Well, that certainly sucks to put it mildly. Hmmm....I've looked around in terms of shareware and stuff, and there's not really too many options. The only other thing that might work but wouldn't be cost effective is to look at mobile audio interfaces from a company such as M-Audio
They have some fantastic products that might be able to serve your friend's needs. However, as I mentioned earlier, it would be costly and probably run upwards of a couple of hundred bucks. And that really wouldn't be worth it just to get a second set of headphones working unless they'd get alternate use of the audio box. Sorry I can't help much more than that. Hopefully a computer savvy audiophile may be able to help out with this dilemma.