I really like the idea, and I would be interested depending on the subject matter.
While I have been mildly curious about the enormous success of 50 Shades, da Vinci Code, NASCAR & pro-wrestling... I'm relatively happy to conclude my disdain in the face of their otherwise widespread popularity is mostly likely based on simple preferential differences from my own non-typical mind, and the fact that lots of people like stuff about sex in general, murder mysteries/conspiracies, fast cars & muscle-y violence with soap opera-esque elements. I think I get why people like them a lot, and why I'm rather content to feel otherwise. Different strokes and all that...
I do like the proposed concept, however. I think it is a great skill to be able to "get behind another person's eyes" and go through the exercise of piecing together what it is they see in a given interest/pursuit/belief/lifestyle/etc. You may find something new that you really enjoy. And/or you may come to develop a more keen ability to empathize generally.
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By the way, one suggestion for this project would be Jeff Dunham. I'm mesmerized by his success-to-funniness ratio. For me, he is the Anti-Comedian... but people love him.
I think it would be a useful rationality exercise to take something that millions of people love, that you have contempt for, and sincerely try to appreciate it. The purpose would be to get practice imagining a different point of view, and to see whether you're able to do so.
50 Shades of Grey might not be the best choice for this exercise. I haven't read it. Maybe a better choice would be The da Vinci Code, NASCAR, or professional wrestling. But a book has a definite length that you have to get through to be allowed to say that you honestly tried.
The idea is to start a thread for people to discuss 50 Shades, or something else perceived as trashy, and try--not to find what you might like in it, but to get inside someone else's head and imagine why they might like it. (Of course it could backfire, and leave you less open-minded than before, if you always conclude that your contempt was simply right in the first place.)
I think the biggest problem is that if people succeed at finding something to appreciate in it, they would feel terribly embarrassed to say so. So this can be done with alternate accounts.
Anyone interested? What do you hold in contempt that you might be willing to take a closer look at?