I recently read Lolita and was really conflicted as to whether I liked it or not. In one sense it was an uncomfortable read but I found I couldn’t put it down. I see a lot of people saying that they hate it because Humbert is such a monster but surely that’s the point? Nabokov makes it such an uncomfortable read through putting it in first person; we are meant to slightly sympathise with Humbert (because of his unreliable narration) and then feel disgusted with ourselves. Combined with the ‘American Dream’/Academia/Psychological Thriller aesthetic it’s almost as much a mockery of society and its romanticisation of crime as The Secret History. This is even proven by Lolita’s resurgence in popular aesthetics and romanticisation.
I don’t see the connection between Dolores as a name and chess. It’s just a name that literally translates to dolorous, as you said, but it just means grief or sad not sweet.
I mention chess to underline that he liked puzzles. His obsession with puns is the most famous aspect of nabkov’s style: (“If you’re a fan of word play, you probably already know how much fun Nabokov had penning Lolita. There’s hardly a page in the novel that doesn’t make good use of a pun,”)
“Nabokov’s Lolita abounds with puns and ambiguity. The author uses different types of this stylistic device: his writing includes allusions from Classical and Renaissance categories to contemporary humorous play on words[1]. According to Lokrantz, Nabokov’s puns can be divided into five categories…
Thematic - puns used to highlight a theme from the book. EXAMPLE: the author uses many levels of meaning when playing with Lolita’s name. He employs many plays on her Christian name - Dolores, her nicknames - Lolita, Lo, Dolly, and her surname - Haze: doleful days in dumps and dolors[4] my dolorous and hazy darling[5] Explanation: Doleful, dolorous and dolors are plays on the name Dolores and all of them are related to pain and suffering. Lolita’s name was not chosen by Nabokov accidentally; it indicates the girl’s sorrow from the very beginning of the novel.”
https://en.m.wikiversity.org/wiki/Introduction_to_Vladimir_Nabokov's_Lolita/Puns