I had the same problem. I went nuts making sure I had updates on both watch and phone. reset the watch and kept adding it though Bluetooth. this is one phone I went nuts with to fix and set every setting that pertained to me. here's another thing Samsung told be to do through chat. make sure battery is full. this ran for an hour before I saw nothing happen. I finally got my Samsung 3 watch to work. Can you try these steps please: Turn off the device. Press and hold the Volume Up key and the Bixby key, then press and hold the Power key. When the Android logo displays, release all three keys. An 'Installing system update' message will show for 30 - 60 seconds before the Android system recovery menu options appear. Press the Volume down key several times to highlight wipe cache partition. Press Power key to select. Press the Volume down key to highlight yes, them and press the Power key to select. When the wipe cache partition is complete, Reboot system now is highlighted. Press the Power key to restart the device.
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