When Chelsea learns that one of the bar's customers, Tim Kornick (guest star NAT FAXON – Allen Gregory), is a marketing executive, she starts dating him to help get Olivia an interview at his firm. Much to Chelsea's dismay, however, Tim is intensely sentimental and cries at the drop of a hat. As Olivia's interview process slowly progresses, Chelsea must figure out how to shake off Tim
without insulting him or sabotaging Olivia's chances for her dream job.
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