I tried everything.
Changing Mac password
Disabling/enabing Handoff
Unpair/repair Watch
etc.
None of these helped because my Mac was looking for some outdated token on my Watch.
Finally reached out to Apple support. This worked:
1. System Preferences > iCloud > turn off Keychain
2. Keychain Access > Preferences > Reset My Default Keychains
3. Reboot Mac
4. You'll be asked to enter your iCloud password - enter it, then give iCloud time to sync up.
5. System Preferences > Security & Privacy > Click the lock to make changes (ensure it's UNLOCKED - if it already is, skip this step)
6. Check Allow your Apple Watch to unlock your Mac