re = /\bjack.*?jill\b/m
str = 'jackjill
jack jill
jack-jill
jack&jill
jack & jill
jack-&-jill
jack and jill
jackandjill
jack-and-jill
jack n jill
jackandjill
jackandjilld
jacskandjill
'
subst = 'Jack & Jill'
result = str.gsub(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