"How Not To" is a song recorded by American country music duo Dan + Shay for their second studio album, Obsessed (2016). Written by Adam Hambrick, Paul DiGiovanni, and Kevin Bard, the song is one of only two tracks on the album not co-written by Dan and Shay. A mid-tempo country ballad, the song is about the struggle to move on from a breakup, only for those emotions about the former lover to come back. It was released to country radio September 26, 2016 through Warner Bros. Nashville as the album's second single. The song received positive reviews from critics, who generally praised the duo's vocal performances. "How Not To" gave the duo their third consecutive number-one hit on the Billboard Country Airplay chart. It also peaked at numbers 7 and 57 on both the Hot Country Songs and Hot 100 charts respectively. The song was certified Gold by the Recording Industry Association of America (RIAA), and has sold 158,000 copies as of July 2017. It also charted in Canada, reaching number 25 on the Canada Country chart. Two music videos were made for the song: an "instant grat" where a couple performs an interpretive dance that symbolizes the story from the track, and an official one where actors Katie Stevens and Pierson Fodé portray recovering alcoholics falling in love with each other.