Installing Ruby on Rails from Source - cannot load such file -- openssl - ruby-on-rails

Question

I am on a Mac, using Lion. I am configuring my system for Ruby on Rails development but I ran into some issues. Instead of using brew or other shortcuts I want to configure Ruby on Rails from source. So, here is what I did.
Installed Ruby 2.0
Downloaded the source from the Ruby website
Compiled it by running the following code:
./configure --prefix=/Users/user/Applications/ruby2
make
make install
And made sure the $PATH file is updated to point to /Users/user/Applications/ruby2/bin
So, I am able to call ruby -v or if I do which ruby it does point to my custom compiled version of Ruby.
Installed Node.js
Downloaded the source from the main website
Compiled it by running the following code:
./configure --prefix=/Users/user/Applications/nodejs
make
make install
And made sure the $PATH file is updated to point to /Users/user/Applications/nodejs/bin
So, I am able to call node -v or if I do which node it does point to my custom compiled version of Ruby.
I also did the same steps for openssl and it is also accessible from the console or if I do which openssl it points to /Users/user/Application/openssl/bin
But still when I execute gem install rails I still get the following error:
ERROR: Loading command: install (LoadError)
cannot load such file -- openssl
ERROR: While executing gem ... (NoMethodError)
undefined method `invoke_with_build_args' for nil:NilClass
Any idea why?
System Specs
Mac Lion 10.8.4
OpenSSL 1.0.1e 11 Feb 2013
ruby 2.0.0p291
Nodejs v0.10.15

Answer 1

I managed to solve the problem by doing the following. The main problem was the step I followed to compile openssl itself.
Since I am on a 64 bit machine, I had to configure openssl by running the following command first
./configure --prefix=/Users/user/Applications/openssl darwin64-x86_64-cc
./make
./make install
And recompile ruby as such
./configure --prefix=/Users/user/Applications/ruby2 --with-openssl-dir=/Users/user/Applications/openssl
./make
./make install
Note: Even though while compiling ruby it might say... the option --with-openssl-dir is not valid or does not exist, ignore that.

Answer 2

I had very bad time with this ERROR.
Finally i done with it. There is only Once solution either you are with RVM or without RVM.
Make sure you have installed OpenSSL first BEFORE installing ruby.
First you should find where Ruby is:
whereis ruby
will list all the places where it exists on your system, then you can remove all them explicitly. Or you can use something like this:
rm -rf /usr/local/lib/ruby
rm -rf /usr/lib/ruby
rm -f /usr/local/bin/ruby
rm -f /usr/bin/ruby
rm -f /usr/local/bin/irb
rm -f /usr/bin/irb
rm -f /usr/local/bin/gem
rm -f /usr/bin/gem
THEN
sudo apt-get install zlib1g zlib1g-dev build-essential openssl libssl-dev libmysqlclient18 libmysqlclient-dev libyaml-dev curl git-core python-software-properties libpq-dev nodejs
apt-get -y update
apt-get -y install build-essential zlib1g-dev libssl-dev libreadline6-dev libyaml-dev
cd /tmp
wget http://cache.ruby-lang.org/pub/ruby/2.0/ruby-2.0.0-p247.tar.gz
tar -xvzf ruby-2.0.0-p247.tar.gz
cd ruby-2.0.0-p247/
./configure --prefix=/usr/local
make
make install
I hope this help you.