Part of the problem I believe is that I am attempting to do a bit of original story telling that hasn't been done before. Not only it is difficult for me because I do not have many examples to follow, but also odd for the player because the story arch does not follow typical story arch conventions.
Each of the four stories contains two objectives: an internal story objective, and an arch objective.
Story 1: Another Date
Internal Story Objective: Give players of Date Ariane a new dating experience with Ariane, introducing a linear visual novel format, while also better defining Ariane's personality. In Date Ariane, Ariane is likeable enough, but we never get to learn much about her. Now we learn she is a former cheerleader as well as a gymnast, that she likes to do daring things, both physical daring as well as naked daring things, that she has no desire for a defined relationship, that she gets brutally honest when she gets mad, etc.
External Story Arch Objective: On every date you go on with Ariane, a surprise lightning storm hits right around 11:00.
Story 2: A Man About Town
Internal Story Objective: A return to the chaotic Dating Sim style of the first game. This could also be called "Date Rachel", and the rules of the game are a bit less defined than the linear story 1. Earlier versions were even more complicated than it is now, but I had to tone it down a bit.
External Story Arch Objective: On every date you go on with Rachel, a surprise lightning storm NEVER hits around 11:00. Despite multiple play throughs, everyone keeps missing this, and thus the forest through the trees is never seen.
Story 3: Magic, Malice, and Mayhem
Internal Story Objective: Both Ariane and Rachel are very likeable and every ending with them seems to be at least pleasant. Show some girls that are not as likeable for opposite reasons, and have the player lose control and the dates end badly, because some dates do end badly. Lack of player control is illustrated by making the story more "comic book": different text style, not always first person, multi-pane images, floating onomatopoeia words representing sounds.
External Story Arch Objective: Is there a storm? Or isn't there? There is! At this point you should be asking yourself, what makes Rachel so special that rain never falls on her?
Note: The reason why there are only two linear stories, is because that is all it takes to meet these two objectives. By the way, there are 10 different endings to the Bonnie the Bartender story, but only two count. The Bonnie sex ending is different the first 9 times you play her story, all 9 endings are bad (but mostly funny). The fact that you can't control the outcome, and that the outcomes are completely contradictory, is designed to make the greater point that having sex with someone you barely know has potential consequences.
Story 4: Tower of Ion
Internal Story Objective: A sudden change of genre, less romantic comedy, more sci-fi mystery. Hence, the many Fringe references throughout the story. Not only a change in story genre, but in game genre too: This is an adventure game, with many puzzles to solve to reveal more information. Adventure games generally don't branch out to alternative endings the way visual novels do.
External Story Arch Objective: Solve the mystery as to why it never rains on Rachel. If Rachel never gets to the LAN party, she never goes to the lab to see that conditions are ideal for the storm making machine. It never gets turned on.
Historical side note: I believe that I am the first romance writer to end a romantic story where one person give another a math lecture, then makes them solve a 4 dimensional linear algebra problem for them.