re = /(?s)(?=[^:]*\d[^:]*:)(([0-9]{1,2}h)?[ ]*([0-9]{1,2}min)?:\s*)((?:.(?!(\dh\s\d{1,2}min|\dh|\d{1,2}min)))+)/
str = '1h 30min: Title
- Description Line 1
3h: SECOND TITLE
- Description Line 1
- Description Line 2
- Description Line 3
1h 14min: Title
- another Great one 42min: Title - Great Movie
- Description Line 2
- Description Line 3'
# 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