Skyy Conrad is a single woman, approaching her 30s, who has decided to give online dating another chance after her first online experience failed. Never one to give up too easily, Skyy "meets" Bruce in a chat room and another online romance begins for the beautiful, wannabe writer who is also a full-time counselor at a correctional facility. Unlike Skyy, who is single with no kids, Bruce is divorced, with experience, who may have baggage that prevents the two from completely connecting on a few levels, especially physical. Along with the obstacles of trying to have a successful long-distance relationship with Bruce, Skyy also works hard at advertising a blossoming, promising online relationship to doubtful outsiders to online and long distance dating, such as her parents and friends, while questioning whether the relationship does actually have a chance of making it.

Dating My Boyfriend's Brother is an example of what can happen in a relationship that begins online, and what can happen when you match a determined, driven single woman ready for a man to put a "ring on it" with a divorced man who although is lonely and looking for companionship also has a weird way of showing how much he needs Skyy. Maybe it is indeed his fault that she begins to fall for his brother

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