I have a reverse-like story where Im the non-audiophile, or I was:
Back in the day, we had at home a pair of vintage JVCs which were good (or thats what I remember), but I was used to the speakers, later then I bought my first iPod with the very original earbuds (first ones), and started to like them... Years later, I dont really minded about better quality headphones, I was kind of gamer who earned money winning tourneys and stuff, got to try a lot of gaming stuff which I didnt like over my Apple Earbuds but suddenly, one guy showed me the Sennheiser HD555...
Almost 7 years from there, here we are!
Other stories:
Some friends, and girl friends come to my home and while staying, they see my gear and want to try it, some are surprised (usually by the DT770s bass) or not, others by the DT880s clarity and trebble, and many others by LCD-2s sound signature, but this girl, friend of my sister who likes rock music wanted to try the gear, and her face was a poem xD
This other day, I was walking through the streets with my Grado SR80i (yes, I use em as portable headphones xD), and came across a friend, who asked me about "that vintage looking headphones", I was listening to some punk stuff which he liked, let him listen and MAGIC! He bought a pair just the following week, the first thing he said was "oh god I hear the music around my head, not inside!!". Despite Grados arent known for having a very expansive soundstage XD