How to Win a Bar Bet

There’s nothing in the world like a bang-on bar bet. It is a special kind of magic that surrounds those proposals that one guy (because, let’s face it, no woman would ever engage in such alcohol-fueled buffoonery) issues to another that simply cannot be seen through. How is it, then, that these apparently unachievable challenges so often find their mark? Surely the biggest obstacle to scoring a bar-bet victory is in identifying the victim who’ll take you up on your proposition.

One school of thought advances the idea that many bar bet dupes take the bet knowing they’re going to lose; their interest in how it’ll go down trumps their monetary losses. 

In any case, it generally begins with a scam artist making a loud and public claim that attracts attention, some of it bleary eyed, from the assembled masses. 

“I’ll bet I can tie this cigarette in a knot without breaking it,” he might announce. Or: “I’ve got $20 that says I can blow the bottlecap back into the bottle.” And so on.

Here’s where the real trick comes in. Clever hustlers understand the importance of engineering the proposal such that it looks like the chump’s holding the reins. This means introducing an idea in a roundabout way, without ever copping to an opinion about it. Perhaps the guy “discovers” one of the bet’s key props, and makes a seemingly off-the-cuff — but highly provocative — statement in response to it. Maybe he’s got a buddy in the crowd who can aid and abet. 

In any case, the aim at this point becomes to get the mark to galvanize his point of view, even as the perpetrator makes no sudden moves to embrace his. Eventually, in theory, it’s the dupe who digs in, almost insisting that the mastermind enter into a wager.

And this is when the instigator must go in for the kill. And if the shill tries to back down, his opponent needs to work all the angles to draw him back. It’s key here to make the guy feel like he’s doing you a favour by taking on your overture. And don’t be above shaming him. Victory’s going to taste sweet — no matter how the dish was delivered to the table.