Although Charlie Harper was a wild womanizer, he had some significant relationships in the past. Charlie and Jill dated for some time, and broke up. Jill apparently broke up with Charlie, which apparently saddened him. However, Jill was important enough to Charlie that he was able to recall both him and the relationship they shared. Five years later, Charlie received an email from Jill, stating that he wanted to "see" him, and to meet him at a bar. Charlie decides to do so, as he enjoyed his time with Jill.