tears. In a heartfelt Instagram post, Dylan opened up about losing someone deeply important to her family—former MLB star Tim Wakefield—revealing how his absence hit her unexpectedly during a special moment at the Hilton Grand Vacations Tournament of Champions golf competition.
Dylan posted a video of herself taking a swing on the course during the tournament. The shot carried far more emotional weight than a typical highlight: her golf ball landed within ten feet of the 18th hole, a hole dedicated in tribute to Wakefield. In her caption, Dylan explained that both she and her husband, Brian Fichera, immediately welled up with tears as they realized how meaningful that moment felt. Wakefield, a close family friend and beloved figure in their lives, passed away only months before. Dylan wrote, “We lost our dear friend #timwakefield. They honored him with his number on hole 18… Brian and I had tears in our eyes when my ball landed within 10 feet. We miss you every day, Wake.”
Dylan and Brian, both avid golfers, have been part of the tournament for years. The event pairs LPGA pros with celebrities and athletes, and Brian serves as Dylan’s caddy—something she has described as a joyful and grounding experience. Speaking previously to HELLO!, she shared that Brian is “truly my biggest fan,” someone who can instantly lift her confidence or pull her out of a frustrating round. Their dynamic on the course reflects the closeness of their relationship off-camera.
That deep connection extends into their home life as well. Dylan and Brian, who became popular on social media for their humorous, down-to-earth family posts, raise their three young sons—Calvin, Oliver, and Russell—in a cozy two-bedroom New York City apartment. Despite the limited space, Dylan has repeatedly expressed how much she loves parenthood, even admitting she wishes she had started having children earlier. Although fans often ask whether she plans to expand her family, Dylan has said she feels “maxed out”—yet incredibly fulfilled—with her three boys.
A charming contrast to city living, the family also spends weekends and holidays at their beachside home just outside the city. The kids enjoy endless outdoor playtime, while Dylan and Brian find the change of pace rejuvenating.
Throughout the years, Dylan has been open about the joys and challenges of motherhood, marriage, and her demanding TV career. Yet this latest post showed a more intimate layer of vulnerability. The tribute to Wakefield highlighted the depth of her friendships and how profoundly she feels moments of loss.
As fans flooded her comments with love and condolences, it became clear that Dylan’s story resonated far beyond golf or grief—it was a reminder of how unexpected moments can connect us to those we’ve lost, and how small, beautiful coincidences can become powerful symbols of remembrance.
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