I like the 5 day repeatable dating sim framing, I don't think I've seen something like it before. The interaction history is also a really interesting approach to relations. Cruise upgrades are a fun way to shake things up between loops. Perhaps the speed at which the upgrades are offered can be increased, or the clothing upgrades can be given as a free bonus?
The randomized characters work well with the repeating nature of the game, but the flavor text feels too specific at times for something you will see repeatedly. Maybe the stories can be tied to the first characters who say them, and repeated occurrences will give you something shorter and generic? Reducing the amount of people on the ship could also help to make them feel more unique and easier to remember.
The area flavor text is a neat way to add some personality to the characters, but perhaps it can be relocated to a place where the player won't need to click through it. Maybe to a small area of the screen or an on-hover description? It will also give players another chance to see the name of the person it describes.
It's hard to reinvent the dating sim formula, but the setup you came up with is quite clever and new! Nice work!