Lord Chesterfield, as a teacher, philosopher, professor, and eternal learner, believes in a different approach to the dynamics that often take place between parents and their children. These are much different in Lord Chesterfield's time where parenthood was more like the assurance of lineage rather than a growing relationship of mutual affection between both sides.

In the many letters to his son, Lord Chesterfield lovingly expresses his desire to be his son's guide, his teacher, and his mentor. He also admonishes his son with love, rather than contempt, when he sees him going into the wrong steps.

In the letter XX published in London and dated November, 24, 1747, Lord Chesterfield writes a beautiful message of concern, advice, and admiration that clearly denotes what his views are on the relationship between parents and their children:

True friendship requires certain proportions of age and manners, and can never subsist where they are extremely different, except in the relations of parent and child, where affection on one side, and regard on the other, make up the difference. The friendship which you may contract with people of your own age may be sincere, may be warm; but must be, for some time, reciprocally unprofitable, as there can be no experience on either side. The young leading the young, is like the blind leading the blind; (they will both fall into the ditch.) The only sure guide is, he who has often gone the road which you want to go. Let me be that guide; who have gone all roads, and who can consequently point out to you the best.

Basically what he states in this portion of the letter is that he understands how sometimes young people, in the interest of being well-thought of and popular, often tend to follow the advice of their friends, and not the advice from their parents. To this, Lord Chesterfield responds by saying that a father and a son can be just like friends: They can advice each other, support each other, and this is because they have each other's best interests in mind.

Lastly, he offers his son the chance to establish a bond of friendship, and to trust each other as such. He knows he can tell him what is best for him, and that his son would reciprocate in the same manner.