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When Simon is nominated for the prestigious Impact Award for Advertiser of the Year, Sydney is surprised to find that her high school crush is in direct competition for the award against her father.
When a worldly client, Helena, comes to town, Sydney, Zach and Simon each compete for her attention, but when things turn to a sexual nature, they realize they may know too much about each other.
An infatuated ex-co-worker of Sydney's writes a stalker-ish song about her. Meanwhile, Simon struggles to pitch the Australian Tourism Board, the location of his final bender.