Leonard nodded. "Having a purpose is useful for keeping one motivated. It's good you have your family here, but a job would give you somewhere to be everyday." Leonard loved spending time with Sara, but he also knew that you needed more in your life than loved ones. They were a great supporting force, but having a job certainly provided motivation. Even if it was job Leonard never saw coming. Kind of like being potential hero.
"I kind of figured, but yeah, you won't know until you ask Sara." Leonard wasn't opposed to the idea, but it was Sara's call in the end. She owned the club and if she'd rather avoid that awkwardness, Leonard could not blame her. While he might find it amusing, Sara might not feel the same.
Leonard chuckled. "I'm positive there are. As I said, it would be a perfect fit." And it wasn't as if Oliver was the only one with a police record sitting at that table.