I ran into my boss (not literally) at the grocery store and it was awkward.
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I’m an employer and I’m friends with all my employees! It’s easy for me to keep the relationships clear and free of inappropriate issues.14
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Oh, yeah, friendly with.
I've had a team lead come out to my house to help with my car, I've gone to their place to deliver extra plants.
My other boss and I hang out sometimes, but she's no longer my direct boss.
And my old boss offered to run groceries to all his team when COVID first hit and we were all working from home.
I find it somewhat awkward to recognize some bosses outside the workplace, but generally I enjoy having a friendly relationship with them outside of work.
I spend most of my time with these people. It's better to be friendly, if not outright friends.