"The year I got a life long ban?" Harry wondered aloud, rolling his eyes. If he ever saw Dolores Umbridge on a dark street, he really thought he'd have no problem hexing the woman(if you could call her that. "Wait. You knocked yourself out with your own bat? Brilliant!" He exclaimed with a grin, laughing. "I mean, ouch? But I have to admit, the mental image there is pretty hilarious." He continued snickering for several minutes, amused by the image it created in his head.
"Oh no, I mean I think I'd go crazy if I weren't responsible for my own life, my own schedule." Harry answered, waving the idea away as if his hand were a broom and the idea were dust on the floor. "And I admit, I'm not great with authority figures telling me what to do. Even if it's one I hired." He snorted at the mention of love letters, rolling his eyes. "I don't get many love letters, not really."
Harry listened to Jack explain more about his other job and, in a moment of boldness, pointed out, "Secretary, huh? Well, maybe you're my type then." He was teasing, of course, but he couldn't keep the blush entirely off his face and his grin, while playful, held that edge of sheepishness, nervousness. He shrugged it away and finished his mocha, setting the empty cup aside so he wouldn't play with it.
"I thought the drawing you did of that lady was really good," He mentioned, surprised once he'd heard that Jack had never taken art classes or anything. "I mean, it was hilarious, but there was real talent there. Not that I know much about art, but I was impressed."