Jake struggles with a book report assignment by continuing to misplace the book, making Charlie and Alan revisit the bookstore. Charlie goes to the self-help section to figure out why all his relationships continue to fail, when he meets a woman named Angie (Susan Blakely). When they start dating, he struggles with the fact that she's much older than he is, but he continues to date her anyway, simply because Angie would make a great replacement mom. Alan teases Charlie about the age difference. When Alan finally meets Angie, he's instantly enamored and he starts having feelings for her. They also meet Angie's son, Mike, who's engaged and happens to be 32 years old.