It was released to American country radio on September 25, 2017 as the album's second and final single, and it features lead vocals from Scott.

[10] Matt Bjorke of Roughstock called "Heart Break" "perhaps the best potential follow-up to "You Look Good" as a radio moment," and praised the song's message of independence.

[11] Annie Reuter of Sounds Like Nashville wrote that the track is "one of the more memorable songs" on the album for its distinct storytelling.

[12] Cillea Houghton of Taste of Country wrote that the song "celebrates singledom with a chill vibe and a perky, pop-driven sound," and that it sets the tone for the rest of the album, which she reviewed favorably.

As the song reaches its first chorus, the woman is seen walking around the center of San Juan in sunglasses and a flowing crop top and her purse over her shoulder.

She returns home and sits down on her balcony with a glass of wine in hand as Lady A finish the song at the empty bar and make a toast.

After performing "Heart Break" on the ACM Awards, it sold 12,000 copies, a boost of 1,102% over the previous week.