This episode was the fourth one of the series directed by Kyra Sedgwick's husband, Kevin Bacon, and their daughter Sosie Bacon played Brenda Leigh's niece Charlene (Charlie). The other episodes directed by Kevin Bacon are Serving the King: Part 2 (2006), Blindsided (2007) and Sudden Death (2008).
Producer James Duff was so impressed with the performance of Kyra Sedgwick's daughter Sosie Bacon in "Loverboy" that he wanted her in the show, but Sedgwick opposed the idea, insistent that her daughter would not be getting involved with acting. Duff was eventually able to get Sedgwick to agree to Sosie having a brief role, provided it did not interfere with her education. Sosie portrayed Brenda's niece Charlie for four episodes. This led to what Sedgwick said was one of the hardest scenes for her on the show: Brenda tells Charlie that she must go home, and Charlie responding: "Do you not want me here?"
The final episode of The Closer that Sosie Bacon appeared in.