Allison Weiss began playing music as a teenager in her hometown of Flowery Branch, Georgia. Inspired by the emotional tumult of young relationships, she began writing songs, adopting a D.I.Y. ethic that would stay with her throughout her career. Weiss released her first EP, An Eight-Song Tribute to Feeling Bad and Feeling Better, in 2007 while attending the University of Georgia in Athens, Georgia. She followed it up with a full-length concert album, Live at Sidewalk NYC, a year later.
In late 2009, Weiss turned to the newly launched Kickstarter crowd-funding platform to try raising the money for her first studio LP, ...Was Right All Along. Her campaign allowed her to reach her funding goal within the first day and triple it just days later. The Kickstarter success led to some high-exposure press, with The New York Times and Wired magazine essentially labeling her as a sort of poster child for the new era of Internet promotion. Weiss capitalized on the attention with countless tours, interviews, and a panelist slot at the industry's SXSW conference in Austin alongside Kickstarter founder Yancey Strickler. She busied herself over the next two years by focusing on her songwriting and touring.
In 2011, Weiss recorded her second studio album, Say What You Mean, as well as a companion acoustic record called Sideways Sessions in Brooklyn, New York. Both albums were released on No Sleep Records in 2013. The label released an EP from Weiss titled Remember When the following year.
In May 2015, Weiss signed with SideOneDummy Records and announced plans to release a third studio album later that year. New Love was released on October 2, 2015 and produced by Forrest Kline of electro-pop band Hellogoodbye and Bradley Hale of indie rock band Now, Now.