I'm a teacher of English as a foreign language, and today I was reviewing some vocabulary from a book with my students. We found "irksome" and "pestering" to refer to something that is annoying. A student asked if there was a way to know when to use "irksome" and when is better to use "pestering". So, it occurred to me that maybe there is a way to know what word is the best fit to a given context, maybe a dictionary or another type of resource.

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    I think this is just Too Broad. It's important to note that "true synonyms" are exceptionally rare (either the meanings rapidly diverge, or one word is/becomes much less common than the other). For the specific case, "pestering" would almost never be used as an adjective, even though it would be likely to appear as part of a dictionary's definition of "irksome". – FumbleFingers Sep 26 '13 at 18:54
  • @FumbleFingers books.google.com/ngrams/… pestering & pestersome are used in different senses. Plus, pestersome sounds almost archaic today. – Kris Oct 18 '13 at 13:05
  • Technically, there may be many ways to choose the right word among close synonyms in a given context. However, from a pragmatic point of view, the only way to arrive at the "right" word is to be guided by usage and usage alone. Natural languages are living creatures and one needs to be alive to changes and trends. – Kris Oct 18 '13 at 13:14
  • The adjectival use of -some aids in characterizing something. The -ing suffix turns a verb into its corresponding adjective with a 'and keeps doing it' sense tagged on in some cases. – Kris Oct 18 '13 at 13:27
  • @Kris: I find only 133 instances of "pestersome" in the entire Google Books corpus, so it's a bit meaningless to talk about exactly "where/when" it might be used. But glancing at a few pages of those results, I have the impression most of them are actually recent, rather than "archaic". Just because it sounds almost credible today doesn't mean it was more credible centuries ago. The reality is it never really existed as a word, which was implicit in my original point. – FumbleFingers Oct 18 '13 at 22:03

You use irksome of something that irks you.
You use pestering of something that pesters you.

Both irk and pester refer to some irritation of their objects
(which must be human or at least capable of emotion), but they have different connotations.

Pester refers to repeated episodes of being irritated (usually by something or someone).
Irk simply means being irritated (ditto), with no reference to history or repetition.

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    Apart from the semantic distinctions, I find "Jack was a pestering child" sounds decidedly odd to me. It's the best of a bad bunch, but I think I'd rather go with "Jack was a pestersome child" – FumbleFingers Sep 26 '13 at 20:02
  • See the last verse of Tom Lehrer's version of Clementine. – John Lawler Sep 26 '13 at 20:14
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    Haha - but you'd have to admit there might be a bit of - shall we say - "artistic license" involved in a pestering sister's a festering blister. And as an "arch-Googler", I have to say it's not proved easy to establish whether Lehrer has personal knowledge whereof he speaks. Does he have any siblings? Did he really poison pigeons on the park? I think we should be told. (Certainly before accepting him as an authority on common usage! :) – FumbleFingers Sep 27 '13 at 1:37
  • Did Shakespeare know about hawks or handsaws? Did Wilde know about pestering aunts? Did Cole Porter know about beguines? Literature is not authority. – John Lawler Sep 27 '13 at 1:43
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    I'm no authority either, so I'm not trying to make a case for "objective correctness". But to me personally, pester falls into the same class as irk, bother, trouble, worry, tire, weary, burden - if someone repeatedly causes those kinds of reactions in others, I naturally lean towards saying they're [verb]some, rather than [verb]ing. It just seems more appropriate when you're trying to identify what seems more like an enduring attribute than a [potentially one-off] action. – FumbleFingers Sep 27 '13 at 14:32

There are several approaches:

A. Since the question "What word is the best fit to a given context?" is a question about collocation, you could use a collocation dictionary, such as the LTP Dictionary of Selected Collocations.

If your context or starting point is a noun such as problem, the dictionary entry will give you a list of the verbs and adjectives that collocate with it. Similarly, starting with an adjective such as opposed you are given a list of collocate adverbs (adamantly, bitterly, vehemently, implacably ...).

B: Use an online concordancer such as the COCA which allows you to do a KWIC (Keyword in context) search. This will return examples of the word in numerous authentic contexts. You can scan the results list to see if there are contexts that match yours. (You will note, for example, that pestering is much more common in a verb phrase than as an adjective.)

C: Search Google for the phrase containing the word you are interested in. So if you want to know which is the more common collocate of problem (irksome or pestering), enter each phrase, compare the number of hits and scan the results for the phrase in its context. (Irksome is about three times more common as a collocate of problem than pestering.)

D: Do a Google Books Ngram comparison. (Irksome problem is quite common, but there is no occurrence of pestering problem.)

E: Do a back translation into the mother tongue. So, for example, pestering translates as drangsalierend; plagend; piesackend in German and irksome as ärgerlich; lästig. This will often help you to see which one better fits your context.

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In Collins Thesaurus, 'Irksome' has the following synonyms:aggravating, annoying, boring, bothersome,burdensome,disagreeable,exasperating,tedious,tiresome,troublesome,trying,uninteresting,unwelcome,vexatious,vexing,wearisome.

'Pester' has the following: badger, bedevil,bother, bug, chivvy, disturb,fret, get at (inf), harass, harry, hassle,irk,nag,pick on,plague,ride,torment, worry.

So irk is a synonym of pester but not vice-versa.

Choice of words in some ways is like choosing clothes to wear. there are no hard and fast rules, you just need to find something which seems right in the context. And that can depend on how words are accepted and used in the environment you are working with.

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    'So irk is a synonym of pester but not vice-versa.' This is simply not true - synonymity (if it is considered to exist at all) is a commutative property. What you are saying here is along the lines of 'So six equals half a dozen, but half a dozen doesn't equal six.' The senses of 'irk' and 'pester' overlap partially. Collins has not listed synonyms for 'irk', which list must contain 'pester' if it is being consistent. – Edwin Ashworth Sep 26 '13 at 22:29
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    Well I'm not sure I agree. What is a synonym? A synonym does not necessarily have equal weight of meaning with its subject in quite the same way six equals half-a-dozen. Synonyms, as quoted in thesauri, are a collection of words which are 'close' in meaning - but not necessarily equal. That means that there can never be exact reciprocity. – user52780 Sep 26 '13 at 23:00

I teach upper primary school and this is a huge problem, because their experience of English language is often small and narrow and so have not used the less commonly heard synonyms, therefore they do not come with associated connotations. The only way I have found so far to help with this (because it ruins a good story to say that the china vase was bankrupt) is to subscribe to Visual Thesaurus. It gives the visual representation of the connections between words in a way that groups synonyms together, whilst providing definitions of the word as used as noun, verb, adjective (if applicable). This helps, if you can train your pupils to use it. Having just read your other responses though, I just tried COCA and it does the same thing and provides interesting teaching avenues (although at an often high level of understanding).

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