Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.
New York concierge Doug Ireland wants to go into business for himself and refurbish a hotel on Roosevelt Island, N.Y., but he needs an investor. With a few weeks left before his option on the site runs out, Doug agrees to help wealthy Christian Hanover conceal his affair with salesgirl Andy Hart from his wife. Despite his own attraction to Andy, Doug tries to stay focused on getting Christian to invest $3 million in his project.
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