50 Problem Words and Phrases

By Mark Nichol

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Oh, what a tangled web we weave when first we practice to conceive written communication. So many pairs or trios of words and phrases stymie us with their resemblance to each other. Here’s a quick guide to alleviate (or is it ameliorate?) your suffering:

1. a while / awhile: “A while” is a noun phrase; awhile is an adverb.

2. all together / altogether: All together now — “We will refrain from using that two-word phrase to end sentences like this one altogether.”

3. amend / emend: To amend is to change; to emend is to correct.

4. amount / number: Amount refers to a mass (“The amount saved is considerable”); number refers to a quantity (“The number of dollars saved is considerable”).

5. between / among: The distinction is not whether you refer to two people or things or to three or more; it’s whether you refer to one thing and another or to a collective or undefined number — “Walk among the trees,” but “Walk between two trees.”

6. biannual / biennial: Biannual means twice a year; biennial means once every two years.

7. bring / take: If it’s coming toward you, it’s being brought. If it’s headed away from you, it’s being taken.

8. compare to / compare with: “Comparing to” implies similarity alone; “compare with” implies contrast as well.

9. compliment / complement: To compliment is to praise; to complement is to complete.

10. comprise, consist of / compose, constitute: Comprise means “include,” so test by replacement — “is included of” is nonsense, and so is “is comprised of.” The whole comprises the parts or consists of the parts, but the parts compose or constitute the whole.

11. connote / denote: To connote is to convey (“Air quotes connote skepticism or irony”); to denote is to specify (“A stop sign denotes the requirement to halt”).

12. continual / continuous: Continual events are frequently repeated, or intermittent. Continuous events are uninterrupted, or constant.

13. credible / credulous: To be credible is to be authoritative; to be credulous is to be gullible.

14. deserts / desserts: If you eat only cake, pie, ice cream, and the like, you eat just desserts. If you have it coming to you, you get your just deserts as well. (However, the connotation is negative, so hit the gym.)

15. different from / different than: The former phrase is preferred in formal writing; but “differently than” is always correct usage.

16. discreet / discrete: Discreet means “subtle”; discrete means “separate.” (“He discreetly reminded them of their discrete meanings.”)

17. each other / one another: “One another” is preferred in formal writing when more than two of something are being discussed.

18. economic / economical: Economic refers to the science of economics; economical suggests frugality.

19. elemental/elementary: What’s elemental is essential or integral to nature; what’s elementary is basic.

20. ensure / insure / assure: To ensure is to guarantee, to insure is to indemnify, and to assure is to comfort or convince.

21. epidemic / endemic / pandemic: An epidemic is the outbreak of disease in a limited place and time; an endemic disease is a recurring one peculiar to a place or population; a pandemic is pervasive over a wide geographical area.

22. forgo / forego: To forgo is to go without; to forego is to go before (and is generally used only in the forms foregoing and foregone, which are themselves rare).

23. gibe / jibe / jive: To gibe (soft g, as in gym) is to taunt or insult (though jibe is an alternate spelling), to jibe with is to coincide or fit, to jive is to deceive.

24. historic / historical: Something historic is remarkable for its impact on history; something historical is simply an event in history.

25. home in / hone in: To home in is to close in; to hone in is to confuse one word for another. (“Hone in” has no meaning.)

26. jealousy / envy: Jealousy is resentment; envy is covetousness.

27. lay / lie: Lay is transitive, associated with a direct object — “Lay that pencil down.” “Yesterday, I laid that pencil down.” “That pencil has been laid down.” Lie is intransitive, not so associated — “Lie down.” “Last night, I lay down.” “It was my plan to have lain down already.

28. leach / leech: To leach is to dissolve by percolation; to leech is to remove blood with a leech or to exhaust; as a noun, it means a parasitic worm or the human figurative equivalent, or the edge of a sail (also spelled leach).

29. libel / slander: Libel is written defamation; slander is the spoken equivalent.

30. may / might: May refers to factual or possible; might is appropriate for the hypothetical or counterfactual.

31. nauseous / nauseated: To be nauseous is to cause sickness. To be nauseated is to feel sick.

32. notable / noticeable / noteworthy: Something notable is worthy of note. Something noticeable is capable of being noticed. Noteworthy is a synonym of notable, though the former implies the unusual and the latter the commendable.

