when does jess and nick start dating

She goes on a hiking trip to Mount Shasta , and when she returns she accepts his marriage proposal in the season 4 finale "Clean Break". On the way home Jess shows the guys Candy Cane Lane. Jess then gets a text from the delivery man she'd seen the day before, which overwhelms her because she's never juggled two men before. She tells the guys that she isn't wearing underwear, which Nick says makes two of them. She says he's been waiting all week for her to cry. She tells him that she's here for him. Nicks tells her he's sorry, but Jess says he's just 'getting some skank on it,' which obviously his boss takes offense to.

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