re = /(?xsm) # free-spacing mode, multi-line
(?=.*?pig) # lookahead: if pig is not there, fail right away to save the effort
(?: # start counter-line-skipper (lines that don't include pig)
(?: # skip one line that doesn't have pig
^ # beginning of line
(?:(?!pig)[^\r\n])* # zero or more chars not followed by pig
(?:\r?\n) # newline chars
)
# for each line skipped, let Group 1 match an ever increasing portion of the numbers string at the bottom
(?= # lookahead
[^:]+ # skip all chars that are not colons
( # start Group 1
(?(1)\1) # if Group 1 is set, match Group 1
# (?>\1?) # alternate phrasing for the above
:\d+ # match a colon and some digits
) # end Group 1
) # end lookahead
)*+ # end counter-line-skipper: zero or more times
.*? # match
\K # drop everything we've matched so far
pig # match pig (this is the match!)
(?=[^:]+(?(1)\1):(\d+)) # capture the next number to Group 2/
str = 'my cat pi g
dog pi g
my pig
my cow
my mouse
:1:2:3:4:5:6:7'
subst = '\\2'
result = str.sub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html