CCC Presents: Dear Caddie

🔹 Win a Cutter & Buck Quarter Zip with the NFL logo of your choice! Simply submit a Dear Caddie letter (see below for details) and we will choose a winner and feature their Dear Caddie letter at the end of next week’s story! Good luck!

Meet Dear Caddie

He’s not a psychologist. He’s not a therapist. He doesn’t even have a license to give advice - unless you count forty years of carrying other people’s bags, listening to their excuses and watching them self-destruct on the back nine.

From inside the ropes, he’s seen it all: marriages unravel between missed putts, affairs whispered on cart rides and more midlife crises than a Palm Springs plastic surgeon. He’s witnessed balls lost in the weeds, dignity lost in the bunkers and heard more confessions than a priest in South Boston.

Dear Caddie doesn’t read books - he reads greens, scorecards and body language. He’s the man in the flat cap with the calloused hands and the deadpan stare, and if wisdom comes from pain, he’s looped through enough of yours to qualify.

So when you write Dear Caddie, remember: he’s not here to sugarcoat the read. He’s here to tell you the truth - even if it stings worse than a shanked iron on a cold early morning tee time.

Suspicious in Scottsdale

Dear Caddie,
I'm pretty sure one of the guys in my regular Saturday foursome is shaving strokes. Nothing major - just a 7 that becomes a 6 here and there. But over 18 holes it adds up, and he's been winning our Nassau bets for three months straight. Do I call him out or let it slide?
— Suspicious in Scottsdale

Dear Suspicious,
You already know he's cheating, you just want permission to say something. So here it is: yes, call him out. But do it smart. Don't accuse him on the course - that's how fistfights start and memberships end. Pull him aside after the round, tell him you've noticed the math doesn’t add up, and suggest everyone double-check their cards before signing. If he's got any shame left, he'll clean it up. If not, you've got a decision: keep playing with a cheat or find a new Saturday group. Either way, stop funding his dishonesty with your Nassau money - cheats don’t change, they just move tees.

Fairway Frank

Dear Caddie,
My wife says I play too much golf. I'm out there every Saturday and Sunday, plus one twilight round during the week. She says the kids barely see me and I'm "choosing golf over family." But I work 60 hours a week - don’t I deserve some time to myself? Am I the bad guy here?
— Fairway Frank

Dear Frank,
Let me translate what your wife actually said: “You're never home and the kids are growing up without you.” And you heard: “Stop having fun.” Those aren't the same thing, Frank. Nobody's saying you can't play golf - they’re saying 30-plus hours a week on the course while working 60 leaves about ten minutes for the people who actually live with you.

Here’s a radical idea: cut it to one weekend round and that twilight. Spend the other day with your family. Because here’s the thing about kids - they don’t give mulligans.

Broke in Boca

Dear Caddie,
I can't really afford my club membership anymore - business took a hit last year and money's tight. But I've been a member for eight years and all my friends are there. I'm embarrassed to quit. What do I do?
— Broke in Boca

Dear Broke,
Pride's expensive, and right now you're paying double - once for the membership you can't afford, and once for the stress of pretending everything’s fine. Here's the truth nobody wants to say out loud: your real friends won’t care if you're a member. They'll still grab lunch with you, still invite you as a guest when they can. The ones who ghost you when you resign? They were networking contacts, not friends.

Take a break, get your finances sorted, and come back when you can afford it without eating ramen three nights a week. The course will still be there - and half your foursome is one bad quarter away from joining you.

Cut and Confused

Dear Caddie,
I got uninvited from my regular Thursday game and nobody will tell me why. I've asked around and everyone just says “it wasn’t personal” or changes the subject. What did I do wrong?
— Cut and Confused

Dear Confused,
When everyone suddenly gets amnesia about why you're out, it means one of two things: you did something so obvious they can't believe you don’t know, or you didn’t do anything and someone just doesn’t like you. Think back - were you slow? Loud? Giving everyone swing tips they didn’t ask for? Constantly on your phone? Any of those could do it.

But here’s the hard truth: if nobody’s willing to tell you straight, they’ve already decided you’re not worth the awkward conversation. You can keep begging for answers or you can find a new group that actually wants you there. I’d pick door number two - life’s too short to play golf with people who ghost you without explanation.

Got a problem that only Dear Caddie can solve? Click HERE or email us at [email protected] - anonymity guaranteed, brutal honesty promised!

Poll Question

Last Week's Poll Result

What’s the real lesson of Cartastrophe?

🟩🟩🟩🟩🟩🟩 You can’t fix stupid, but you can fence it off

🟨🟨🟨⬜️⬜️⬜️ If it moves, someone will crash it

🟨🟨🟨⬜️⬜️⬜️ The cart is innocent, but the member rarely is

🟨⬜️⬜️⬜️⬜️⬜️ You can't make par from the ER

There were a lot of lessons in Cartastrophe! but we agree that fencing off stupid is probably the best all-around bet. Relying on the self-education of the masses is a fool’s errand, and certainly not something that golf courses should do when considering carts and cliffs!

By the way, if you are a newer subscriber, don’t forget to catch up on past stories at ccconfidential.vip - and while you’re at it, tell a friend!