There was a Cave Story dating sim in the works a couple years ago, it was a yaoi dating sim, which is a better idea, tbh.
Cave Story Tribute Site Forums
Serri
EnlightenedOne
The existence of a Jenka Dating Simulator has been rumored for eons now.
Garp
Jenka Dating Simulator...is this the yaoi one or...not yaoi one ?
Serri
Yaoi means gay, and Jenka is a bad meme. No one wants to fuck old women