You americans and your precious craigslist. Electronics, cars, furniture, and sex. It's the Walmart of the internet...plus sex. Look anyway, here's a thought.
Head over to personal/classifieds section of (your local) craigslist. Go email a few people, when they start asking for pictures send pictures of your friend. When they ask for a name, lie and make one up. Hell, even better if you know where your friend will be that night (say a coffee house or something) you can even say "Oh yeah, we'll I'm going to be heading to this starbucks on..." etc.
Think of this as a really mean blind date. Because someone will no doubt run into your friend, call them by the wrong name and then have it out with them about their "true" identity. It'll make for awkward conversation all around. What's more is you could actually be present at said event, and play the whole thing off like you had no idea what was going on.
This kind of challenege works best in a small, possibly college town. Huge places like Chicago and other large cities have lots of people trying to make a quick buck and will scam you of pictures at the least if they can. The fear here being...
*** WARNING *** - craigslist from what I'm told is a dangerous place, from what a good friend in network engineering tell me: photos are sent, and then reposted for other ads/services on CL. Hence i said the bit about the made up names. Make sure the people you are talking with are real and above all else SANE.
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