I have the first generation iPod nano and I listen to it ALL THE TIME. Seriously, I can't live a day without it. But ever since I've gotten it (which was three or so years ago) I've gone through probably six headphones.
First, at some random moment, one ear bud thing will stop working unless I move or jiggle it a bit and then after a couple of days, the ear bud would then die (it won't work no matter what). After a few more days, the other ear bud will do the same thing!
The headphones I use somewhat varies. I used Skull Candy headphones, but that lasted probably four months and I will never use them again because I couldn't hear anything from outside, which was very inconvenient. Two were those Sony ones that they sell for like $10 in Target and one lasted for three months, the other lasted less then a month. And three of the six were those Apple Earbuds (one was a hand-me-down though) and they were the one that lasts the longest (or at least more then four months).
But right now my money is tight so I'm looking for headphones that are both cheap and long lasting!
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