My Answer: What should you bestow? Whatever your friend desires! When? Immediately. (After all, when you love someone, you want to fulfill them right away.) To whom? To everybody!
If you come out of yourself, then the distinctions between whom to bestow to disappear. Whether it’s a friend, the Creator or all humankind, outside of your egoism they are all one.
Baal HaSulam writes the following in Item 15 of the article, “The Revelation of Godliness”:
“It is because indeed, with respect to a person who is still within the nature of creation, there is no difference between the love of God and the love of his fellow person. This is because anything that is not him is unreal to him…
Hence, he defined it for him as love of his friend because its aim is nearer and is revealed faster, since it is fool-proof and is demanding.”
It follows that testing how much you love your friend is a sure way to avoid mistakes on the path to revealing the Creator.