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Flirting with Papyrus during your battle with him unlocks an optional dating sidequest.
Date A Live plays this straight with the twist that the protagonist doesn't make the decision making part. Being a bit Genre Savvyshe 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. It ends up failing in an epic fashion. The eighth episode of the television anime has the cast stuck in a cursed dating simand they will only escape once Mahiro declares his love for one of them.
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. He is reluctant to do soso it works out as an inversion as above.
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. Rather, it's his sister and the Ratatoskr crew aboard the Fraxinus who makes the decision making part.
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". It's an Inverted Dating Simthe character has SAN among the character's statswhich measure your resistance to the Yanderes who are after you.
The fourth episode of the Haiyoru! A Yuria Shiki omake features the Yuria Shiki eroge.
However, the only character with whom Tomoda has any meaningful interaction is the main character himself, which results in the doujin unintentionally becoming Boys Love.
Peace Walkerwhere you can go to the beach with either Paz or Kaz.
It's mostly just them saying "Duh", occasionally pausing to talk about how awesome Strong Bad is. Monthly Girls' Nozaki-kun had a story where Mikoshiba convinced Nozaki to try a dating sim in order to try and understand girls better. At the end of the date, he admits that he doesn't like you in that way and would prefer to just be friends.
2. The Sims
This is the main point of Experimental Comic Kotone. 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.
There's two 'dates' in Metal Gear Solid: 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.