Blackmailed (?) by his little sister into playing an otome game to 100% in order to unlock all the cutscenes for her, a Japanese man engages in a multi-day gaming marathon. The game never decided what it wanted to be when it grew up though, so besides the otome game romance aspects, it has magic, guns, monsters, floating islands, dungeon crawling, battle sequences, flying battleships, giant robots, and a ridiculously hardcore level of difficulty. In fact, the only way our nameless protagonist can beat the game is by dipping into the paid DLC for powerful weapons. Exhausted and hungry after enduring all this, the protagonist heads to the store for some food…and falls down the stairs outside his apartment and dies. Naturally, he reincarnates in the world of the game as what amounts to a nameless (well, his name is Leon) background character who never appeared in the game. It’s a setting dominated by upper class women who treat men (and women of lesser status) like dirt. Faced with dire circumstances (he’s to be the victim in a horrific arranged “marriage” / murder plot), Leon sets off to change his fate by exploiting his knowledge from the game and seeking out the location where an ultra powerful DLC weapon is hidden. Did I mention the postapocalyptic backstory that the game didn’t reveal?
This episode features exactly the sort of a dark comedy I expected after having read the light novels. If you can get past all the dark parts, the story is hilarious. Of course, sometimes the more horrifying aspects of the story and setting do detract from that, as does the fact that Leon is more an anti-hero than hero…but this anime has the standard comedy-anime-adaptation-advantage: art and sound! As I have often found with more comedy-heavy stories, the episode benefits a lot from being able to visually and aurally depict the characters in all their exaggerated, overwrought silliness, thereby undercutting the risk of taking things too seriously. The story will eventually delve into adventure, romance, drama, political intrigue, war, social engineering, etc., but I think whether or not you like this series all depends on your ability to tolerate the dark aspects and appreciate the humor.
Trapped in a Dating Sim is streaming on Crunchyroll.