Just jumping in to say I purchased these a while ago and am satisfied, though not delighted, with them. They work okay (or did, I have a 2-week old and so haven’t used them since before he was born), and my head doesn’t tend to overheat (though I tend to trend cold rather than hot anyway). My main complaint would be that an annoying robotic voice starts nagging you loudly when the power is low which is…less than ideal. Still, a lot cheaper than the SleepPhones option if you want to test out the theory.
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Particularly when you’re trying to … y’know … sleep.
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My girlfriend’s Apple Watch used to buzz her in the middle of the night to remind her to “stand up”. 
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I use my Airpods Pro, but not for listenings music or sth., but only to use Noise Cancelling if it is loud outside. It works like a charm since more than half a year, does not hurt etc during sleeping and falls off during the night, just like I want it.
Precisely. That said, if they’re charged it’s generally not a problem. Usually I’d wake up, turn them off and remove them before it was an issue.
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With the AirPods, for me the original earbuds are more comfortable than the AirPod Pros for sleeping. You can’t get some “interesting” feedback effects by blocking orifices on the Pros between ear and pillow.
My uses Beats Flex with one ear in for listening to podcasts and she’s happy with that.
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Like the original poster (OP), I go to sleep listening to podcasts or other spoken word content. I am also a side sleeper. I’ve tried a bunch of different headsets, both wired and wireless.
TL;DR: The Beats Flex headset from Apple is by far the best solution I’ve found.
- Very small earbuds that are reasonably comfortable even when sleeping fully against them. (Far more comfortable than AirPod Pros, which I’ve also tried; regular AirPods fall out of my ears.)
- The earbuds sit far enough inside your ear that sound leakage doesn’t bother your sleeping partner. But not so far as to poke or irritate folks who don’t like in-ear canalphones.
- The cabling system that connects the two earbuds is minimal enough that you don’t get tangled in it. (And no cable to your sound source at all.)
- But it’s enough cable that you won’t lose them in your bed. Even when I wake up with one or the other out of my ears, they’re just a twitch of my hands away.
- The Apple W1 chipset makes switching between my iPhone and iPad easy, if not effortless. (Certainly, it’s far less likely to frustrate and wake you up than other Bluetooth headsets.)
They are not flawless. Some downsides:
- Their predecessor, the nearly identical BeatsX, were fragile. Even though I am careful with my things, I managed to destroy two pairs in just over a year, exclusively using them in bed or commuting by train. I haven’t had the new ones long enough to comment on durability, but they do seem like they’re a bit better made.
- The on/off button is egregiously non-tactile. You have to watch for the light to come on, or listen for the on tone, to be certain you’ve actually turned them on. This irritates me literally every time I turn them on.
- They’re not as cheap as wired headsets. Though at $49, they’re ½ or ⅓ the cost of the BeatsX, which were $150 at launch and fell to $100 later.
- The sound quality is great for spoken word, but falls short for music. (Tastes vary, but just this afternoon I was listening to a few songs from season two of Altered Carbon, and was disappointed with the lack of depth/richness, compared to my AirPod Pros.)
I would love to give the Bose Sleepbuds a try…once they make a version that connects to my phone and iPad. They look like the first truly good, purpose-built headphones for sleeping. (I’ve tried SleepPhones, and they were awful.) But not playing my content is a dealbreaker.
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That’s really good info - thanks! For $50, that might be worth trying. Do you find the battery life in practice is pretty much as advertised? It feels like you might only need to (practically speaking) charge them once every couple of days?
This just popped up as a promoted entry on Reddit while I was searching on a completely unrelated topic. No idea if they’re any good, but another option.
Personalized advertisements? 
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I charge mine every day, plugging them in when I get out of bed. Even though this headset is pretty much dedicated to sleeping time, I found that trying to go two nights on one charge resulted in running out of charge before the 2nd night ended.
I might have more insomnia issues than you do, though, so YMMV.
The rest of this is speculative, as I haven’t done any actual testing. But it seems like the headset puts itself to sleep relatively quickly the first time your device stops playing audio (e.g., when your sleep timer expires), but if you turn the headset back on during the night, it doesn’t go back to sleep as quickly when no audio is playing.
At least, if I wake up in the middle of the night, I almost always need to turn the headset back on. But if I wake up a second time, but still a few hours later, the headset seems to still be on.
I dunno, I don’t want to wake up enough to capture metrics on this, so this is just an impression. Would be interested if anyone has any actual info here.
Personally not a fan of the sleeping headsets with a headband. If you can sleep with something wrapped around your head and covering your ears, great. It irritated the heck out of me when I tried using SleepPhones. They had several other issues, and I abandoned them long before I got used to the headband. YMMV.
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I used to use sleep phones, but they don’t block the sounds of the chainsaw operating next to me all night, so I’ve just been using my QC35. They don’t stay on all night, but neither do AirPods or any other solution I’ve tried, including sleep phones. I use a neck pillow to help stay on my back, so that helps.
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So a HomePod should work great. It will stay on all night, be super comfortable for you, and stop the chainsaw. 
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Jam a couple of HomePod minis into a SleepPhones headband and we have a winner.
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My daughter actually will nestle in with the Homepod to keep listening to music after bed if we let her. 
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