In Season 6, Lily (Ariane Rinehart) is introduced as the daughter of a bar owner who recently had to close down his business. When Otis goes in to see if he can buy any used equipment for Molly's, he meets Lily, and there is a spark immediately between the two. Otis is smitten with Lily, and the feeling is mutual. He goes from looking for some cheap equipment to buying the bar, and he convinces Hermann and Dawson to hop on board. Lily's family bar is now known as Molly's North, thanks to Otis.

Lily is also a tremendous support for Otis after his neck injury in Season 6, and sticks by him in the hospital and during his grueling physical therapy. This is Otis's second and last relationship on the show, but he definitely has one of the healthiest love lives out of any "Chicago Fire" character. We don't get to see Lily's reaction to losing Otis in the Season 8 opener, but we find out that she chose to close down Molly's North, as it was too much of a reminder of her fallen beau.