Homographs
Homophones
Malapropisms
Portmanteaus
Odd One Out
100

One of me is to guide or direct, the other is a heavy metal.

Lead

100

We are a group of three words. One of us is a passage in a store, another is a contraction for "I will," and the third is a small island. What are we?

aisle, I'll, and isle

100

I'm trying to have a more optical outlook on life.

Optimistic

100

Motel

motor and hotel

100

SEASON, SEASHORE, SEARCH, SEAHORSE

Search - the others contain the word "sea."

200

One of me means to plant seeds while the other means a female pig

Sow

200

We are a percussion instrument and a character that represents a concept. What are we?

cymbal and symbol

200

The dentist gave me a shot of amnesia so I wouldn't remember the pain.

Anesthesia

200

Electrocute

To injure or kill by an electric shock, blending electric and execute

200

APPLE, BANANA, GRAPE

Banana, all the others have an odd number of letters

300

One of me is the substance or meaning of something while the other is a state of peaceful happiness. 

Content

300

One is a painter's board, another is a wooden platform for shipping, and the third is the roof of your mouth. What are we?

palette, pallet, and palate

300

The villain tried to seduce the hero's identity from him.

Deduce

300

Sitcom

A type of TV show that is a situation comedy

300

SHEEP, DEER, FISH, COW

Cow - the others are both singular and plural. 

400

One of me is a substance burned for its fragrance while the other means to make someone very angry 

Incense

400

I mean careful and cautious in your actions, and my partner means separate and distinct. What are we?

discreet and discrete

400

The public library is a great suppository of knowledge.

Repository

400

Pixel

The smallest element of a display screen, from picture and element

400

LISTEN, SILENT, ELATION, ENLIST

Elation: is not an anagrams of the others.

500

One of me is an agricultural tool while the other means to cause distress to someone.

Harrow

500

I am a sarcastic or taunting remark, while my partner means to be in agreement with something. What are we?

gibe and jibe

500

All the houses on our street are contagious.

Contiguous

500

Gerrymander

A practice of manipulating electoral districts. It's a combination of the name Gerry (a Massachusetts governor) and salamander, due to a bizarre district shape.

500

KNIGHT, HONEST, DEBT, SHIP

Ship - does not contain a silent letter