33. partly / partially: Partly means “in part”; partially means “incomplete” or, rarely, is an antonym for unfairly.

34. peak / pique: To peak is to reach the pinnacle; to pique is to arouse interest or to bother.

35. people / persons: People has assumed primacy; persons is reserved mostly as a synonym for bodies (“those belongings carried on their persons”).

36. persuade / convince: To persuade someone is to motivate them to do something; to convince someone is to lead them to understand or believe.

37. predominantly / predominately: Both forms are correct, but predominantly predominates.

38. purposely / purposefully: What’s done purposely is done on purpose; what’s done purposefully is done with a purpose.

39. regrettably / regretfully: Regrettably is a synonym for unfortunately; regretfully means just that — full of regret.

40. repetitive / repetitious: Both terms have acquired a negative connotation, but the former retains a more neutral meaning.

41. sensual / sensuous: Sensual has an erotic connotation; sensuous refers more neutrally to what is pleasurable to the senses.

42. since / because: Informally, these terms are interchangeable, but in formal writing, since should be used only to refer to time.

43. stationary / stationery: To be stationary is to stand still; stationery refers to letter-writing materials.

44. that / which: That is used restrictively (“The pencil that is sharp” — among more than one pencil, the one with that characteristic); which is employed nonrestrictively (“The pencil, which is sharp” — one pencil alone, possessing that characteristic). The distinction is rarely observed other than in American English.

45. tortuous / torturous: A tortuous experience is a winding one; a torturous one is painful.

46. transcript / transcription: A transcript is a thing; a transcription is the process of creating it.

47. verbal / oral: Verbal refers to both written and spoken communication, but oral is useful for distinguishing the latter from the former.

48. while / although / whereas: Informally, while is a synonym for the other two terms, but in formal writing it should be reserved for temporal connotations.

49. wreak / wreck: These terms do not share etymological origin; you wreck a party, but you do so by wreaking havoc.

50. whether / if: Both words are correct in expressing a choice, but the former is more appropriate in formal writing (“I can’t decide whether to go”), whereas the latter is better reserved for reference to possibility or probability (“I’ll go if you do”).

Keep learning! Browse the Misused Words category, check our popular posts, or choose a related post below:

103 Responses to “50 Problem Words and Phrases”

  • Tony Hearn

    Excellently useful listing, Mark.

    “15. different from / different than: The former phrase is preferred in formal writing; but “differently than” is always correct usage.” Yes, but in US usage. In British English and its relatives “differently” cannot be followed by “than”. We use “to” and “from”, with “from” as the preferred use. Maeve has a 2007 posting on this. She notes that Fowler in his English Usage does not mention “different than”. Presumably because it didn’t register on his radar. It is still generally regarded here as unacceptable.

    “44. […] The distinction is rarely observed other than in American English.” More’s the pity! I’m with you on this one, though I wonder if the battle isn’t on the way to being lost.

  • Niko

    Great article!

    My English teacher never told me this.

    Thank You!

  • Fisayo @ Secrets of Entrepreneurship

    Great article. I’ve saved it. Thanks for sharing

  • Rebecca

    Thanks for this great list!

    1. a while / awhile: “A while” is a noun phrase; awhile is an adverb. This one usually ‘wreaks’ havoc on one’s writing.

  • Roberta B.

    Excellent list! #23 to jibe – has nautical origins (tack and jibe) where to jibe is to go with the wind. So, when two things jibe or jibe with each other, it means they go together.

  • Precise Edit

    One that I often have to fix is “alright” vs. “all right.” “Alright” is substandard. The correct term is “all right.”

    #42 (“since” vs. “because”) is great. We use “because” to establish causality and “since” for a passage of time. If we use “since” for causality (which is possible), the reader may have to stop and figure out what you mean. This is more work than we want the reader to do, and it detracts from engagement in the ideas being expressed.

    Another one we often correct is “less” vs. “fewer.” Here’s what “Which Word Do I Use?” has to say about these 2 problem words.

    “Less” vs. “Fewer”

    This one is pretty simple, and most people would recognize any error if they stopped long enough to think about it. The problem is that we are more accustomed to saying “less” than we are to saying “fewer,” so we tend to use “less” for everything, even when it’s the wrong word. I’ll show you the difference so that you can use these words consciously and correctly.

