heads or tails

American  

noun

1. a gambling game in which a coin is tossed, the winner being the player who guesses which side of the coin will face up when it lands or is caught.

2. the tossing of a coin in this manner to determine a question or choice.

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heads or tails Idioms  

1. An expression used when tossing a coin to decide between two alternatives, as in Let's just flip a coin to decide who pays—do you want heads or tails? Each person involved chooses a different side of the coin, either “heads” or “tails,” and whichever side lands facing up is considered the winner. This usage, dating from the late 1600s, is sometimes turned into Heads I win, tails you lose, meaning “I win no matter what,” which probably originated in an attempt to deceive someone. [Mid-1800s]

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Etymology

Origin of heads or tails

First recorded in 1675–85

Example Sentences

And flipping a coin on heads, or tails, 24 times in a row has odds of one in 16.7 million.

From BBC • Jun. 5, 2026

The iPhone Clean Up tool did OK with the grass, but couldn’t make heads or tails of the tents in the background.

From The Wall Street Journal • Nov. 30, 2025

Whether that falls heads or tails, though, generative AI isn't going to be what kills the arts and humanities.

From Salon • Aug. 29, 2023

There are only two choices: heads or tails.

From Washington Times • Feb. 10, 2023

“I can’t make heads or tails of it,” said Bronwyn.

From "Hollow City" by Ransom Riggs

Related Words

• advantage
• break
• future
• hit
• lot
• odds
• outcome
• risk