Lots of great answers here, its interesting to see who people are interested in. So many good choices out there. I think any of them would be amazing to get that kind of experience. Id have to pick Rory, he is just impressive.

Tiger or Rory. I got to meet Lee Trevino at the Greenbrier a few years ago, really nice guy!

The easy choice is Tiger but I think I would probably enjoy playing with Max, JT or Rickie more. Picking just one would be Max. Just watch the Bob Does Sports vs Max videos on Youtube.

Keegan Bradley.

Lee Trevino for me! Even Tiger makes it a point to talk golf swing with the Merry Mex when he gets a chance!

Nelly Korda I think would be learning time and nice relaxing fun time.

John Daly!

Mr Jordan Spieth for sure.

Freddy would be my first choice, but if I got invited to fill out a foursome with Justin/Jordan/Rickie, I'd be on a plane within a couple hours!

I spent my HS and college summers as a caddie at a local private club back in the late 80s/early 90s. I was privileged to be able to caddie for some names that are still pretty big at an annual charity pro-am where every group played 9 with a tour pro and 9 with a local club pro. Favorite loop was definitely Brad Faxon, but carrying for Nick Price and Steve Elkington twice apiece was great as well. Wasn't my loop, but we even had Lee Janzen the day after he won the US Open in 1993 - and yes, he brought the trophy and put it on the first tee for all to see!

Tommy Fleetwood is my choice! Just seems like a cool guy to talk life/golf with.