YMMV / Holy Matrimony!

• Crosses the Line Twice: Jessebelle's abuse of James, while not treated as acceptable or okay, is so absurdly over the top that it makes for some of the show's funniest slapstick comedy, especially once she lures James into the infamous "sex dungeon".
• Ensemble Dark Horse: Growlie, James' adorable and loyal Growlithe who saves him from Jessebelle in the episode's climax. Plenty of fans wished that he got to join James and become a series regular.
• Harsher in Hindsight: In this episode, James fabricates a childhood story where he froze to death in the cold as Growlie watched on in despair. Fast forward twenty-years later to Pokémon: I Choose You!, Sorrel reveals during his childhood his Luxray froze to death trying to keep him from freezing.
• He Really Can Act: Being A Day in the Limelight for James, Eric Stuart delivers quite a performance in this episode. Most notable is the scene where James ends up in a game of "Persian and Rattata" with Jessebelle; he sounds absolutely and genuinely terror-stricken running around the room as Jessebelle continuously pursues him with a whip.
  James: (to his parents, who are sitting down and drinking tea amidst the chaos) If you two weren't such lousy parents... YOU'D STOP THIS MADWOMAN!!!
• Jerkass Woobie: Poor, poor James. As if being pursued by a violent lunatic of a woman wasn't bad enough, his own parents don't give a damn about his feelings and are willing to help Jessebelle lure him into a trap so she can make a proper gentleman out of him through her abuse.
• Nightmare Fuel: The infamous "sex dungeon" is made of this, as is Jessebelle's possessiveness of James. While there's a lot of Black Comedy to it, just imagine how scary it is to be romantically pursued by someone who just will not take no for an answer, especially when your own parents are not only insensitive to your terror, but actively encourage your abuser to keep hurting you.
• Unfortunate Character Design: Jessebelle's trousers in her "tamer" outfit have very similar coloration to her skin, which can give the impression that she's not wearing any. The scene's BDSM undertones really don't help.
• Values Resonance: While most of it is Played for Laughs, Jessebelle's "relationship" and treatment of James is not portrayed positively at all. Anyone who was supportive of it (mainly his parents) was also portrayed as being in the wrong. Abuse is abuse, even if it's female on male. Considering this aired in The '90s, where the Henpecked Husband trope was still being used frequently in media unironically, it was an anvil that really needed dropping.
• What Do You Mean, It's for Kids?: The dungeon, Jessebelle's unhealthy obsession with James, his parents' emotional neglect towards him, and the funeral scene (albeit a fake one) all lend themselves to this trope.