So, the guy who doesn't perceive boundaries until it is far too late and a guy who freaks out at the merest hint that he's made a misstep. Jeph really, really should have thought a lot more about whether these guys were plausibly compatible before arbitrarily pairing them up.
True, however, they are also both open minded, willing to admit mistakes, willing to work on themselves, and very much working on growing and being a better themselves.
They are very much alike in that journey, which can create a feeling of kinship.
If they establish trust and practice open communication - which they have already been working on - I do see this working actually.
Upside, they will both get quite a bit of practice on working on their weak spots. They definitely would run into some boulders, especially in the beginning.
But in my experience, even if you are relatively bad at reading people, you can become quite attuned to your partner, and pick up their signals way sooner.
And in reverse, even if you are bad at sharing things, the level of trust you develop with your partner makes that it's much easier with them to share your boundaries.
I'm speaking somewhat from experience here, I can be a bit obtuse at moments, my partner doesn't open up quickly.
But by being supportive of him speaking up, always listening when he does, and occasionally checking in if everything is okay, that is totally compensated. I mean, I can really really work.