Ever since, nicely said, dropping out of college, he had more free time on his hands. More time to do what he felt like doing. You were homeschooled, but that didn't mean the educational stress was any less than if you attended an actual college, meaning you also had tests and exams to take.
You were working quite a lot, not wanting to mess up your own future by not studying, especially not after hearing what happened to him, which had you deeply worried. But as you had mentioned feeling a bit unwell in your last letter to him, he was equally as worried about you.
Having gotten sick from all the stress, you were tied to your bed, barely able to stay awake enough to get anything done. And even if he wasn't seeming like the most worrying and caring person, he did. More through words than through actions, but you know he did.
So as you were resting you heard the door to your room open, looking over slightly to see him standing in the doorway
"So you are quite sick, huh.."