If wearing the mask reduces risk of disease spread (such as at the grocery store) it does not look irrational. If wearing the mask does not reduce the risk of disease spread (such as in your bedroom), it does not benefit the public good.
The same if conditions apply; the specific answer depends on circumstances. Is your friend elderly? Do they socialize a lot? Do you embrace, or maintain distance? Do you spend a lot of time close together talking? In the kitchen or on a breezy porch? It is rational to do things that benefit the public good (at reasonable cost). How could this not be the case, if someone is not a predator or parasite? We are the public, we benefit from a healthy public.
Caplan is 49 years old and in apparent good health. There is little risk* that COVID-19 will affect his personal health, whatever his behavior. *EDIT: little risk, relative to other risks that he already accepts, such as driving a car or drinking sugary soda. How is it rational for him to buy and use gloves for grocery shopping, if not to reduce the risk of spreading disease to others? I'm not sure I understand what you mean by generalizing. His behavior is to become informed about the risks and make carefully calculated, emotionally neutral decisions that balance the positive and negative consequences of his choices. I would like to see that pattern generalized. His specific choices (on restaurants, or gloves) are tailored to his individual situation and preferences, and should not be generalized. Note that Caplan does not pretend to have all the answers. Admitting to confusion, he points out the value in relaxing behavior and restrictions to measure the risk that comes with a more open posture. A more effective and ethical approach might be paid voluntary human experimentation to improve our understanding of the risks.