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What is the largest number of words that can be made by just adding one letter to the original word, where each iteration is a meaningful word? E.g.

HO
HON
HONE
HONES
HONEST
HONESTY

The original word can have as many letters as you want; you can add letters at the start, at the end or anywhere; and onomatopoeic words are allowed.

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  • $\begingroup$ Please also specify the starting state: do you start with a two-letter word? $\endgroup$
    – jscs
    Mar 5, 2015 at 23:27
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    $\begingroup$ "start with as many letters as you want" That doesn't make sense. You could just pick any arbitrary long word and pluralise it. Then the fun part — ensuring that substrings are also words — evaporates! $\endgroup$ Mar 6, 2015 at 12:13
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    $\begingroup$ Maybe he's looking for the largest difference between starting and ending word lengths. so adding an S to an arbitrarily long word is only worth one point. $\endgroup$
    – Kevin
    Mar 6, 2015 at 12:33
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    $\begingroup$ putting this here because it is closely related though obviously completely different questions: puzzling.stackexchange.com/questions/1911/… $\endgroup$
    – kaine
    Mar 6, 2015 at 14:00
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    $\begingroup$ I’m voting to close this question because without defining "word" it turns into an ill-defined, open-ended puzzle (and open-ended puzzles are off-topic as of May 2019) $\endgroup$
    – bobble
    Sep 9, 2021 at 5:07

7 Answers 7

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I assume you start at two letters, as in your example. I'm using the circa 2013 Words With Friends dictionary.

If you can only add to the right end of the word, 8-letter words are possible:

ba
bar
barb
barbe
barbel
barbell
barbells

ma
max
maxi
maxim
maxima
maximal
maximals

pa
pas
past
paste
paster
pastern
pasterns

re
rep
repo
repos
repose
reposer
reposers

If you can add to either end, 9-letter words are possible:

id
aid
aide
aider
aiders
raiders
braiders
abraiders

la
lap
laps
lapse
elapse
relapse
relapser
relapsers

in
pin
ping
aping
raping
craping
scraping
scrapings

at
eat
eath
heath
sheath
sheathe
sheather
sheathers

is
ais
rais
raise
raiser
raisers
praisers
upraisers

If you can add at any point, 11-letter words are possible:

pi
pig
ping
oping
coping
comping
compting
competing
completing
complecting
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10
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To add to Kevin's answer, it's possible to come up with a 11-letter word by adding letters at either end (as illustrated by the answers to this PPCG question):

ab
rab
arab
arabi
arabin
arabine
carabine
carabiner
carabinero
carabineros

ra
rah
rahm
brahm
brahma
brahman
brahmani
brahmanis
brahmanism
brahmanisms

ra
ran
fran
franc
franci
francis
francisc
francisca
franciscan
franciscans
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The longest words in the dictionary that come with my Mac are

"reversist" and "sheathery", although I can't find a definition for either of them (the earlier stages are all defined in wiktionary, though).

So

re
rev
reve
rever
revers
reversi
reversis
reversist

or

sh
she
shea
sheat
sheath
sheathe
sheather
sheathery

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    $\begingroup$ A sheathery is a shop that makes sheaths -- that is, a device for holding an edged weapon like a dagger or sword. "Reversist", I have no idea. Seems like a typo for "reservist", frankly. Neither appear to be valid Scrabble words. $\endgroup$ Mar 6, 2015 at 21:59
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The puzzle is to add one letter at a time, ANYWHERE within the word. Reasonable common words with nine letters would be: Startling (or starlings)-starling-staring-string-sting-sing-sin-in-I

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2
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a
an
can
clan
clean
cleans
cleanse
cleanser
cleansers 

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    $\begingroup$ Other answers have given longer chains, but thanks for the contribution. $\endgroup$ May 21, 2019 at 0:26
1
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Starling could be an option.

In 
Sin 
Sing 
Sting 
String
Staring
Starling
Startling 

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2
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    $\begingroup$ Then startling, for nine letters. $\endgroup$ Dec 23, 2018 at 16:13
  • $\begingroup$ or I IN SIN SING SINGE SINGER SINGERS STINGERS STRINGERS $\endgroup$
    – DJA
    Nov 11, 2019 at 0:02
0
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Adding at the end, I give you contrasters (11 letters). For 10 letters, I found these:

contraster
Romanisers
contrasted 
pastoraled 
pastorales 
minimisers 
quartettes 
quintettes 

I used Aspell SCOWL dictionary.

Using a bigger, lower quality, list, I can find territorialised and territorialists (15), but there are many false positives in that list.

Of course, one can cheat. If you start with: dichlorodiphenyltrichloroethane you can just add an s and put yourself in the nice sum of 32 letters. If we remove chemicals (they can, after all, be arbitrarily long), you have the classic antidisestablishmentarianism, that, in its plural form, is 29 letters long.

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  • $\begingroup$ I'm confused. What are the letters being added? $\endgroup$
    – xnor
    Mar 6, 2015 at 22:39
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    $\begingroup$ @xnor always at the end. $\endgroup$
    – Davidmh
    Mar 6, 2015 at 22:40
  • $\begingroup$ Oh, I see, the OP said "start with as many letters as you want", so you're just making a single addition. $\endgroup$
    – xnor
    Mar 6, 2015 at 22:41
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    $\begingroup$ How can there be plural antidisestablishmentarianisms? $\endgroup$ Mar 7, 2015 at 4:10

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