    “Less” refers to quantities that we cannot count, to things that are a single whole, or to a concept.

    For example, freedom is a concept, so it is a single thing. You can’t have 2 freedoms. (You can have multiple privileges or rights that we call freedoms, but that is something different. Here, we’re referring to the general concept of freedom, which is singular.)

    Fat is a single thing, a term we use to refer to all the extra weight our bodies carry around. You can have two fat cells, but you only have one fat.

    Finally, sand is a single thing, a single quantity comprised of grains of sand.

    Here’s how these examples are used in sentences.
    “People of the Middle Ages had less freedom than people have today.”
    “After finishing my diet, I had less fat around my hips.”
    “The beach had less sand after the storm.”

    “Fewer” refers to quantities that we can count, things that we can have in quantities.

    For example, you can have multiple light bulbs in your home, and you can count them. Although coffee as a type of drink is singular (requiring “less”), we can also refer to individual servings or portions as coffees; the portions can be counted. Finally, a birthday is an event, and you can count the number of birthdays.

    Here’s how these examples are used in sentences.

    “If we remember to turn off the lights when we leave, we will need to buy fewer light bulbs.”
    “I bought fewer coffees this week than last week.”
    “My mother wishes that she had had fewer birthdays.”

    One good trick to determine whether you have a countable or non-countable thing is to use the word in a sentence and replace it with a pronoun. If you replace the word with the singular pronoun “it,” then you have a non-countable thing and will use “less.” If you replace the word with the plural pronoun “they” or “them,” then you have a countable thing and will use “fewer.”

    Let’s try this trick and see how it works.

    “The pickles were sour.” Are “pickles” countable or not? We can replace “pickles” with the pronoun “they,” as follows: “They were sour.” From this we know that “pickles” is a multiple, countable thing, so we can use “fewer.”

    “I seem to have fewer pickles than I expected.”

    Here’s another way to think about this: If you can have a few of them, use “fewer.”

    Remember: If you can count individual items, use “fewer.” If you can’t, then use “less.”

  • Deborah H

    A little trick for teaching youngsters about lay and lie:
    1. To LAY something down is to PLACE it. The long A sound is the key.
    2. To LIE is to RECLINE. The long I sound ties the two ideas together.

    Re: wreak. I had a newspaper editor who told me that if I ever wrote “wreak” in a story, he would wreck my knuckles. I like my knuckles so I never, ever used the word “wreak.”

  • Craig

    Good list, but I feel you missed further and farther.

  • S

    First of all, I’m a new visitor to this website and have been dropping in quite regularly since discovering it. It’s an excellent resource and I enjoy reading through the lively discussion too. So, many thanks to its authors!

    I had a quick question/suggestion regarding no. 11 here – I wondered whether ‘connoting’ was more like ‘implying’ or ‘suggesting’, rather than simply ‘conveying’?

  • William Wilgus

    Try again, this is wrong:
    “24. historic / historical: Something historic is remarkable for its impact on history; something historical is simply an event in history.”

    This is correct:
    Historic: an event, place, or ‘thing’ in history. Historical: something regarding or dealing with an event, place, or thing in history. Examples: Gettysburg is a historic battlefield; a Gettysburg Historical Society would be a society about the history of Gettysburg.

  • Brian Laney

    These tips are really informative.

    Check out the book “Inside a Dog” if you’re interested in humorous, yet helpful grammar advice on commonly made mistakes:

  • Mark Nichol


    Yes, connote means “imply” as as well as “convey.” I was trying to keep my annotation brief, but you’re right.

  • Sharon Roffey

    To follow on from Deborah H’s “little trick for teaching youngsters”. I have always been able to smooth furrowed brows (and not just those of youngsters!) by using “e for envelope” to explain the difference between stationary / stationery (#43 in the list above).

    If you do another similar list, then bought / brought also seems to perplex otherwise intelligent beings. 🙂

    I agree with all the other responses concerning the usefulness of this list. Good stuff.

  • Philip Rees

    Partially is a synonym for unfairly, not an antonym.

