This is the main point of Experimental Comic Kotone. It ends up failing in an epic fashion. The World God Only Knows takes this to metafictional levels, featuring a Dating Sim otaku who captures escaped spirits by applying his knowledge of dating sims and their sub-genres. Done as a joke at a comicon in Japan, where Studio Pierrot showed a redubbed set of Bleach clips meant to be an advertisement for an upcoming dating sim.
There's two 'dates' in Metal Gear Solid: Peace Walker , where you can go to the beach with either Paz or Kaz. You speak to them using the Co-Op battle cries, and then if they like you you can invite them into the cardboard box for quality time.
They're parody, but both Paz and Kaz have different personalities which come out during the dates Paz likes being complimented and treated gently, Kaz likes being punched and Big Boss staring at his crotch with the binoculars. It's mostly just them saying "Duh", occasionally pausing to talk about how awesome Strong Bad is. The fourth episode of the Haiyoru! Nyarani short flash animation. Nyarko is seen playing Lovecraft Plus. It's an Inverted Dating Sim , the character has SAN among the character's stats , which measure your resistance to the Yanderes who are after you.
Lose enough SAN and you end up with her forever, wallowing in your mutual insanity. The eighth episode of the television anime has the cast stuck in a cursed dating sim , and they will only escape once Mahiro declares his love for one of them. He is reluctant to do so , so it works out as an inversion as above.
A Yuria Shiki omake features the Yuria Shiki eroge. The first options all immediately lead to a sex scene except for the youngest female character, which immediately leads to the player getting arrested as a pedophile. The Journal Comic Doodle Diaries featured a short parody of dating sims, starring the three main characters as the love interests.
Date A Live plays this straight with the twist that the protagonist doesn't make the decision making part. Rather, it's his sister and the Ratatoskr crew aboard the Fraxinus who makes the decision making part. Parodied in Gravity Falls with Giffany, a perky AI from a Japanese dating sim which gained sentience and became a psychotic yandere towards anyone who plays her game.
Masques and Murder is a vicious Genre Deconstruction: Flirting with Papyrus during your battle with him unlocks an optional dating sidequest.
As Papyrus's never dated before, he consults a guidebook on what to do and ends up believing that you're madly in love with him even if you spend the entire date insulting him. Not only that, but his Large Ham personality leads to him treating the date as more like a competition to see who has the most "Dating Power". At the end of the date, he admits that he doesn't like you in that way and would prefer to just be friends.
The True Pacifist route includes a similar comedic "date" with Alphys at the local garbage dump. Being a bit Genre Savvy , she brings gifts intended to increase your Relationship Values with her, but they're all obviously intended for a different person, namely Undyne, who actually wrote the love letter Alphys mistakes you as the author of.
The date turns into more of a pep talk session that's then unceremoniously interrupted by Undyne. Monthly Girls' Nozaki-kun had a story where Mikoshiba convinced Nozaki to try a dating sim in order to try and understand girls better.