Dear ndswim09 - I just had a similar issue. My Bose Soundsport have been working great since I got them a few months ago, but today while they were paired with both my Windows 10 laptop and my iPhone (currently listening to music streaming in web browser on my PC) I walked down the hall too far away from my PC so the Bose disconnected from my PC. When I walked back in my office they Bose would not automatically re-pair with my PC like they usually do, so I went into Bluetooth settings on my PC and deleted the Bose and tried to re-add them as a new device. This is when the Bose would not pair with my PC and it became frustrating. My Bose were at about 20% battery so I'm not sure if a low battery would prevent them from pairing, but after charging for a while they still wouldn't pair with my PC so I turned off bluetooth on my iPhone to force the Bose to disconnect from my iPhone. I immediately tried to pair them with my PC and it worked instantly.
Not sure if it's similar to the problem you are having, but if you still haven't gotten your Bose to pair with your PC try turning off bluetooth on your phone first to make sure your Bose aren't paired with anything else at the same time. Once you pair them to your PC just turn bluetooth on your phone back on and your Bose should automatically pair back up with your iPhone in addition to your PC.
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