Jack Cody, one of the most sexist sports columnists in NY, gets fired from his job at the Dispatch for a 21 million dollar litigation lawsuit. Without anywhere to go (since he'd been banished from several other papers), Jack decides to take one of his best friend Ronnie's idea seriously: take over the ""Ask Harriet"" column at the Dispatch. The past Harriet (there were a bunch of them – like Lassie) died and the paper was looking for a replacement. This way, not only would he get his revenge against Melissa Peters (his boss), but also a really easy and nice paying job. The only problem is Jack (or Sylvia, the new alias created by Ronnie for Jack) has to meet with Melissa. Jack is forced to put on a dress and high heels and try to fool Melissa – which he does! Melissa is so impressed with the ""new"" Harriet that she decides to introduce her to the press and make Sylvia Coco the most high profile Harriet to date. Jack does fine, but he soon gets a taste of his own medicine when a date of hi
When Jack learns that Old Man Russell, the newspaper's owner, is coming, he tries to get back his job as Jack, but the Old Man finds ""Sylvia"" more to his letching, er, liking.
""Sylvia"" announces she's leaving the newspaper to live among the apes in Rwanda, but the scheme to get Jack rehired is jeopardized when the bidding war with Old Man Russell makes him go bananas.
""Sylvia"" goes to pick up her first paycheck, only to find that she can't get it until she gets a physical examination - from a gynecologist.
When Old Man Russell sponsors a charity celebrity auction, Sylvia has to fend off Trey and Mr. Russell, while Ron and Melissa discover the awkwardness of being ""close to you.""
Jack is forced to attend Sylvia's surprise party.
A sexual harassment seminar gives Sylvia an idea to get Jack re-hired.
Jack masquerades as Sylvia in hopes of getting a date with a jilted co-worker.
Jack's ex is back and he tries to hide all the goodies he's been buying with Sylvia's paycheck (because to Valerie he's still unemployed). They start fighting about her boyfriend and end up sleeping together. The next morning, Jack tries to resume their relationship (in order to save the alimony money), but Valerie finds one of Sylvia's dresses and threats to end it. Jack arranges for her to meet with Sylvia – a very risky move – and Valerie buys it! Unfortunately, the fire alarm goes off at the office, preventing Jack to go back to being a man. When he comes home, Valerie is waiting for him with a very sexy negligee. She certainly wasn't expecting to see Sylvia there, so Jack reveals her the truth in order to spare their relationship.