Different people seem to have different strategies, which they use systematically across different parts of their lives, and that we recognize and talk about. For instance people vary on:
- Spontaneity
- Inclination toward explicit calculations
- Tendency to go meta
- Skepticism
- Optimism
- Tendency to look at the big picture vs. the details
- Expressed confidence
- Enacted patience
I don’t know of almost anyone experimenting with varying these axes, to see which setting is best for them, or even what different settings are like. Which seems like a natural thing to do in some sense, given the variation in starting positions and lack of consensus on which positions are best.
Possibly it is just very hard to change them, but my impression is that for at least some of them it is not hard to try, or to change them a bit for a short period, with some effort. (I have briefly tried making decisions faster and expressing more confidence.) And my guess is that that is enough to often be interesting. Also that if you effortfully force yourself to be more skeptical and it seems to go really well, you will find that it becomes appealing and thus easier to keep up and then get used to.
I also haven’t done this much, and it isn’t very clear to me why. Maybe it just doesn’t occur to people that much for some reason. (It also doesn’t occur to people to choose their value of time via experimentation I think, a related suggestion I like, I think from Tyler Cowen a long time ago.) So here, I suggest it. Fun date activity, maybe: randomly reselect one personality trait each, and both try to guess which one the other person is putting on.
Meteuphoric 
I’ve received surprising pushback (defesiveness?) on what I consider a fairly good heuristic, which is to use systematicity to decide on context and spontenaity once within that context. This could also be framed as open vs closed mode.
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I’ve tried this and it’s exhausting work. Your date suggestion reminds me of the historical “imitation game” (the inspiration for the Turing test IIRC.) Historically I think this was a pastime enjoyed by the elites – both men and women.
I have a heuristic that I’ve found fairly useful in thinking of ideas about how the future should maybe go. It’s to look at what the people who today are currently considered “the elites” do as leisure pastimes, since historically that has been a source of progress (the elites were the only with access to books -> printing press.)
What I see today is not encouraging. The people with the greatest temporal power currently seem to treat people’s lives as a game, and mainly play power games with each other.
My view is that if life is to be treated as a game, it must be fair and balanced. This means that equality of opportunity is an obviously correct moral principle, for example.
What I see is that due to Moloch (see Scott Alexander) this correlative heuristic approach (translate progress by essentially what is just envy of your neighbour in today’s globalised world) is no longer enough.
Good people must do what it takes to *make* the world a better place. In short, I fully agree with Scott when he says that we must kill Moloch. (as an aside, historically I came up with the idea independently. Being me, of course I tried to find a practical effective method that would actually work.)
You may perhaps read this with the tone and context of the movie The King’s Speech, in particular the speech part, which begins with the beginning of Beethoven’s 7th. That was about World War 2.
The task we have is more difficult. Therefore we must be better.