Emily Sanders is a successful publisher of self-help books who has terrific instincts in every arena of her life but one—relationships. Determined now to make better choices, Emily employs a "Reasons Why Not" list-making system designed to serve as an internal warning on when it's time to cut bait and move on. Navigating a thriving career, a string of would-be boyfriends and an office rival means that Emily's plate is always pretty full.
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01. Why Not to Date a Twin
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Best friend Josh convinces Emily to meet Vincent, the handsome architect that Josh has talked about— and to her delight, Emily is impressed. But as their relationship develops, Emily learns that Vincent has an ever-present twin sister (Vinessa) and discovers there are reasons why not to date a twin.
02. Why Not to Date Your Gynecologist
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Emily begins dating her gynecologist in an attempt to prove to her peers that she doesn't just date immature guys—only to discover the reasons why things between her and the doctor would never work.
03. Why Not to Cheat on Your Best Friend
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After Emily decides that she and Reilly disagree too often, she searches elsewhere for a new best friend, only to find out that true friends are hard to come by.
04. Why Not to Invite Your Vacation Date Home
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Emily tries to continue a steamy vacation fling with an exotic lover back at home.
05. Why Not to Hire a Cute Male Assistant
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Emily is overwhelmed at work and decides to search for an assistant.