SSL error is due to a change in rubygems.org. You can see a solution here : https://gist.github.com/luislavena/f064211759ee0f806c88
You need to change your SSL certificate
Edit:
Manual solution to SSL issue
If you have read the above detail that describe the issue, thank you.
Now, you want to manually fix the issue with your installation.
Steps are simple:
Step 1: Obtain the new trust certificate
Step 2: Locate RubyGems certificate directory in your installation
Step 3: Copy new trust certificate
Step 4: Profit
Step 1: Obtain the new trust certificate
If you've read the previous sections, you will know what this means (and shame on you if you have not).
We need to download AddTrustExternalCARoot-2048.pem.
Use the above link and place/save this file somewhere you can later find easily (eg. your Desktop).
IMPORTANT: File must have .pem as extension. Browsers like Chrome will try to save it as plain text file. Ensure you change the filename to have .pem in it after you have downloaded it.
Step 2: Locate RubyGems certificate directory in your installation
In order for us copy this file, we need to know where to put it.
Depending on where you installed Ruby, the directory will be different.
Take for example the default installation of Ruby 2.1.5, placed in C:\Ruby21
Open a Command Prompt and type in:
C:\>gem which rubygems
C:/Ruby21/lib/ruby/2.1.0/rubygems.rb
Now, let's locate that directory. From within the same window, enter the path part up to the file extension, but using backslashes instead:
C:\>start C:\Ruby21\lib\ruby\2.1.0\rubygems
This will open a Explorer window inside the directory we indicated.
Step 3: Copy new trust certificate
Now, locate ssl_certs directory and copy the .pem file we obtained from previous step inside.
It will be listed with other files like GeoTrustGlobalCA.pem.
Step 4: Profit
There is actually no step 4. You should be able to install Ruby gems without issues now.