The closest thing to a dating sim I've played so far was Baldur's Gate 2, I haven't yet tried any of those Japanese dating sims so that's a gap in my gaming education.
Question: Are there any good ones out there that are really funny? As in so hilarious that you have to laugh so hard that you can't eat food at the same time. In-depth dialogue with reasonably deep and most importantly non-linear gameplay would be my top priority. Not interested in passive visual novel type of gameplay and also not interested in added fluff like Candy Crush puzzle mechanics and mobile flash game item upgrades. As for the art style, nothing wrong with anime but not the pedo kind please so I'll pass on Huniepop & Co. Anime/manga has a wide range of different styles (just as wide as Western comics & animation) so I don't quite understand why the pedo kind is so prevalent, especially in the dating sim / visual novel genre which I assume are aimed at grownup gamers.
Policenauts for example features a style that's still generic anime but without the pedo look, here are some screenshots: