What a disappointment. Stripped to the essentials, the plot seems promising. A gamer that can beat any dating sim has to use his skills to make women fall for him IRL. All I can say about that is that the plot really does not exist. Each main girl is conquered in sequence over the course of 2 episodes and is then never seen again in the story, with no continuity between any of the sections. It reminds me of a bad VN adaptation from the early 00s, where they would adapt one route over the course of 2-3 episodes and then simply move on to the next route without explanation, even if it retconned events from the previous route. It makes the whole thing feel... weightless I guess. Like things are happening but there's no point to any of it, because once a girl is conquered, her part in the story is over and you'll never see her again.
This could be forgiven if it instead tracked the personal growth of Keima, the main character, over the course of these different relationships, but it emphatically does not. The Keima you see in episode 1 is identical to the Keima in the season finale. If anything, he may be even more pathetic. But rather than use the setup of the story to teach Keima that real relationships don't work like dating sim routes, it simply validates his every opinion and impression. In the world of TWGOK, real life is exactly like a video game and real girls will fall in love with you if you say the right line at the right time just like in a dating sim. It's a depressingly cynical vision of humanity and romance that views women as automatons programmed to respond to certain lines if certain conditions are met. You can be an arrogant prick with no friends like Keima and spend all your time gaming and being an asshole and still get the girl if you know the right cheat code to unlock her heart like in your favorite video games. If Keima were pathetic and the series acknowledged that, I think it would be fine, but the story itself instead portrays his worldview as largely correct, which makes it hard to enjoy.
And again, I think this would have all still been salvageable if it were at least fun or had good characters. However, Keima is an unlikeable bore and the 4 girls he conquers are all eminently forgettable. His attempts at romancing the girls are cliched by design, but in a different story, that could be interesting, if he had failed by doing that and needed to grapple with the difference between video game girls and real girls. Alas, as mentioned above, that doesn't happen a single time, the dating sim pickup lines are always 100% effective,. Elsie, Keima's demon sidekick, is one of the few positive things I can say about the series. She's cute and provides most of the few laughs, but isn't enough to make it watchable on her own.
The one other positive thing I can say is that the animation is quite good when they decide to flex. It looks very nice, especially given that its more than 10 years old as I write this, and has strong character design overall. Still though, that's just a fancy coat of paint over a rotten foundation and isn't capable of making up for the huge deficiencies in writing and pacing that make TWGOK an easy decision to skip.
