I'm a side sleeper too...and normally I'm not bothered by having the earbuds in my ears. One thing I have done if my ear was bothering me was just put one earbud in and leave the other one out. It works for sleeping if the earbud out is the one on the side I am sleeping on...but not so much if it's reversed. Always better with both in for me. I would suggest trying different things too...different types of music or even audiobooks. The idea is that they're calming and distracting from the pain...which means that I fidget less (I'm prone to tossing and turning too). I usually start listening before I'm ready to fall asleep so that I'm already "in the zone" by the time I'm ready to lay down for sleep. Just be careful with books and don't listen to anything that will get you riled up or even anything new that you are SO into that you don't want to sleep...lol...that doesn't work so well for helping you sleep. I have a couple go to books that are among my favorites that I've either read or listened to before...so no big deal if I drift off and miss a bunch of it. :)