Henry Clinton was Jem’s best friend, so he has had a close relationship with the Finch family throughout his life. Though the Clintons are a fine clan, Henry’s family isn’t quite as upper crust as the Finches. Alexandra is very concerned with Henry’s family, especially when he gets discussed as a potential husband for Jean Louise. Henry’s background is perfectly acceptable for him to serve as Jem’s best friend or Atticus’s law partner, but when it comes to marriage, he is not quite of the Finch tribe, so Alexandra does not wholly approve.
In many ways, Henry Clinton fills the textbook definition of a “good guy.” He treats Jean Louise like a perfect gentleman. Although he flirts with her and makes his intentions to marry her very clearly known, he never tries to trespass his boundaries. He courts her when she is in Maycomb and he frequently proposes to her, but he lets the relationship proceed at her pace, never giving her any firm timeline or ultimatum. When Jem died, Henry gracefully and compassionately filled the role of surrogate son for Atticus. Henry became Atticus’s junior partner in the law firm, and Atticus trusts Henry deeply.
When Jean Louise and Henry were children, Henry only really figured in Jean Louise’s life as Jem’s friend. Jean Louise’s primary male friend when she was a girl was Dill Harris, who only came to Maycomb in the summertime but was inseparable from the Finch children from the moment he arrive to the moment he left. Henry isn’t jealous of Dill, per se, but he does seem to wonder sometimes if that relationship could have developed into anything deeper.
Jean Louise and Henry became closer when Jean Louise entered adolescence and they began to interact as a couple. Now, most of the town assumes that Jean Louise and Henry will probably get married. However, Jean Louise isn’t really sure whether or not she’s in love with Henry or whether he just represents a nostalgic relationship from her past.