Ear buds. The headphones never seem to fit, always fall down or are otherwise uncomfortable. Sometimes, they get tangled in my hair. The really nice ones that cover the whole ear and give great sound always end up in a fight with the bows of my glasses, and make my glasses uncomfortable to wear.
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I have learned to sleep with music, Pandora on my iPhone, and I use really comfy padded ear buds for that purpose.
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-- Steve finds he also tends to kill his earbuds; the last pair was from Sennheiser and It stung to accidentally wreck $99 hardware.
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