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Kate tells Charlie that a 32-year old virgin patient of hers is looking for a "first experience" that won't be traumatizing, and Kate thinks a "close friend" might be the ideal sex surrogate. Charlie assumes it's him, approaches the woman, and they sleep together. But in the meantime Kate decided to go with a professional sex surrogate, and later tells Charlie that he was not the "friend" she had in mind. Meanwhile, Sam and Canvas get temporary tattoos to test Jen, but Jen thinks they are real and is sure that Charlie will freak out. So Jen gets a real tattoo in the same place as Sam's, so she can tell Charlie it was a mother-daughter thing.