Xbee Communication with my PC

Hello once again everyone.

I am still having trouble getting my laptop to talk to my arduino via serial through the xbees, and I think I have boiled down the problem to one of two areas of concern.

The first is that I have no actual program sending the serial to the arduino. I'm not sure if using PuTTy/X-CTU's terminal feature is enough to send serial to my arduino or if I need to write/implement a C++ program similar to this one: Arduino Playground - CPPWindows

The second area for concern is that my Xbee Shield doesn't allow my Xbee radio to sit flush to the shield as shown below:

However the red light on the shield flashes once I lay the Xbee radio into the shield, as shown here:

I have checked pins 2 & 3 of the radio and they are connected (they are Rx and Tx I believe) yet pin 20 for instance is not connected. Which pins are vital for communication?

Also, here's a pic of the other Xbee connected via USB to my laptop:

It's red light is always on.

I would greatly appreciate any insight as to what I am missing. Thank you!

tl;dr:
Do I need to have a C++ program to send serial from my Windows 7 PC to my arduino?
What pins on the Xbee are vital to communication?