Brought a few pairs of nice headphones down to my cousin's house when I visited over my Christmas / New Years vacation. Brought my HifiMan HE-400's and RE-400's, Sennheiser HD558's, ATH-M50's, and Ostry KC06A's. I also brought my O2, ODAC, and a hard drive full of high quality music with me.
I first spent some time showing them my favorites (the HE-400's and the 558's). Both of my cousins absolutely loved the HE-400's, and their friend who happened to be there couldn't believe what he was hearing when he tried the 558's. He loved them so much that I just let him borrow them for a few good hours. He asked how much they costed, and couldn't believe it when I told him that I picked them up for about $90 on ebay. Definitely have a convert there.
My cousins both really want a pair of the HE-400's but can't afford to spend that much on headphones.
The M50's were largely ignored since I started them off with the nicer stuff, but they all agreed that all 3 were a lot better than anything they'd tried before that night.
No one was really that excited about trying the IEMs, but my cousin did end up trying the Ostry's and said that they sounded really good, but preferred what we would call the soundstage of the HE-400's.
All of them remarked on the soundstage of both the open cans, and both of my cousins were astonished by the clean bass response of the HE-400's. They'd never heard "bass that sounded that good." Their friend just absolutely lost his mind when I played him part of the album "No Drum and Bass in the Jazz Room" by the band Clever Girl. That album is great at showing off the strengths of the 558's. He was left quite literally speechless. The friend and my younger cousin both loved the comfort of the 558's as well. The older of my cousins, though he doesn't care much for IEMs, did remark that he was surprised how detailed the KC06A's were.
All in all, it was a great success. 2 cousins that realize how great headphones can really sound, and one full convert that's looking to pick up a pair of 558's of his own.