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This is based on a word game that as far as I know was invented by my friend's Dad.

The goal is to make as long a word as you can, starting from any three-letter word, using the following rule: You must always change one of the letters in the word, and you must always add a new letter to the word, and the result must always be a word.

So for example, you could start from cat to get

cat
fate             [change the c to an f, add an e]
grate            [change the f to an r, add a g]
graced           [change the t to a c, add a d]
cracked          [change the g to a c, add a k]
crackers         [change the d to an r, add an s]

For 8 letters. Note that you can change any letter, and the letter you add can be at the beginning, the end or somewhere else. However, you have the following restrictions:

  • you always have to add one letter and change one letter

  • you can't add a letter and then change it in the same move

To be absolutely clear on that last rule: a move isn't allowed if it is possible to get from the longer word to the shorter one just by removing one letter. (Thanks to astralfenix for suggesting this clarification.)

Typical scrabble rules apply, e.g. no proper nouns.

In case of disputes regarding words of length 8 or less we'll use this word list, which I think is the one used for scrabble. For words longer than 8 characters, any reasonable dictionary will do. Whoever gets the longest word first will win. I don't know the longest possible word.

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  • $\begingroup$ I hope the tag is OK. This doesn't fit the tag description for "wordplay" or "word-puzzle", and there didn't seem to be one for puzzles based on words themselves. $\endgroup$
    – Nathaniel
    Mar 3 '16 at 7:11
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    $\begingroup$ There is a problem with your chosen word list. Being a Scrabble word list, this one contains words only upto 8 letters length. If the word has to be on that list, then you have yourself limited the scope to 8 letter words. $\endgroup$
    – CodeNewbie
    Mar 3 '16 at 8:39
  • $\begingroup$ @CodeNewbie eep, I hadn't thought of that. Sugestions for an alternate wordlist are welcome! $\endgroup$
    – Nathaniel
    Mar 3 '16 at 8:56
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    $\begingroup$ The "clarification" seems to me to be a change of specification. It is possible to get from his to this by changing one letter and then making an insertion: his -> tis -> this; so this would seem to be valid by the original rules but prohibited by the "clarification". (On the other hand, his to hiss is impossible under both). $\endgroup$
    – Peter Taylor
    Mar 3 '16 at 14:36
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    $\begingroup$ I’m voting to close this question because open-ended puzzles are off-topic $\endgroup$
    – bobble
    May 9 at 18:50
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A sequence reaching 15 letters:

fun
lung
suing
cluing
cloying
cooeying
conveying
conventing
conventions
conventional
conventionary
conventionally
conventionality
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There are a few 15-letter words which can be reached. This sequence mainly avoids obscure words:

UTE
BATE
CRATE
BERATE
ACERATE
ACCURATE
ACICULATE
PANICULATE
PARTICULATE
INARTICULATE
DISARTICULATE
DISARTICULATOR
DISARTICULATION

I had a hunch that -TION would be a good way to get long words, and that gives this sequence:

BON
CION
ANION
ACTION
DICTION
EVICTION
EMICATION
DEDICATION
DEIFICATION
AERIFICATION
METRIFICATION
GENTRIFICATION
DENITRIFICATION

(Cion is an obscure spelling of scion).

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flu
plus      [change the f to a p, add an s]
blush     [change the p to a b, add an h]
slushy    [change the b to an s, add a y]
plushly   [change the s to a p, add an l]
slushily  [change the p to an s, add an i]
squashily [change the l to a q, add an a]

reference to legitimate the word (adv): squashily

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Here is a sequence that reaches 10 letters. 

lap         
lace        p->c +e
laser       c->s +r
basher      l->b +h
bushier     a->u +i
slushier    b->l +s
slushiest   r->s +t
squashiest  l->q +a

All words are valid on Dictionary.com.

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    $\begingroup$ errm. how did you change face to laser? there are 2 replacements if I am not wrong? f->l & c->s $\endgroup$
    – canova
    Mar 3 '16 at 11:28
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    $\begingroup$ laser is reachable from lace, which is reachable from lee. $\endgroup$
    – Peter Taylor
    Mar 3 '16 at 12:34
  • $\begingroup$ @SirSC: Thanks again for catching that error. :) $\endgroup$
    – CodeNewbie
    Mar 3 '16 at 13:08
  • $\begingroup$ you're welcome mate. btw rule is changed according to the op so you can improve your answer i guess ^^ $\endgroup$
    – canova
    Mar 3 '16 at 13:13
  • $\begingroup$ @SirSC: I hate these open-ended questions where the constraints keep changing. -.- $\endgroup$
    – CodeNewbie
    Mar 3 '16 at 13:26
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Another sequence. You could go farther with hyphenated words. I believe the jury is out on whether re-spraining is hyphenated or not.

man          +b, m->r  
bran         +r, m->b  
bring        +g, a->i  
airing       +a, b->i  
railing      +r, r->l  
draining     +d, l->n  
detaining    +e, r->t  
retraining   +r, d->r
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same 8 words attempts: 

act             
race             +r, t -> e  
raven            +n, c -> v  
raving           +g, e -> i  
ranging          +g, v -> n  
reneging         +e, a -> e  
rendering        +d, g -> r  
meandering       +a, r -> m
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gat    
batt    
bates    
barter    
battery    
battered    
battersea
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    $\begingroup$ I'm with you until the last word. Battersea is a place name and is not on the supplied list. Good work, though. $\endgroup$
    – Hugh Meyers
    Mar 3 '16 at 8:18
  • $\begingroup$ wanted to remind that: "the letter you change can't be the one you just added". you do this several times $\endgroup$
    – canova
    Mar 3 '16 at 9:54
  • $\begingroup$ @SirSC as far as I can see he doesn't do that. $\endgroup$
    – Nathaniel
    Mar 3 '16 at 11:23
  • $\begingroup$ batt to bates - he added "s" , bates to barter. he changed "s". barter to battery - he added "y" , battery to battered - he changed "y". did 2 times. $\endgroup$
    – canova
    Mar 3 '16 at 11:25
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    $\begingroup$ @SirSC oh, I see what you mean. This is OK. I meant you can't add a letter and then change that letter in the same move. Changing the one from the previous move is OK. I'll edit the question to try and make it clearer. $\endgroup$
    – Nathaniel
    Mar 3 '16 at 12:21

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