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Hi, I am Raffi IT Specialist with 10+ years of experience and welcome to JustAnswer, thank you for utilizing this service. I will be assisting you to fix the issue you are having. May I know what troubleshooting have you done?
Is the Apple watch on the latest OS?
Is the IPhone on IOS 11 or above?
Ok thats good. Can you try the following steps listed here and let me know how it goes: https://support.apple.com/guide/watch/set-up-and-pair-apple-watch-with-iphone-apdde4d6f98e/watchos
Dont skip the update. You want it to be on the latest version.
I think your next step here is doing a factor reset of your iphone.
I think your bluetooth is having issues with the iphone. Have you taken it to the apple store to test?