I guess you are missing openssl from your sysyem, install that.
lssl is marked no, it means openssl.
Event machine has following dependencies
- OpenSSL
- libstd++
and regular ones, ruby & rake.
Try it.
And with your updated question. I doubt if bundler gem is missing.
gem install bundler
And I don't know how openssl installation in Windows work, been long i lost connection with that part of the world. ;)