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English has many words that have multiple pronunciations for the same spelling (heteronyms) or multiple spellings for the same pronunciation (homophones). What is the longest chain of unique spelling/pronunciation pairs you can make where each pair matches either the spelling or pronunciation of the previous pair?

For example here's a length 3 chain with matching item in bold:

  1. bow/bəʊ (curved weapon which fires arrows)
  2. bow/baʊ ("I will only bow to the queen")
  3. bough/baʊ (part of a tree)

Rules:

  • No repeating pairs, even if they have different meanings (e.g. no homonyms, no coming back on pairs you've already used)
  • Use a consistent accent, dialect and phonetic notation. I've used IPA and Received Pronunciation as described by Wiktionary above, but feel free to use any reasonable set.

I've got no idea what the longest chain is!

I'm not sure what other languages this would make sense in, but it would also be interesting to see the language with the longest or shortest such chain.

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  • $\begingroup$ I don't think you just want homographs, which are words that are merely spelled the same (inviting words that have many definitions but one way of being pronounced). You want heteronyms, which are words that are spelled the same but have different pronunciations and meanings. $\endgroup$
    – Nuclear Hoagie
    Commented Jun 8, 2023 at 16:03
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    $\begingroup$ @hexomino, no requirement to alternate. $\endgroup$
    – bhh
    Commented Jun 8, 2023 at 16:18
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    $\begingroup$ Shortest chain is possibly Toki Pona, a minimalist conlang with a lexicon of only 120 words and no chains of length greater than 1 (it has no homophones at all, and theoretically no heteronyms if you strictly adhere to the official semantics of the language), though that might be cheating. My guess is that English probably has the longest as it has what is, AFAIK, the most etymologically diverse lexicon of any modern language. $\endgroup$
    – Austin Hemmelgarn
    Commented Jun 9, 2023 at 1:36
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    $\begingroup$ @AustinHemmelgarn If they don't need to alternate I think Chinese would probably beat English due to the huge amount of characters with same pronounciation $\endgroup$
    – Davis Yoshida
    Commented Jun 9, 2023 at 3:11
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    $\begingroup$ The example could be extended by prepending beau /bəʊ/. $\endgroup$
    – Toby Speight
    Commented Jun 9, 2023 at 5:48

5 Answers 5

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Let's turn it up to 11!

  1. sou /suː/: small coin
  2. sue /suː/: legal action
  3. sew /suː/: drain
  4. sew /səʊ/: stitch
  5. so /səʊ/: therefore
  6. soe /səʊ/: water vessel
  7. soh /səʊ/: musical note
  8. sow /səʊ/: plant seeds
  9. sow /saʊ/: female pig
  10. sough /saʊ/: rustling sound
  11. sough /sʌf/: ditch

There are four different pronunciations here (1-3, 4-8, 9-10 and 11).

Numbers 3, 6 and 11 are somewhat obscure, but all the words here are present in Shorter Oxford English Dictionary (fifth edition).

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    $\begingroup$ youtube.com/watch?v=Gy1ztCTrBEU $\endgroup$
    – lukas.j
    Commented Jun 9, 2023 at 11:06
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    $\begingroup$ Wow really nice, way more than I would have guessed is possible! $\endgroup$
    – bhh
    Commented Jun 9, 2023 at 14:32
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    $\begingroup$ While sowing, I saw a sow stuck in a slough, so sue the SOB for a sou that put her there? $\endgroup$
    – chux
    Commented Jun 9, 2023 at 15:23
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    $\begingroup$ I've only seen the musical note spelled sol $\endgroup$
    – nuggethead
    Commented Jun 9, 2023 at 20:44
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    $\begingroup$ @nuggethead you've never heard it described as a needle pulling thread? $\endgroup$
    – caPNCApn
    Commented Jun 12, 2023 at 3:47
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I think this is an example of length 6

tare/tɛː (noun, the weight of a container)
tear/tɛː (verb, to separate parts)
tear/tɪə (noun, drop of fluid secreted in the eye)
tier/tɪə (noun, a row, rank, or layer of articles)
tier/taɪə (noun, one who ties)
tire/taɪə (verb, to become weary)

