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This is a very easy and quick achievement to get. Play as the Gambler, and land on your opponent's space. To do this you can use some your ability Reduce the Odds to increase or decrease the number on the die if you need to, spending an amount of Fate points equal to the amount you change the result on the die. Make sure you have at least one Fate point left, though. You start with enough Fate points that this shouldn't be a problem.

When you land on their space, choose to Encounter the Character. Then, with at least 1 Fate point left, you can choose the option to Tempt Fate. Doing so means both characters roll dice against each other, and the higher roll wins. No matter who wins though, the achievement unlocks!