… so is he just recreating a pre-technology reality, but virtually ?

Asking the important questions right here.

Totally agree, but unless you’re comfortable asking which one the person with the problem would prefer, it can be challenging to know which path to take.

I guess you could argue that if you’re not comfortable enough with this person to ask, then the person might not be comfortable seeking solutions.

My relationship with my spouse massively improved when we started telling each other which we prefer for each situation.

In my opinion it’s a needless extra step. I have had my card number compromised before and it was very little hassle to get a new card and my out of pocket was $0. Debit cards would be a completely different discussion however.