Key secure enough?

Alright, perhaps someone can settle this debate for me. A friend of mine is convinced that the Cool Encrypter at http://www.seabreezecomputers.com/encrypter/ is uncrackable. I'm pretty sure that because the encryption process is known, and you can see the program repeating the key as it goes, that someone who knows what they're doing (i.e. not me ) can piece it together pretty quickly.

So here are two seperate strings I am sure can be decrypted; but he's pretty sure that even if the encryption process is known, you really can't crack the Cool Encrypter. Can someone settle this one way or the other?


~)yivGQxaK;10tgJ9A8o[>Qx]]fAbaRT6#?lw


\$fcD^${X)#XQ2:GD7Ztc5Q7rW\3HTt-VnH;%8ki

He's pretty sure he used a secure key for each, but his idea of a "secure" password is a word he can remember

Is anyone interested in helping me figure out the keys on this to prove him wrong?