re = /(\n\n)-\s*(?!.*(?:(?<!-)\n-|\n-))/m
str = 'Here are few example strings where a leading dash character should be removed (note newlines):
- Lovely day.
- Lovely day-night cycle.
- Lovely day.
Isn\'t it?
- lovely day - isn\'t it?
- Lovely day -
isn\'t it?
Here are few example strings where leading dash character(s) should be retained (note the 2nd example, it might be tricky):
- Lovely day.
- Yeah, isn\'t it?
Lovely day.
- Yeah, isn\'t it?
- lovely day - isn\'t it?
- Yes.
- Lovely day for a -
- Walk?
'
subst = '$1'
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