John Daly has never been just another golfer. From outdriving Tiger Woods while hungover to lighting up crowds with his wild outfits and on-course banter, the 2-time major champion has delivered some of golf’s unforgettable moments.

But these days, the 59-year-old is a bit tender on the greens. Daly withdrew from the Regions Tradition in May due to injury and finished T63 at the Kaulig Championship last month.

While his play on the PGA Tour Champions is rocky, his love life is certainly not.

Daly, who has been in a relationship with Anna Cladakis since 2007, took a heartfelt step forward in their long-standing romance this weekend.

On Saturday, he posted a birthday message for Anna’s daughter, Charitsa Cladakis, typing, “Happiest Bday to my bonus daughter…. LIL GRIT!”

He followed it up with a proud nod to her future, “You’re going to be one amazing Dr! I love you! Happy 21st!”

And no doubt the message had what one can say John Daly vibes. “Time to toast a @goodboyvodka @charistaa.” (Good Boy Vodka is Daly’s own vodka brand, which he co-founded in 2021)

Charitsa is Anna’s daughter from her previous relationship with Chris T. Sullivan, the founder of Outback Steakhouse. And her 21st birthday just showcased Daly’s deepening bond with Anna’s family. Especially the two words “bonus daughter!”

That’s a notable shift for a man whose personal life has often been turbulent. Daly has been married four times.

First to Dale Crafton (1987–1990), then he was with Bettye Fulford (1992–1995), followed by Paulette Dean (1995–1999), and Sherrie Miller (2001–2007).

His relationships were often marred by public disputes, legal battles, and personal struggles. His fourth marriage ended after a highly publicized altercation, and Daly was later granted custody of their son, John Daly II.

But with Anna, things have been different. In a 2016 interview, Daly credited her with bringing calm to his chaotic world.

“Anna has been one of the most supportive human beings in my world,” he said.

The couple hasn’t tied the knot, yet their nearly two-decade relationship has endured more than most marriages. Maybe that is how it was meant to be.

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