Quiz about a very famous literary work or two (& Samantha Bee in Trump Country)

I am thinking of a work of literature which fits each and every one of the following 37 (+1) clues, from the macro scale all the way down to the micro. What is its title, and who wrote it?

[Amazingly, the answer also pertains to Samantha Bee's word for Ivanka Trump]

1: The work is one of the most famous and popular works in literature, even though it was written centuries ago.

2: The work is filled with famous, witty epigrammatic quotations, which pop up regularly in 21^st century popular culture; many of the best ones are spoken by the witty, brilliant protagonist; and the rhetorical device of hendiadys is prominent.

3: Conversely to #2, the work also has an iconically tedious character: a verbose, sometimes nonsensical  parent who criticizes the daughter-heroine’s courtship behavior, and is also disrespected by the hero.

4: The work is set in a period of war, with the protagonist’s home country under threat of invasion from a powerful hostile neighboring country.

5: The work is famous for its multilayered ambiguities; in particular, the protagonist is plagued by persistent doubts about the guilt or innocence of another major character, until those doubts are eventually and dramatically resolved.

6: The heroine is one of the most famous and popular heroines in literature.  

7: The heroine is a young woman with a doting father.

8: When the heroine’s sibling travels to an exciting city, questions are raised as to the risks of the sibling’s misbehavior, while there without parental supervision.

9: The hero is one of the most famous heroes in literature.

10: The hero’s father, whom he speaks of idolizingly, is dead when the work begins.

11: The hero is 28-30 years old, about a half dozen years older than the heroine.

12: The hero is high in status, and much higher in status than the heroine.

13: The hero has had a university education.

14: The hero is often accompanied by a close male friend, who is extremely deferential to the hero.

15: The hero is moody, withdrawn, and taciturn, before undergoing an apparent shift for the better.

16: The hero makes a famous generalization about each person having one particular natural defect.

17. The hero experiences an ambivalent attraction to the heroine, and other characters speculate about this, including about the obstacle posed by the large difference in status between them.

18: The hero engages with the heroine in famous sexual repartee, focused on the word “country” (a la Samantha Bee vis a vis Ivanka Trump) and the word “nothing”.

19: The hero also makes a risqué bon mot about the heroine putting on a sexual show for a group.

20: The hero is very focused on the poetry of love.

21: There is a foil to the hero who strongly resembles the hero in some key characteristics, and who is in conflict with the hero at times during the story.

22: The heroine receives a letter (the full text of which is presented in the work) from the hero, written to convince and explain to the heroine she has misjudged his worthy intentions.

23: There is reference to a duel.

24: A devious plot by the main villain is ultimately foiled by the hero’s proactive intervention.

25: The word “merry” is used in relation to sexual license.

26: The word “philosophy” is used in a generalization by a lead character about how to think about life.

27: The exclamation “Heaven and earth” is used in a famous passage referring to ghosts.

28. There are repeated occurrences of surprising haunting encounters.

29: The word “pollution” is used to referred to the dead.

30: The death of a father is a major plot element.

31: The protagonist utters a heartfelt speech expressing strong disillusionment with the human race.

32: There are repeated references to drunkenness.

33: There is sexual punning on the word “private”.

34: There is sexual punning on the word “instrument”.

35: There is punning on the word “desert/deserve”.

36: The protagonist gazes adoringly on a portrait of a beloved man.

37: There is reference to protesting against a second proposal to the same woman.

BONUS CLUE (there’s a huge reason why I’ve set this clue apart from the first 37 clues):

38: Its hero stages a “play” involving performances by others at his direction, with the specific goal of provoke another person (whom he’s obsessively focused on) to reveal a character.

Things are not as they might at first seem in this quiz, in particular re Clue #38…. After receiving any answers, I will, as usual, reveal my interpretation and explanation thereof.

Cheers, ARNIE

@JaneAustenCode on Twitter