Display of Apple5 watch stays black until I press the side dial
Face of Apple Watch 5 stays black unless I press the dial
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Have you enabled Raise to Wake in Watch Settings? Apple Watch App on iPhone > My Watch, lower left > Display & Brightness > Wake on Wrist Raise
You should also be able to tap the screen itself to wake the watch.
And if this doesn't work, check in Control Center to make sure you don't Theatre Mode turned on (two mask faces). If you do, turn it off. Open Control Center by swiping up for the bottom of the screen.