  • Precise Edit

    Craig: Regarding “farther” and “further”
    Here’s what “Which Word Do I Use?” has to say about those words:

    These two words are very similar in meaning, and that is why they cause so much confusion. They both refer to extending or going beyond a certain point. Many writers use only one word for all meanings, but this mistake reveals the writer’s misunderstanding of both the word meanings and the concepts behind these two words.

    “Farther” refers specifically to a greater measurable distance. You can drive farther, see farther, throw a ball farther. Then you can go measure how much farther you drove, saw, etc. The error, obviously, is to use “further,” which does not indicate a measurable distance.

    “Further” refers specifically to extending a concept, spending more time, or, basically, any type of extension or expansion that is not a measurable distance. This is the trickier word, so I’ll give you a few correct examples.

    “Let’s talk about your problems further.”
    “He made further progress on his dissertation.”
    “The boy made further noise after being scolded by the librarian.”

    Remember: “Farther” for [measurable] distance; “further” for everything else.

  • ozgott

    I was hoping to see “affect – effect”. Oh well, I guess I’ll never get it right.

  • Vanessa

    Two other examples I’ve noticed people always seem to get mixed up on:

    Practise / Practice and affect / effect

    I always remember practise being the verb and practice the noun. But when someone asks me how to tell the difference between ‘affect’ and ‘effect’, I don’t know how to explain it. I know which one to use, but I don’t know why…

  • Don E. Chute

    I am glad I stumbled upon you. I may even subscribe by mail for up to date information and the Ebook.

    Thank You!

  • Sharon Roffey

    Conform to / conform with is also a killer … and it seems as though the jury is still out. I generally choose the “with” to match the Latin “con”. However, there are times when conform to is, apparently, the correct format. I now get around it by using “comply with”. It’s a one-size-fits all solution and so much easier. If an explanation on conform is forthcoming in future “DailyWritingTips” that would be just great.

    Then there’s replace with / replace by …

    BTW, Don: the daily e-mail is well worth it. So is the e-book.

  • Peter

    I always remember practise being the verb and practice the noun.

    And similarly for license/license, etc. (Doesn’t apply in American English, though; they only have practice/licence/etc.)

  • conor hogan

    Repeat after me “There are colloquialisms” also repeat after me “English is not French, there is no language academy that codifies the language”.

  • fajas colombianas

    I get mixed up with a while and awhile alot.

  • Alan Hutcheson

    Stumbleupon finally sends me to something I can use. Great article. Duly printed and I am sure will be referred to regularly.

  • œ

    What a great idea for an article! English being my second language, I have found myself struggle with a few of the listed pairs in the past, and I’ll be sure to come back to this list in my uncertainty.

    However, one duo that I’ve seen mis-used countless times even by native English-speakers seems to be missing:

    “then” vs. “than”

    True, these are both little words, almost too small to notice. But maybe that is precisely the reason so many people think one thing is “better then” another and they “went shopping and than for a coffee”.
    Or maybe I am simply super sensitive to this mistake and therefore see it more often than it is generally made?

    “farther” and “further” always do cause me trouble, and your explanation has helped clear it up to a degree. I am still confused though: “The hotel is a little further down the road” sounds natural enough, much more common than “[…] farther down the road”, but following your guide “farther” would be correct?

  • Roberta B.

    affect v. effect – A very simple rule of thumb is that affect is a verb (to influence) and effect is a noun (a result of some sort). To “effect” as a verb means to cause, and generally it only shows up in technical writing – e.g., to effect a change or to effect a result. So, the simple rule is the safest and easiest to remember.

  • Mauri Moore

    What about ability/capabililty?

  • John C

    “Amount” and “Number” run afoul of the near ubiquitous supermarket gaff of “Fewer” and “Less”. It a matter of countability or not.

  • Dave Cleinman

    I thought these were pretty much common knowledge these days, until I started my article directory! After rejecting over a hundred articles during the past five days, I realize how many people need this information.

    Hope you don’t mind if I link to it!


    Dave Cleinman

  • John C

    “Walk between the trees” i.e. without bumping into them with a sense of direction and “walk among the trees” i.e to give the mood of enjoying the walk and the trees. Both work for me; it’s a question of what you want to say.

