i've been doing it for almost four years now, and it's amazing to see how wrong and how frequently wrong your preconceptions and expectations can be.
you don't need an app to do that though. a spreadsheet is perfect for that purpose (and telling Google Assistant to 'flip a coin' or 'give me a random number between 1 and 20') and gives unlimited flexibility and less reliance on developer to implement features you want. not a lot of people appreciate this, but sometimes trying to accomplish a task with the general-purpose tools you have at hand can lead you to discover solutions so good it is in fact superior to any dedicated tool.
But in your case you still have to pre-select a range of options right? How do you avoid missing the 'unknown unknowns' that a separate service might help provide?
take restaurant choice for example. yes there's a range of options, but some of the fields instead of saying "go to restaurant A" say something like: "let google pick a random number X between 1 and 50. google "restaurant near Penn Station" and go to the Xth result."
multiple times this procedure led me to dine at fine-dining establishments that i would never consider going into with the clothes i have on (the experience almost always ended up better than i imagined). a nice thing about randomizing is that you become psychologically dissociated from your actions. when things go bad you don't blame yourself and take that to reflect on yourself ("well, i was just following orders"). when things go well you just feel thankful.
you don't need an app to do that though. a spreadsheet is perfect for that purpose (and telling Google Assistant to 'flip a coin' or 'give me a random number between 1 and 20') and gives unlimited flexibility and less reliance on developer to implement features you want. not a lot of people appreciate this, but sometimes trying to accomplish a task with the general-purpose tools you have at hand can lead you to discover solutions so good it is in fact superior to any dedicated tool.