The trick to 'your choices matter' stories is that most of the time the story options diverge, but then return to the same point before the next big choice, so you don't have infinitely spreading branches to deal with.
It's also okay to give different levels of weight to choices. The more the player has to do to unlock that choice, the more impact that choice has on the following events. For example, you just went into the trial and beat it in an expected way with minimal prep? Cool, you get slight variance in dialogue based on how you did it. If there was an option that required more prep and could be easily missed? If the player put in that extra work, they deserve a more unique event / dialogue afterwards as a reward.
You can also look at how much a player has done. So for dates for example. You already have a date? You probably interacted with that date a good amount already, so you don't need a super in depth scene, and some basic variance in dialogue is fine.
You don't have a date? Means you like had less interaction / pay off from your interactions, so let's try to give you something to be invested / excited about. Maybe a potential date comes up to you after the trial, and who it is depends on how you beat the trial. Maybe a character that previously wasn't available as a date is impressed by your performance and comes up to you since you don't have a date, giving you a reward for sticking with the story despite not getting a date yet.
Obviously it's fine for there to be situations where every choice has big variance, or choices where the variance is always minimal, but I think variance in the weight of choices gives replayability without overworking you.
There's also just the possibility of waiting for choices to pay off. Like you make a choice, you don't immediately see anything come from it, but then in 2-3 updates suddenly something you did in the past gets referenced and that also makes it feel like your choices matter and that the world remembers what you're doing, even if it's only a few choices that the game actually remembers.