Why is it not possible? There have been countless times where co-workers have booked in time on the calendar (for observability for the team) to meet up with a friend for lunch, or to even meet up after work and support local businesses around their home.

Because it’s not spontaneous what they are doing, it requires planning and coordination in direct contrast to spontaneity with coworkers

There isn’t anything wrong with planning and coordinating, it is simply not spontaneous and has no similarity in energy expenditure and availability

Felt pretty spontaneous to me: "My friend just messaged me, we're going to a new cafe that opened up near my house."

Or is that too much planning for you?

What is the point of your response, in your own words

Re: "1 on 1s walking around the block and seeing this cool cafe that closes at 2pm?"

That does sound nice. All of my in office jobs were sitting at my desk staring at a computer for 8 hours. No one was walking around the block. :-) But that was over ten years ago.