Jane and Oliver first met in a fund raising gala at the Aebly Museum of Art held by Oliver when a tattoo sends the team after an assassin. Oliver approaches Jane moments after they both looked at each other during Oliver’s brief welcome to the gala. After being briefed by Roman on the Lake Aurora disaster, Jane asks Oliver about the same incident to check if her brother’s story was true. Interested on Jane and her enthusiasm on clean water issues, he hands her his card before she leaves.
Jane calls Oliver from the first time after meeting at the gala and laves a message in his voicemail asking him out for a drink.
Jane is surprised by Patterson texting Oliver, oblivious of his interest on her and to his invitation to go out; after an agitated day at the FBI, Jane is taken by Oliver to his favorite fast food spot in New York. Worried and interested on Jane’s nose injury, bruises and tattoos, Oliver tries to get to know some personal aspects of Jane’s life by sharing some of his personal information after she didn’t answer his questions. Realizing that her life and involvement with the FBI was too complicated and confidential, Jane leaves the place after mirroring Remi’s words from her latest dream: “this doesn’t belong to me”.
Jane and Oliver spend an afternoon at an amusement park. Jane apologizes about leaving without an explanation on their last date and admits to be willing to make their friendship/relationship work. They also kiss for the first time.
Weller asks Jane about her date and suggests her to be careful with the people she lets into her life after Borden tricked everyone, especially Patterson, by being a double agent working for Sandstorm, a moment later Oliver texts Jane about their date for that night. Once the case is done, Jane asks Zapata to do a background check on Oliver where they discover that he changed his name a couple of years ago.
Oliver arrives to Jane’s home after doing some groceries to cook dinner but before they could get started, she asks if he changed his name; Oliver is mad and confused for Jane’s invasion to his privacy, alluding to her unwillingness of sharing her personal information with him and then he leaves her place.