In 2005, Swanberg directed his first feature film, Kissing on the Mouth, for a modest budget. He followed it with LOL (2006), which marked Swanberg's first time working with Actress Greta Gerwig. Gerwig and Swanberg collaborated on the director's next two features: Hannah Takes the Stairs (2007), which also starred filmmakers Andrew Bujalski, Ry Russo-Young, and Mark Duplass and marked Swanberg's first collaboration with Animator and actor Kent Osborne; and Nights and Weekends (2008), on which Gerwig shared a directing credit. Swanberg's next feature, Alexander the Last, was produced by Noah Baumbach, who would later cast Gerwig opposite Ben Stiller in his 2010 film Greenberg.