re = /^•.*\K\r?\n\r?\n(?=(?!•).*\r?\n\r?\n•)/m
str = '• This is a bulleted line.
This should remain on a separate line
because this line is not bulleted
• This is a bulleted line.
This line SHOULD be absorbed into the one above
• because this line which follows it is bulleted too.'
subst = ' '
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