Yeah, I was afraid you wanted that and actually started writting a lot about it, but that would have been confusing so I just hoped...
To do that, you need to be able to do a wildcard match based on the line in the file, and $read doesn't allow you to do that.
We can loop on all lines in the file ourselves but it could be slow depending on the number of lines.., they are better way to accomplish this.
A very nice way to do that is to use hash tables, $hfind is a powerful tool which can do what you want.
Just like in the text file, you'll use the hash table as an unordered list of string like "the", but this time you add ** around it: *the*.
After that you use $hfind(table,<word from sentence>,1,W).item which will return *the* if <word from sentence> is "their" for example.

Code:
on *:start:{
  hmake matchinglist
  if ($exists(matchinglist)) hload matchinglist matchinglist 
}
alias addtolist {
  hadd matchinglist * $+ $1* 
  hsave matchinglist matchinglist
}
alias delfromlist {
  if ($hget(matchinglist,* $+ $1*) != $null) { 
    hdel matchinglist * $+ $1*
    hsave matchinglist matchinglist 
 }
}
Put that in your remote and use "/addtolist the" and "/delfromlist the" to add/remove stuff, then:

Code:
on *:text:*:#chan:{
  var %a 1,%v
  while ($gettok($1-,%a,32) != $null) {
    %v = $v1
    if ($hfind(matchinglist,%v,1,W).item != $null) {
      echo $chan The word %v matches the entry $v1
    }
    inc %a
  }
}


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