Recently, I had to fork over the most amount of money that I have ever lost on the golf course. To be clear, it is not an amount that is going to put me out on the street with a beggar’s cup. I did not have to dip in my savings. I’m going to be able to pay all of my bills this month (though I really wish I had the extra $7 now for the “Penguin” visit at my son’s daycare). And the best part? My wife doesn’t read anything I write, so she’s never even going to see this and conduct a Jack Bauer-level interrogation to find out the exact sum. It’s all good in my hood.

But it certainly did get me thinking, how much is too much money to play for on the golf course? For me, the number I parted with was right in the ballpark. But here’s the thing: I agreed to it on the first tee. And in multiple text messages prior to the round. My thought process the entire time was that I was going to win the match and win that amount of money. Because that’s how competitors think. It never occurred to me that losing was an option. 

Unfortunately, it is very much one of the options when you agree to play for money. You might win it, you might lose it, or it might be a total wash. Even if you’re the one getting a boatload of shots, you might lose all of it about six different ways, like I did. It happens. I’d do it again tomorrow. Unless the penguins are coming back to daycare. 

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But the simple fact is that not everyone is comfortable with playing for big money, or any money at all. In my view, though, if you’re not going to put a little something on the line, what the hell are you even doing out there? It doesn’t have to be $50 or $100. It could be $5. It could be $3. It just has to be something that makes the eight-footer matter. An amount that makes it mean something. As one tour pro told me last year when discussing this topic, it’s not even about how much it is, it’s just about taking your buddy’s money and putting it in your pocket. For me, the action IS the juice. 

Of course, members at elite, old money places, or members of the BurnerVerse, would tell you anything over $5, or a classic $5-5-10 Nassau, is gauche. Playing for, say, $50, or going full high-roller status and playing for hundreds or even thousands, is downright classless. All that does is create unnecessary tension amongst friends. Losing large sums like that could be relationship-altering. I can buy all that.

But I’d personally never fault anyone for wanting to up the ante, and I’d never cry poor after the fact if I agreed to it. That’s my overall point here—the entire group has to agree on the amount, and it has to be extremely clear. It actually wasn’t even that clear to me in this recent game, which had about five different games within the game, but I was glad to not be the one keeping score. These were serious golfers, like myself, who keep serious score and a seriously-close eye on every little thing happening in the match. I’ve kept so much score in my life that I love when someone else does and just tells me at the end how much I won or lost, which was the case here. There were matches within matches, junk within junk. I knew what I was getting into, and I actually had a great stretch on the final six or seven holes that cut into my losses. That’s right, I was on track to lose even more, but myself and my partner were able to save some face and make it a lot less painful. 

Just make sure you set the parameters and everyone knows them on the first hole, and that you know everyone is good for it and you won’t have to shake anybody down. $10-10-20? $20-20-40? $5-5-10? If anyone in the group even hints at the amount being a little too rich for their blood, you should respect their feelings and meet in the middle. Do not, under any circumstances, pressure anyone into playing for more than they want to. While I’m all for being a competitive dog, it is still supposed to be fun and light-hearted. I want to be able to talk a little smack, too. If you’re playing for more than someone wants to, beating them, AND talking smack, that is a recipe for combustion.

Play for a little, play for a lot, I’m game for whatever. Make sure the group is comfortable not only with losing the agreed upon amount, but hearing about it afterward. 

Do you have a “stupid” golf problem? A question you’re too ashamed to ask your close friends? A conundrum that needs to be talked out in a public forum? We’re here to help. If you have etiquette-related inquiries or just want to know how to handle some of the unique on- or off-course situations we all find ourselves in, please let us know. You can email me ([email protected]) or send me a DM on Twitter/X (@Cpowers14) or on Instagram (@cpthreeve).

This article was originally published on golfdigest.com