broken - does it really matter? Either he's not ready to date, which is his problem, or he's just a control freak, which is also his problem.
I don't think it's a case of 'trying to be kind' - and even if it is, then he probably has ishoos. Who would meet someone they don't think they're likely to want to date, and set obstacles for them in the hope they fail them, just because they're trying to be kind?
The point though, is no matter what, he's not right for you, not good enough for you, and possibly not good enough for anyone except some fantasy woman who likes eating Asda Chocolate Sponge on her pedestal, so disengage and move on to the next one who will be better for you, or at least more normal.
Don't overthink the failures, it is their problem, not yours.