So over the last year I've been trying out a few of these headband headphones. They all had their weaknesses except this one. Those with wires have obvious issues, BTs with square speakers are extremely uncomfortable sleeping on your side, and most BTs have short battery life. I have an older version of this product that works fine except the battery life didn't seem to last long. It will take long enough for me to fall asleep, but it will be dead when I wake up late at night, which I always do. After trying a few of the alternatives I figured I'd just buy another of the earlier versions and take one to sleep and one when I wake up in the middle of the night. I was very surprised to learn that the battery in this upgraded version not only lasts all night, but also for several days before needing to be recharged (I unplug the headphones in the morning). Also, I set the audiobook on my iPhone to play for 30 or 45 minutes when I go to bed and wake up at night, so it's possible that these improved headphones have a sleep mode when nothing is coming from the iPhone. In any case, the headphones are charged at least 60% after 5 days. Since I had the new version, I didn't use the old ones at all. And as others have pointed out, the thin drivers, overall design and padding make these BT headphones very comfortable for side sleepers.
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