This isn't quite what the original post asked for, but still my favorite caddie moment. Like Marc's story, it also occurred in a group with Nigel.
I met Nigel back in July when he happened to be in town around the Fourth. We met up for a round at my club that also included two local friends of mine. One of those friends was my buddy Jack, a 6'5" former college basketball player who probably plays about three rounds of golf a year. He's a really nice, really easygoing, very strong guy who probably would play to about a 37 handicap.
My club runs a very strong Evans' Scholar caddie program, so we picked up four high school kids to caddie for us. Jack had never played with a caddie before, and the caddiemaster matched him up with one of two girl loopers at our club. She's also by far my favorite - a chatty and easygoing teenager with a mess of curly red hair and freckles who, much like Jack, knows very little about golf but approaches the game with a ton of earnestness and enthusiasm.
On the first tee Jack turns to her and asks "So, what's my strategy on this hole?"
"Well, honestly, I don't know a lot about golf," explains the caddie. "But you definitely want to hit out toward the stripey grass and try to get it in the hole fast."
"Awesome!" says Jack, with a real confidence gained from hearing her simple explanation. He then proceeds to snap hook a ball about 120 yards forward and 150 yards left.
Five or six shots later, he's still 160 yards out and on a very steep downslope in thick rough. He turns to his caddie and asks, "You got any advice for how to hit this?"
She smiles the biggest sympathetic smile I've ever seen and says, with an amazing blend of sincerity, optimism, and naivete, "Umm, just keep doing your best!"
I've never seen a better blend of two personalities between caddie and golfer than that day, nor an odder blend physically. A chubby redheaded high schooler and the athletic lawyer towering almost two feet above her, walking the course through four hours of rain and a solid 130 strokes, chewing 10th Tee bars and drinking Gatorade and chatting and smiling the entire time. I'm not a huge fan of caddie golf, but those kids added a lot to the round that day.