Hey, I need some guidance on how I would go about making a dating sim (for reasons I dare not disclose).
I'll start with the assumption you can find (or have found) the scripts and tilesets that fit your theme. So, I'll give some generic advice to begin with, at the least.
(I'm also assuming this project is of your own characters, not based in an established fandom; fan-shipping games benefit from having established characters, but have their own idiosyncracies from the fandom themselves; namely, that the prospective players will be more opinionated on the what and how of the characters dating.)
Many of the aspects of a "good" dating sim may presume you, the developer, are at least acquainted with other dating sims, and have played some to have the experience. Humans being what they are, I cannot say you'll really be doing anything "new" or not done before; maybe having a psychology textbook nearby may make for an interesting diversion if you have "writer's block" in the plotting, even if very little of that ever goes into a game -- it's a bit like how less than ten percent of an iceberg is often actually seen, yet failure to take into account the other ninety percent can be a "ship-killer", if you pardon that pun...
More than being worried about the scripts and tilesets, pay plenty of attention to the overall characters and their characterizations. Are the characters starting at zero relationship, or do they at least know each other in passing? Dating sims often tend toward the young, high-school-aged children; but it could be just as valid for a dating sim to be about adults in a working environment, or at a sequence of social gatherings, where the potential couple(s) cross paths.
Is it just one main character, with one target for the romance, or will you have multiple options for the success of the game? It may just be my own opinion, but while both may have their own difficulties, I'd tend to think the former could be more difficult than the latter. I've watched a dating sim let's play that felt like the game author got too wrapped up in that singular romance objective, that it didn't feel like a balanced game, like the player was being railroaded into the romance. I think that's why many galge and dating sims widen out to more than one romantic option -- less chance of suffering "tunnel vision" on the dating of just one character.
Each character will almost necessarily have some backstory, as well as a motivation, some reason they are the way they are. Conversations can help draw them out, but also the absence of responsiveness, or refusal to respond to a conversation, can also be used effectively, especially for the more reserved or standoffish of characters.
And then we have the timing of how quickly or slowly the relationship(s) can or will advance, in terms of game-time, but it may also have a part in how enduring the relationship may be. It depends upon how quick a game you want your potential players to experience; simple "get the girl" games can be played through in as quickly as less than a half hour, or conversely, the more enduring the intended relationship -- rather, should say "romance" in the traditional sense -- the longer it may take to play to a final conclusion. Is the objective merely getting the date itself, or of something more lasting, id-est, marriage?
We may also be concerned with "replayability", in that having more than one conversational branching, more than one way to accomplish the dating/romancing/relationshipping, with possible variations in the aforementioned and consequences based upon conversation responses.
If the dating sim is being made in an RPG Maker, does this mean less combat, or even none necessary? I'd be more tempted to play it, given that I'm kind of wanting to play something that is more of a "thinking man's game" rather than repetitive combat events.
Chances are, the whole of my response might seem a little too long, but I cannot help it -- once I get started writing, I just gotta keep at it, while I've got the response in mind.... I wish you well in your gaming experiences, and if I can offer any more opinions or experiences, at your request I will.
