Find My Notifications Not Showing on Apple Watch 5

I have it set to get a notification when a contact arrives/leaves certain places. they have an Apple Watch SE with cellular set up with Family setup. I receive the notification on my phone, but it's not showing up on my Apple Watch 5. My phones and both watches are updated to the latest OS software. I get all other notifications to my Watch, but not the find My. I do have it set in my watch app to allow Find My notifications on the watch.

Second, the contact gets a notification on his watch every time he arrives/leaves one of the places. Is there a way to turn that off so he doesn't have to dismiss the message? He seems to have an option to dismiss or message.

Thank you.