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On the subject of headphones while riding, can I possibly sway you by telling you about bone conduction? My sweetie got me a pair of Shokz for Christmas as an “I don’t know, maybe??” present and they’re amazing. There’s nothing that goes inside your ear, instead two little pads on the front and back make contact with the bones in your skull and vibrate your music. You can hear everything around you perfectly clearly and the audio quality is shockingly good, and nobody else can hear what you’re listening to. They go over your ear and behind your head so they’re comfortable if you’re a sensitive baby like me. They even have a microphone so you can take a call (and talk without screaming because you can hear yourself)! Meant to be safe for running, walking, and biking, best random gift ever!

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