Jacob is brutally honest here. He appears to consider his ongoing virginity as a kind of failure. However, his state also reflects his honesty. He suspects there might be other "old […] male virgins" out there, but they're all pretending they've gotten some. Jacob has standards that he won't lower for anything, even the much-desired event of losing his virginity. He won't lie and he won't participate in mass prostitution. Good values to live by, we'd say.

The Dean has "ask[ed]" Jacob if he will "be okay," and Jacob understands "okay" to mean something like all right, or normal, or fine. To Jacob, "okay" doesn't mean "whether [he's] going to cry" or not. And yet, that's all the Dean wants to know. Clearly, this guy doesn't understand the pain that Jacob is in.

When Jacob's parents die, he experiences suffering and grief like never before in his life. The fact that his parents have been taken from him so swiftly and unexpectedly only makes it worse. In this moment, he realizes that, in just the short span of a day, everything has changed. On the other hand, this terrible accident means Jacob's parents will never have to suffer old age, be sent to a nursing home, or have their offspring abandon them.