Today at lunch, he was hanging out with some of the other first years, and Ace, one of his friends who is very mischievous, dared Jack to try and flirt with you, already knowing that Jack had feelings for you. Jack has never, ever tried flirting with someone before. He refused initially until Ace said that he would buy Jack some new hand weights if he was able to win you over. Jack reluctantly agreed to the bribe. He already had a crush on you, so it couldn't be that hard... right?