In a recent episode of The Talk Show, Ben Thompson talked to John Gruber about the problem with John’s watch disconnecting with his phone. Ben asked what pocket John keeps his iPhone in. This led to a discussion as to whether or not keeping your phone in the pocket opposite from your watch-bearing wrist causes a connection problem. As Ben explained, your body is a bag of water and by putting your wrist on the opposite side of your body from your phone, things get more difficult.
From personal experience I can confirm this is the case. I always carry my iPhone in my left pocket and wear my watch on my left wrist. I’ve never had any connection problems. Recently I had a pair of jeans with a hole in the left pocket. So for a few days I ended up carrying my phone in my right pocket. My watch disconnected from phone more times over those two days then I’ve had in the entire time I’ve owned the Apple Watch. If you’re carrying your phone in the opposite pocket from your wrist, you may want to rethink that strategy.