The Boxman's Girlfriend is a song written by Jackson Kelley.
The song is another one about Jackson Kelley's bad luck with girls, except this one features the band mascot Boxman.
The video opens with Boxman (Jackson Kelley) writing a love poem, but he crumples it up and throws it in the trash. He then grabs a box of chocolates and walks out of his house. He sees his future girlfriend (Natalie Portman), and there is a flashback with Boxman failing to flirt with her. Then Boxman and some civilians dance in a field. Boxman goes to get the girl, but accidentally pees his pants, but the girl goes on a date with him anyway. They go to outback Steakhouse, where a waiter (Nick Stone) confronts Boxman, and Boxman storms out of the restaurant. Boxman and his girlfriend walk down a street and then they go to the beach, walking into the sunset.