I originally thought we had to alternate between heteronyms and homophones - this list can be extended to 7 by including

tyre/taɪə (noun, a rubber covering placed round a wheel)

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    $\begingroup$ Being a bit cheeky, we can extend this to length eight with the addition of (note capitalization) >! Tyre/**taɪə** (proper noun, an originally-Phoenician city in modern-day Lebanon) $\endgroup$
    – Lemmon
    Commented Jun 8, 2023 at 16:38
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    $\begingroup$ @Lemmon I was trying to stay away from proper nouns as that opens a whole can of worms (thinking about how people pronounce names, etc) $\endgroup$
    – hexomino
    Commented Jun 8, 2023 at 20:18
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    $\begingroup$ Seeing the non-rhotic British pronunciations here makes me wonder if there are some of these that depend on your dialect. Note that your seventh entry does fit if you use the American spelling. $\endgroup$
    – Hearth
    Commented Jun 9, 2023 at 20:30
  • $\begingroup$ @Hearth, no the American spelling wouldn't then be distinct from the 6th entry (it must differ in either spelling or pronunciation, but that would be the same in both - at least to my ear). $\endgroup$
    – Toby Speight
    Commented Jun 10, 2023 at 5:52
  • $\begingroup$ @TobySpeight I missed that they had to differ in one. $\endgroup$
    – Hearth
    Commented Jun 10, 2023 at 13:50
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I also have a length of six:

ROES (Fish Eggs)
RHOS (The Letter Rho)
ROSE (The Flower)
ROWS (Paddles A Boat)
ROWS (Quarrels)
ROUSE (To Awaken)

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  • $\begingroup$ If acronyms are allowed (unclear as I’m, writing this comment), this could be extended to length seven by swapping the first two items and doubling the new first item (it’s an acronym for an EU directive that’s significant for electronics manufacturers). $\endgroup$
    – Austin Hemmelgarn
    Commented Jun 9, 2023 at 1:47
  • $\begingroup$ There's a road near me that's spelled the same as your last word, only pronounced so that it rhymes with "house" or "mouse". (I assume it's named after some person.) It would add one more to your list if we allowed proper names. $\endgroup$
    – Darrel Hoffman
    Commented Jun 9, 2023 at 18:34
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I have 9, with two distinct pronunciations. I'm using a general American pronunciation.

doux: /du/. Sweet, describing wine
doo: /du/. Poop, as in "doo-doo"
dew: /du/. Condensation
due: /du/. Owed
do: /du/. Take action
do: /doʊ/. Musical note
dough: /doʊ/. Bread material
d'oh: /doʊ/. Interjection. Both /doʊ/ and /doʊʔ/ are common pronunciations - both can be heard in this compilation of Homer Simpson.
doe: /doʊ/. Female deer

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  • $\begingroup$ It isn't trivial: it's a pretty good start. There's a glottal stop in d'oh that doesn't work, though, and you're lacking the IPA that would meet OP's request and get you more upvotes. $\endgroup$
    – lly
    Commented Jun 11, 2023 at 16:24
  • $\begingroup$ @lly I added IPA. In my dialect, the glottal stop in d'oh is optional. Thanks! $\endgroup$
    – isaacg
    Commented Jun 13, 2023 at 2:48
  • $\begingroup$ I would've thought the glottal stop went in the middle (/dʔoʊ/), which was the problem. Perfectly normal to not notice or mark it for speakers of Murcanese, though. $\endgroup$
    – lly
    Commented Jun 13, 2023 at 5:21
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Not the longest but I came up with chain of 5 words.

right - correct
right - direction
write - the verb
rite - a religious or a solemn ceremony or act
wright - a worker skilled in the manufacture especially of wooden objects

I can extend it to 6 words but it is more-or-less pushing the boundaries

ryt/ryte - slang for "right" specially in text messages (or) a inflection of a similar Polish word

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  • $\begingroup$ I pronounce the first two identically - could you add some IPA phonetics to see how you pronounce them different to each other? $\endgroup$
    – Toby Speight
    Commented Jun 13, 2023 at 7:37

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