I had the original Apple Watch and have now gotten a series 2. I had never tried to pair the watch with BT headphones before and I decided to try last night. I have 2 different pairs of BT headphones (one Anker, one MPOW) and while the watch "sees" them, it will not pair with them. I spent about 20 minutes trying and they never would connect - I kept getting the message that it could not pair and to make sure the headphone are in pairing mode (they were). Obviously, I was only trying one at a time. Are there issues with connecting with certain headphones or is there something else I might try? I have a few BT speakers and I'm going to try to pair with those tonight and see what happens.