Kai Madison Trump, Charlie Woods and Sam Alexis Woods attend the Benjamin School in Florida. Donald Trump Jr. and Bettina Anderson made it “Instagram official” on Super Bowl Sunday 2025. Dating rumors for Vanessa Trump and Tiger Woods surfaced March 14, 2025, ahead of St. Patrick’s Day.

Rachel Uchitel, who made headlines in 2009 as one of then-married Tiger Woods’ mistresses, recently announced her engagement to security businessman Dan Donovan. In a March 28 Instagram post featuring pictures of the beachside proposal and massive emerald-cut diamond,

Ivanka, who was Vanessa’s sister-in-law when she was married to her brother, Don Jr., rushed to the comments section of Woods’ post Sunday night.