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that's funny, you go regularly to demo stuff, shopkeep must really like you.
but no, you are used to low end stuff. demoing just means you tried them for 15 min. you only really begin to understand why you like a pair of cans after a while of listening which i would say is a few weeks of listening for a couple hours a day.
So, applying this to a car, does one truly have to drive around a geo metro for weeks to figure out that they like it? Do they have to drive around a Lamborghini for weeks to figure out if they like it?
What about a chair? Does it take weeks to realize why you like or dislike it?
I'd like to put forth the theory that things can be judged when you experience most of what they have to offer. It may take a long time to experience a car in most every condition one will encounter. Not so with headphones.
I think that, concerning headphones, a direct comparison to another with several songs from the various genre's would be sufficient for one to say that they had 'experienced' it enough to decide whether they liked one compared to the other.
If we are talking about maturing tastes, I think that is a different argument. If someone is used to a bass heavy sound, precise things like Etymotics or the AD-series by Audio Technica will sound bright and disturbing. On the other hand, when I first listened to an Etymotic Hf5 over a few days, I initially recognized that they were more detailed than my previous headphones... I just didn't prefer it.
I understand why I like a particular 'phone almost immediately: It sounds appealing to me. When my preferences change from higher end experiences, it's the same. Why do I like a 'phone? Because the sound appeals to me. I don't think time is a main part of understanding a headphone. I think it's an exponential downward curve concerning the determination of whether someone understands whether or not they like a pair of 'phones.