Answering a slightly broader question of "how does one level up at rationality", which a bias towards ways that include exposure to people more skilled than you:
I would expect that if casual levels on interaction with stronger rationalists could feasibly raise your own levels, that Berkeley rationalists would be significantly stronger than their pre-Berkeley selves, or than rationalists elsewhere.
I don't think that's the case, but I guess that can be an open question.
People joining one of the orgs DOES seem to level them up.
The big difference there is 40 hours a week of intensive work on accomplishing an outside goal.
But given that like: living with rationalists, in a community of rationalists, that often talk rationalist, doesn't seem to have much effect, it seems unlikely that weaker versions of the thing would.
(Single datapoint: I did most of my levelling up when I was running a rationality group that was giving frequent public facing classes. I did not level up from moving to Berkeley and immersing in the rationality community there.)
I don't know of specific 2-person exercises, in part because I think most of the benefits are from personal practice rather than interaction. But you should certainly ask for general feedback on what they think you can improve in your life, and talk through things with others when you are feeling confused - and people who are good at thinking clearly / rationally are valuable partners for doing that.
As mentioned in my previous post, I currently estimate that I am about as strong in applied rationality as the average CS undergrad. But I know Mark Xu, who has gone to CFAR, and is certainly stronger than me, enough to occasionally find interventions that can fix my problems. I don't want my friendship to become a formal mentorship, and the gains from taking advice or copying someone else's interventions into one's own life run out quickly. There's even the risk that I stop thinking for myself when my best judgment is on average more wrong than base rates + someone else's opinion.
Personal details aside, are there exercises/drills in applied rationality where one participant is much stronger than the other, but doesn't have CFAR instructor-level skills? I'm especially interested in examples that work in situations similar to mine, both for selfish reasons and because I suspect this situation is fairly common. Even more valuable would be a general framework.