  • John Morris

    Usage of “in” and “at”

    e.g. He lived in Canberra or “He lived at Canberra”

  • Sander Blome

    Do I write too much and trouble with the language too little? A mentor and an editor are keys. What I need most is an agent. Are there any honest agents out there?

  • sora


  • Sue Hutchings

    The two terms which I find annoying when transposed, (and which I have noticed in two of the last five books I have read) are ‘upwind’ and ‘downwind’. The characters were relieved that they were upwind of the creature chasing them. Ask any hunter: you want to be downwind so it/they can’t smell you and snack on you.

  • dan

    Over/more than: over is a preposition (jump over the fence)not over 50 miles….More than 50 miles, more than 100 dollars…not over 100 dollars.

  • Stella

    Continual and continuous are synonymous and therefore interchangeable when the mean incessant.
    “That” introduces a defining, exclusive clause, “which” is non-defining additional information. Well-educated people usually differentiate them.
    “Partially” is a synonym, not an antonym of “unfairly”.
    “Whether” isn’t all that formal, nor is it always interchangeable with “if”.
    Does “I can’t decide if to go” sound right?

  • Ganesha24

    Love it. Thanks for this.

  • GEH

    To effect change, you must have an effect on circumstances. But no silly affectations, please. They don’t affect me.

  • Delia

    Here is a link to a previous column on this site that says “differently than” is NOT “always correct usage,” as you hold in #15.

  • Precise Edit

    oe: Yes, the hotel is a little FARTHER down the road. The distance to the hotel is measurable, not conceptual.

    Here’s another example of “farther” and “further”: “If we travel farther, we will have the opportunity to speak further. Furthermore, this is a beautiful day to drive farther.”

    “Farther” is akin to “longer.”
    “Further” is akin to “additional.”

    However, you raise an interesting point: what sounds right vs. what is right. Most people speak and write according to what they hear and read. We say “Well, that sounds/looks right to me.”

    I think this is one reason why that pesky apostrophe-S for plurals is becoming so common: many people are accustomed to seeing it, so it looks right (or doesn’t catch their attention at all). Another common examples of this is the use of “me and him” as the subject of a sentence (or other variations), as in “Me and him are going to the movies on Saturday.”

  • John C

    7 bring/take : The distinction given is correct but trivial and, by and large, everybody get it right when “you” are not doing the taking or bringing. But what happens when you are reporting on your bringing or taking something somewhere? This is more subtle and requires that there be a reference location; implicit or explicit. E.G. In conversation about a party Jake would say “I brought the beer”. But the next morning, at home explaining some missing inventory, it would be “I took the beer to the party”.

  • Gene


    The first of these is a verb; the second one is a noun.

  • Brynn

    Great article. Thank you. I’m here via Stumbleupon. I’ll definitely be back.

  • Gene

    Possessive nouns/plural nouns:

    Only use apostrophes to show possession, or missing letters in a contraction.

    Possessive nouns: Always put the apostrophe after who/what the ‘something’ belongs to. For example: the (single) child’s toys, the (multiple) children’s toys, the (one) boy’s toys, the (two) boys’ toys

    Contractions: can + not = can’t. The apostrophe stands for the missing n and o.

    Plural nouns only need an apostrophe if they are possessive; if no possession is being indicated, don’t use an apostrophe. Examples: I have two dogs. You can eat three pieces of pizza.

  • phil

    deserts/desserts: A single s ususally refers to a desert, such as the Gobi Desert. A barren area of a land with little rainfall. Only in the pharse “just deserts” does it mean you get what you “deser”ved.

  • greg

    like i said ,who taught you how spoke.lol.

  • Mary K. Smalley

    Love this site. Thanks.

  • Delia

    Here is a URL for an earlier column on this site about different from/to/than (#15)

    It seems not everyone thinks “differently than” is “always correct usage.”

  • Dave

    Over/More than.

    Over implies relationship in space: The painting hangs over the mantle.

    More than implies quantity: Last year he earned more than $100,000 with his websites.

  • margaret francis

    The confusion that exists between “affect” and “effect” deserves a post of its own.

  • lawg

    Wow, this was terrific, thank you! Even the comments are helpful! I’m particularly annoyed by the misuse of ensure and insure so I’m glad you included that one.

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