re = /(?sm)(?=^((?:Item 1|Item 1a|Item 1b).*?^(?:Item 2|Item 2a|Item 2b)))/
str = 'Item 1 ....
Item 2 ....
Item 1 ....
....
....
Item 2 ....
Item 1 ....
Item 2
Item 1a ....
....
....
....
....
Item 2b ....'
# Print the match result
str.scan(re) do |match|
puts match.to_s
end
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