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Headset keeps breaking

I have HTC phone. I've used both the stock HTC headset and a $20 Maximo one from eBay. Both of them broke after a few weeks.

By 'broke', I mean sound would come out of only one ear. However if I wiggle the wire near the connector on the headset around a bit (see pic), sound would go back to coming out of both ears. But if I let go, it'll go back to coming out of one ear.
https://lh4.googleusercontent.com/-JXuC-w7ijNA/Tj3v49sPpyI/AAAAAAAAAKo/53fIbQRYK_A/IMAG0004.jpg

I know it's not a problem with the headset jack. And I'm pretty sure I know what causes the problem - I keep my phone in my jeans pocket. So when the headset is plugged in, the wire near the plug of the headset gets bent/squashed against my jeans pocket. I think this is causing the wiring around the head of the headset to be damaged, causing this problem.

Is this a common problem? Or is this mostly likely to do with me using cheap headsets? I'm interested to invest in a decent headset (up to $100, preferably less, has to have at least one control button) as i spend a lot of time listing to music on it or answering calls (~1-2 hours a day), but I don't want to spend a lot of money on an expensive headset and having this happen too.

Like, does anyone else have this problem? Or is it really something that I am doing wrong. I do have a case + holster for my phone, but I dislike using it because it's bulky. Should I just not have my phone in my pocket, when I'm walking around and the headset's plugged in? Is it time to try and find a decent, lightweight, stereo bluetooth headset? (not sure if these even exist...)
 
Actually, I was going to suggest a stereo bluetooth headset. And yes, they do exist. You need to make sure that your phone has AD2P capability, though. If it doesn't, it won't play music through the headset. If your phone is less than a year old, I'd imagine that it does. As for where to find them, any of your big box electronic stores will have a selection. I've never bothered to use them, since I'm a truck driver and the cops tend to get a little irritated if they see me rolling down the road with a pair of headphones on (Can't imagine why). But, I've talked to several other people that have them and they all say they work quite well. i've seen them at truck stops for 100, so I'd bet you can get them the same or a little cheaper at a regular store. Just google 'bluetooth stereo headset', and you should find several.
And according to the drivers I have talked to, they switch from music to a call with no problems, and they don't seem to affect their hearing while driving, if they aren't listening to music through them.
 
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