Here are some common words whose meanings are more complicated, contradictory, or surprising than most people realize.

1. Literally

This might be the most controversial word on the list.

Literally originally meant “in a literal sense,” but it is now widely used for emphasis, even when something is not literal at all.

Examples:

• The sign was literally nailed to the door.
• I literally died laughing.

Dictionaries now recognize both meanings because that is how people actually use the word.

2. Sanction

Sanction is its own opposite.

It can mean to allow or approve something, and it can also mean to punish or restrict.

Examples:

• The board sanctioned the proposal.
• The country faced economic sanctions.

Context does all the work here.

3. Oversight

This word contains two opposing ideas.

Oversight can mean careful supervision, or it can mean a mistake caused by failing to notice something.

Examples:

• The project required regulatory oversight.
• The error was an oversight.

4. Inflammable

This one looks like it should mean the opposite of what it does.

Inflammable means easily set on fire, not fireproof.

The confusion is so common that many safety labels now prefer flammable instead.

5. Dust

Dust can mean adding particles or removing them.

Examples:

• She dusted the cake with sugar.
• He dusted the shelves.

The same word describes two opposing actions.

6. Clip

Clip can mean to attach something or to remove part of it.

Examples:

• She clipped the papers together.
• He clipped the article from the newspaper.

7. Left

English loves ambiguity.

Left can describe something that remains, or something that has departed.

Examples:

• There are three cookies left.
• She left the room.

8. Cleave

Cleave is one of English’s most famous self-contradictions.

It can mean to split apart, or to stick closely together.

Both meanings survive because context keeps them separate.

9. Bolt

This word moves in opposite directions.

Examples:

• She bolted the door shut.
• The horse bolted from the field.

10. Fast

Fast can mean moving quickly, or firmly fixed in place.

Examples:

• He runs fast.
• They held fast to their plan.

11. Screen

Screen can mean to show something, or to hide it.

Examples:

• They screened the film last night.
• Tall hedges screened the house from view.

The same word covers revealing and concealing.

12. Weather

Weather can describe enduring something, or being worn down by it.

Examples:

• They weathered the storm.
• The statue has weathered over time.

It means both surviving and eroding.

13. Hold

Hold can mean to proceed with something, or to delay it.

Examples:

• Let’s hold the meeting this afternoon.
• The meeting is on hold.

14. Bound

Bound can mean restrained, or moving decisively toward a destination.

Examples:

• The book is bound in leather.
• She is bound for New York.

15. Custom

Custom can refer to a shared tradition, or something made specifically for an individual.

Examples:

• It is the local custom to remove your shoes.
• The suit was custom made for him.

Final Thought:

English is full of words that refuse to behave. Rather than being flaws, these contradictions reveal how language evolves through use, context, and habit.

Once you notice them, you start seeing how much meaning depends not on words alone, but on how we use them.

Do you love words that make you think twice? Join other word lovers by playing Wordshake Live and put your vocabulary to the test.