An investment banker loses everything and must discover what's important in life.

Ryan is a womanizing stockbroker whose unethical business practices cost him his job and his trader's license. Unable to find another job, he is forced to move in with his equally self-involved (and completely oblivious) girlfriend, Cindy, an insensitive advice columnist on the cusp of losing her own job due to her poor advice and slow work habits. Finding that the truth behind his moving in has nothing to do with romance, Cindy runs off with another man. Ryan decides to stay in the apartment and earn a living by doing Cindy's job. Ryan establishes himself with Cindy's editor, Page, as Cindy's go-fer, collecting Cindy's paychecks and mail and delivering "her" columns. Initially as hopelessly inept as Cindy in giving advice, he nearly gets the column canceled. However, he rapidly grows into the job and the combination of forced introspection, research and the growing knowledge that he is touching other people's lives transforms him. The column becomes an amazing success. Ryan finds his initially superficial attraction to Page growing into love, but he cannot reveal his feelings while he is a deceptive fraud. Meanwhile, Cindy becomes aware of "her" growing fame, and returns to cash in, at the same time that the owner of a rival newspaper chain attempts to force Page to sell "Cindy's" column to him.—Anonymous

Ryan and Lucy deserve each other. Lucy lives in a small apartment while earning enough to get by writing an advice column for a small newspaper failing despite the new owner/editor Page's best efforts. Page is so broke she can't buy out Lucy's contract despite disliking Lucy's column. Lucy would gladly quit if Ryan married her and maintained her in the style she feels entitled to, but he won't even let her move into his luxury apartment. So, Lucy is upset when Ryan moves into HER place. Ryan has lost all his money investing in a stock on a tip from a CEO he was cuckolding. To add insult to injury, the SEC suspends his broker's license, his boss fires him, and no one else will hire him. Ryan now spends his time drinking beer in his bathrobe while watching Lucy's TV and won't even leave the apartment to take her out. One morning Lucy packs her bags to fly to Brazil to live with a diamond mine owner. Her parting words are "the rent is due." When Lucy's next column doesn't arrive, Page calls the apartment to warn Lucy no column breaches the contract which means no more checks. Ryan sees an alternative to living on the street - how hard can it be to write Lucy's column and cash the checks while making excuses to Page for why Lucy isn't coming to the paper herself? Very. Page hates "Lucy's" next column and Ryan hates lying to the woman he is falling in love with. Can he figure out how to give good advice? Can he get Page to forget he is Lucy's boyfriend and fall in love with him? Can he really get away with being "Lucy"?—CComly