"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. It was released to country radio September 26, 2016 through Warner Bros. Nashville as the album's second single.

"How Not To" is a country music song written by Adam Hambrick, Paul DiGiovanni, and Kevin Bard and produced by Dan Smyers and Scott Hendricks. It is a midtempo ballad with melodic verses that build into a bigger chorus and is instrumented by piano and electric guitar. The song's hook is accentuated by a "melodic lift." The lyrics describe the difficulty of moving on after a breakup when the narrator's emotions keep drawing him back to that person.

In a review of Obsessed, Annie Reuter of Sounds Like Nashville wrote that "their ability to translate the emotion in a song they didn’t write like 'How Not To' is the sign of a true artist," and described the song as "poignant." The staff of country music blog Taste of Country praised the vocal performances on the song and called it a likely hit. "Dan + Shay aren't really breaking any new musical ground here," they write, "but wow, do they sound sweet not doing it."

"How Not To" was the most-added new single on country radio the week of its impact. The song debuted at number 59 on the Billboard Country Airplay chart dated October 15, 2016. It reached a peak position of 6 on the chart dated June 3, 2017. "How Not To" debuted at number 50 on the Hot Country Songs chart dated October 29, 2016. It reached a peak of 11 on the chart dated June 3, 2017. The song has sold 109,000 copies in the US as of May 2017.

An "instant grat" video accompanying the song was uploaded to the duo's official YouTube channel on May 20, 2016 in promotion of the song's then-upcoming parent album. It features a couple engaged in an interpretive dance that is meant to symbolize the break-up story told in the lyrics.

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