Just like Jessie, Dad’s memories of Chicago no longer match the reality—Adam has been working out and is clearly no longer the scrawny child that Dad remembers. Jessie isn’t either, for that matter—now, she’s better able to think of others and how things feel for them, which is why she’s suddenly able to consider that this has been difficult for Dad. Then, when Dad reminds Jessie that Mom would be proud, it’s an important recognition on his part that Mom is still part of this family—her opinion, even if it comes from Dad’s mouth, still matters.