Homophones: Sound-Alike Words

Homophones are words that sound alike but don’t necessarily have similar meanings; they could have totally different definitions.

However, there are some that not only sound alike but also have similar meanings. That’s what I want to tackle here.

Sound-alike words with similar meanings

Do you ever wonder whether to use one word over another when they both seem to mean the same or similar things? I know I do. This is when the dictionary comes out.

I’ve chosen three examples that I’ve had trouble with in the past. I thought (before I started writing this post) that I had a fairly clear, albeit slightly clouded, grip on the differences in meaning.

Do I inquire about how to farther my grammar skills to insure understanding? Or do I enquire about how to further my grammar skills to ensure understanding?

Out came my trusty and huge Oxford Dictionary of English. It took a bit of investigating and I had to read the ‘Usage’ section for each example.

This is what I found out.

Further vs Farther

Both are adverbs and adjectives. Farther is a variant form of further and the two are generally interchangeable and equally correct.

While the two words can be used in the sense, ‘at, to, or by a greater distance’, it would be unusual to use farther in an abstract or metaphorical sense.

Walking farther down the road than my friend and walking further down the road than my friend are both correct.

Going farther in one’s career is not incorrect, but would be unusual. Going further in one’s career is correct because we are not talking measurable distance – besides, it reads better.

Having looked in the Oxford Dictionary and found a comprehensive explanation, I then found a succinct explanation in Strunk and White: ‘The Elements of Style’:

“The two words are commonly interchanged, but there is a distinction worth observing: farther serves best as a distance word, further as a time or quantity word. You chase a ball farther than the other fellow, you pursue a subject further.”

Good old Strunk and White’s. Not a superfluous word in sight.

Inquire vs Enquire

These are also interchangeable words. Both are verbs.

Enquire means to ask for information, or to investigate or look into something. Inquire has the same meaning, but is chiefly used in US English. In British English it seems to have been commonly replaced by enquire.

The exception in British English is that the word inquiry is commonly used to describe an official investigation into something, but the word enquiry is also correct in this sense.

This can seem confusing, but when in doubt use what the dictionary recommends as the common usage. If there is any further doubt, consult Strunk and White’s, or your favoured style bible, it may be mentioned in there.

Insure vs Ensure

I thought I had it sewn up with these two words. Insure, I told myself authoritatively, means to pay someone money in order to get compensation if something goes wrong and ensure means to make certain that something happens.

I was surprised to find that insure or ensure are both correct and interchangeable. The exception is in the commercial sense of handing over money in return for compensation for loss or damage to property or person. In this sense insure is the correct word and ensure is not.

Generally speaking, you can insure or ensure against something happening, as in appeasing someone to ensure/insure something does not happen.

Again, in British English, ensure is generally the most commonly used.


When in doubt, it is worth hauling out your favourite dictionary and checking. In the three examples given here, you won’t generally go wrong if you use one in favour of another, but there are the stumbling blocks; we take out insurance on our cars and homes, not ensurance.

To further your understanding of grammar and language, take out your reference books and consult them. An enquiring mind will ensure against embarrassing mistakes.

What similarly spelt words confuse you? What are your stumbling blocks?