You know, you could offer to help him, but maybe not with the kind of help that he originally had in mind. Ask for a list of the software titles he wants help with and return him a disk full of high quality open source and freeware alternatives.
Explain to him that this software is good, needs no cracks, and doesn't come loaded with malware...and best of all, it's legally free.
Ask him to do a favor for you...that since you bothered to take the time to create this collection for him, he should bother to take the time to try every single application on your disk.
Because if you don't help him in some way, he will find someone else that will. And they are likely to do exactly what he asked you for. And if you can do this before he asks someone else, maybe he will still ask someone else, but maybe he won't pirate
all the things he originally planned on.
If he keeps just one of the free apps and uses that instead of pirating something on his original list, consider it a partial victory, and maybe it will make him just a little more open to the idea of using free
legal alternatives in the future, if he doesn't feel like paying for it.
Or you can prepare the disk and then clean the malware off his pc and install everything for him, placing the shortcuts on his desktop like this:
- OpenOffice (MS Office)
- GIMP (Photoshop)
- xchat (mIRC)
- etc.
That way he knows what he has and what it compares to when he wants to accomplish a task, and he won't get lost trying to figure out what all that new stuff is.
