#!/bin/bash

begin="" # The unshortened beginning of the path.
shortbegin="" # The shortened beginning of the path.
current="" # The section of the path we're currently working on.
end="${2:-$(pwd)}/" # The unmodified rest of the path.

if [[ "$end" =~ "$HOME" ]]; then
    INHOME=1
    end="${end#$HOME}" #strip /home/username from start of string
    begin="$HOME"      #start expansion from the right spot
else
    INHOME=0
fi

end="${end#/}" # Strip the first /
shortenedpath="$end" # The whole path, to check the length.
maxlength="${1:-0}"

shopt -q nullglob && NGV="-s" || NGV="-u" # Store the value for later.
shopt -s nullglob    # Without this, anything that doesn't exist in the filesystem turns into */*/*/...

while [[ "$end" ]] && (( ${#shortenedpath} > maxlength ))
do
  current="${end%%/*}" # everything before the first /
  end="${end#*/}"    # everything after the first /

  shortcur="$current"
  shortcurstar="$current" # No star if we don't shorten it.

  for ((i=${#current}-2; i>=0; i--)); do
    subcurrent="${current:0:i}"
    matching=("$begin/$subcurrent"*) # Array of all files that start with $subcurrent. 
    (( ${#matching[*]} != 1 )) && break # Stop shortening if more than one file matches.
    shortcur="$subcurrent"
    shortcurstar="$subcurrent*"
  done

  #advance
  begin="$begin/$current"
  shortbegin="$shortbegin/$shortcurstar"
  shortenedpath="$shortbegin/$end"
done

shortenedpath="${shortenedpath%/}" # strip trailing /
shortenedpath="${shortenedpath#/}" # strip leading /

if [ $INHOME -eq 1 ]; then
  echo "~/$shortenedpath" #make sure it starts with ~/
else
  echo "/$shortenedpath" # Make sure it starts with /
fi

shopt "$NGV" nullglob # Reset nullglob in case this is being used as a function.