This charming feature-length romantic comedy stars Cristin Milioti (How I Met Your Mother) as 21-year-old Sammy Smalls, a young woman with big self-esteem issues. Sammy has spent her entire life hiding behind frumpy clothes, a slight limp and a dead-end job at a supermarket. But one day she meets Eugene, a musician she develops a huge crush on. As their friendship promises to grow into something more, Eugene picks up on Sammy’s lack of experience and refuses to take things any further. In an effort to win the heart, and body, of the man she loves, Sammy embarks on a quest for sexual advice and experience, taking it from wherever she can get it… except from Eugene.