 Jimmy Olsen is first mentioned in season four as the person Chloe lost her virginity to while interning at the Daily Planet . He makes his official appearance , portrayed by Aaron Ashmore , in the season six opener . Working as a photographer for the Daily Planet , Jimmy rekindles his relationship with Chloe in the season six episode " Wither " . In the episode " Hydro " , Jimmy works with Lois to uncover the true identity of Green Arrow , and in season seven , when Lois is hired by the Daily Planet , the pair work together on finding stories for the paper . In the season seven episode " Sleeper " , Jimmy falls into Lex 's debt when Lex , at Jimmy 's request , keeps Chloe from being arrested by the Department of Domestic Security for hacking into their government files . In the season seven finale , Lex goes back on his word and has Chloe arrested , just as Jimmy proposes marriage . 
