As I wrote back in February, if you fancy yourself a competitive golfer, then you simply have to be playing for money on the course. Whether it’s $1, $5 or $10-10-20, it has to be an amount that makes that six-foot, downhill right-to-left slider mean something. For some, it’s a much larger sum, which I do not recommend amongst friends. That said, it should be an amount that makes you feel nerves over that tricky tee shot or greenside chip. Something that gets the juices flowing. It’s good for you. Feeling pressure means you’re still human in a world that increasingly tries to make everyone feel like a robot.

The most human feeling of all, ideally, is taking money from a close friend and putting it in your pocket. Unfortunately, in the Venmo society we live in, it’s rare you’re actually exchanging cash after a round of golf. While that’s always the preferable method in a literal “money game,” Venmo, and other apps like it, in theory, make it incredibly easy to square up debts after the round. And honestly, the “$5, Golf L” notificaiton hits just as nice as a crisp Abe Lincoln.

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And yet, even when it’s never been easier to settle debts, some folks still seem to find a way to not pay up on time. Sometimes not at all.

I’m not naming names, and I’ve strategically saved this subject to write about long after the last time I recall this happening to me. So, if anybody who I’ve played with fairly recently reads this and suspects it’s them, it’s not. It could be literally anyone I’ve played with in my life. Chess, not checkers.

How do you handle this type of person/situation? The “welcher,” for lack of a better term. The tricky part is, it’s almost always over a very small sum, which is what the majority of recreational golfers are playing for on the weekends. Five bucks. Twenty bucks. Maybe with junk and some other side games, it’s $40 or $50, tops. Amounts you should not have to shake anybody down for. It’s almost more embarrassing for you to be asking for the $5 or the $10 you won than it is for the person not forking it over right away. It’s a tightrope act.

Mind you, I totally understand being somewhat “forgetful.” I’ve had situations where someone owes $5 after the round, forgets, and then the next time we play, weeks or months later, says “don’t I still owe you?” I respect that. It’s not my style, but at least they didn’t memory-hole it.

The real problem becomes when it’s the same person, or people, over and over. You play with them a lot, always for money, and any time you lose, you settle the debt instantly over a beer afterward. Anytime you win, though, this person’s “gotta run” and you’re not seeing that money for days, weeks, if at all. Again, it makes you look small to send a text three days later “hey, got my $10?” But it also makes you look like a total sucker to cough it up every time you lose and never see a cent any time you win.

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Is it as simple as just putting the loser (not derogatory) in question on the spot after the round? Do you send a Venmo request and risk looking like a cheap-o who desperately needs the $10? Do you go full passive aggressive and drop a “guess I’m never seeing that $$$” right after catching the dub? Do you remind the person the next time you lose that they owe you and now you’re all square, indicating that debt has been on your mind the entire time?

Those are all decent options, but I think the prudent move is to cut this person off. Not from playing with them, but from playing with them for money. If they stiff you enough times, make it known the next time you’re on the first tee that you’re happy to play a friendly game, but you’re not putting anything on the line. When this person balks, be honest with them. You tell them they never pay up, so you don’t feel like risking money you have no chance of receiving and a high chance of losing. That should set them straight. And if they suddenly want to pay up all their debts while simultaneously making you feel like the bad guy for daring to ask for them, you should refuse and be the bigger person. No more $$ games, pal, you can’t handle them.

Another option that may avoid this big-time headache is, especially if you have a regular playing partner, keep a year-long running tab in your notes app on your phone. By the end of the year it could very well end up being a total wash. Or, you’ll have won or lost a large enough sum that needs to be settled. Not to mention the fact it would be fun to follow for both parties all season, and it gives the potential loser an idea of what he’ll need from the ATM when the calendar turns to Jan. 1. Or how large of a missile the Venmo request notification is going to be.

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).

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This article was originally published on golfdigest.com