The 2010s File Feature
How Not To
How Not To — Dan + Shay (2017) "How Not To" is a single released by country duo Dan + Shay in the summer of 2017, marking one of the pivotal moments in the g…
01 The Story
How Not To — Dan + Shay (2017)
"How Not To" is a single released by country duo Dan + Shay in the summer of 2017, marking one of the pivotal moments in the group's commercial development. The song was released on Warner Bros. Nashville and represented a continued evolution of the duo's sound toward a polished, pop-leaning country aesthetic that would eventually make them one of the dominant acts in mainstream country music. For a duo that had been steadily building momentum since their debut in 2013, "How Not To" served as an important chapter in a career arc leading toward their enormous later success.
Dan Smyers and Shay Mooney, the two members of the duo, had established themselves through a series of charting singles and well-received albums that demonstrated their knack for clean melodic construction and harmonically sophisticated vocal arrangements. Smyers, who handles much of the production and musical architecture of the duo's work, brought his background in music production and songwriting to bear on "How Not To," while Mooney's expressive tenor provided the emotional center around which the production was built. The chemistry between the two, evident from their earliest recordings, had by 2017 matured into something more assured and commercially confident.
The production on "How Not To" sits comfortably within the crossover country-pop space that acts like the duo had helped define during the mid-2010s. The song was co-written by Dan Smyers along with collaborators who worked within the Nashville creative ecosystem, producing a track that could comfortably occupy both country and pop radio formats. This dual-format appeal would become increasingly central to the duo's commercial strategy in subsequent years, as they found ways to reach audiences that did not identify primarily as country music listeners while retaining credibility at the format that had launched their careers.
The song's subject matter, exploring the emotional aftermath of a failed relationship and the difficulty of properly ending romantic attachment, fit squarely within the genre's established thematic vocabulary while being executed with enough melodic sophistication to feel fresh rather than formulaic. The duo's ability to make familiar emotional territory feel personal and immediate has been one of their enduring strengths, and "How Not To" demonstrated that capacity at a stage in their career when they were still establishing the commercial footprint they now occupy.
"How Not To" charted on the Billboard Country Airplay chart, continuing the duo's pattern of consistent radio presence during this period. The song's radio performance helped sustain the duo's visibility between major album campaigns and kept their name active in the format playlisting that drives country music discovery. Country radio's role as a tastemaker and career builder remained significant during 2017, and the duo's consistent performance within that ecosystem was evidence of their careful management of industry relationships alongside their artistic development.
The track appeared during a period of considerable creativity and commercial momentum for Dan + Shay. Their album Obsessed had been released in 2016 and performed well, setting the stage for the more ambitious work that would follow. "How Not To" and the singles surrounding it represented a transitional phase, as the duo was simultaneously consolidating the audience they had built and experimenting with the sonic directions that would eventually produce "Tequila," their breakthrough crossover hit, and the self-titled album that made them country superstars.
The music video for "How Not To" received rotation on country music television platforms and contributed to the promotional push that supported the song's radio campaign. The visual presentation was consistent with the clean, handsome aesthetic that the duo had developed, presenting both members as relatably attractive young men capable of conveying genuine emotional vulnerability through performance rather than production tricks.
Critical response to the song was positive within country music press, with reviewers noting the duo's continued improvement as songwriters and producers. The track was cited as evidence that Dan + Shay were developing a more distinctive voice rather than simply following the contours of whatever was working at radio in a given season. This assessment would prove accurate, as the duo went on to win Grammy Awards and achieve a level of commercial success that confirmed the trajectory visible in songs like "How Not To."
In retrospect, the song occupies an interesting place in Dan + Shay's discography as a document of an act in the process of becoming something larger than they had been, with all the energy and ambition that such a moment implies. Fans who have followed the duo from their earliest recordings tend to cite this period as when the pieces that would produce their breakthrough were visibly coming together.
02 Song Meaning
What "How Not To" Means: Romantic Failure and the Grammar of Heartbreak in Dan + Shay's Work
"How Not To" explores a specific and underrepresented emotional experience: the state of knowing intellectually that a relationship is over while being unable to enact that knowledge in behavior. The narrator describes a situation in which all the practical markers of a breakup are in place, but the emotional reality has not caught up with the logical conclusion. This gap between knowing and feeling is one of the most honest things a heartbreak song can address, and Dan + Shay approach it with a clarity and concision that gives the track its emotional usefulness to listeners who recognize the experience.
The song's thematic framework is built around incompetence at ending things, a condition the narrator identifies in himself without self-pity or self-congratulation. The title itself announces this framework as the central concern, and the song's lyrical development unpacks the specific ways in which this incompetence manifests, whether through continued contact, persistent attention to reminders of the relationship, or the inability to redirect emotional investment toward anything else. This catalogue of failure is rendered with enough specificity to feel personal while remaining general enough to be widely applicable.
Dan + Shay's approach to romantic failure consistently emphasizes emotional transparency over protective irony, a choice that has defined their appeal to a wide audience. Many listeners, particularly those who came of age in the irony-saturated media environment of the 2010s, find emotional directness from male performers refreshing rather than naive. "How Not To" participates in a broader shift in country and pop music during this period toward what some critics described as a new sincerity, in which performers demonstrated vulnerability as a form of strength rather than weakness.
The dual vocal arrangement that defines Dan + Shay's sound adds a particular layer of meaning to the song's subject matter. Two voices singing together about the experience of failed separation creates a subtle tension between the communal nature of the performance and the isolating experience being described. The harmony, which suggests togetherness and mutual understanding, frames content about disconnection and loss in a way that creates productive emotional complexity. The listener experiences togetherness and isolation simultaneously, which mirrors the experience of grief for a relationship that once provided exactly that sense of two-in-one closeness.
For Shay Mooney specifically, "How Not To" represents an opportunity to demonstrate his capacity for nuanced emotional expression within a framework that required more restraint than some of the more dramatic material in the duo's catalog. His vocal performance is notable for its control, the way he conveys feeling without pushing into melodrama, suggesting that the emotional experience being described is real and ongoing rather than processed and resolved. This quality of emotional immediacy in performance is one of the most valuable skills a country vocalist can possess, and it is evident throughout this recording.
The song's structure serves its meaning directly, with a verse-chorus architecture that repeatedly cycles through the experience of trying and failing to separate, reinforcing through form what the lyrics describe in content. Each return to the chorus is a re-enactment of the central dynamic, the attempt to articulate the pattern and the failure to escape it. This structural mirroring of content is more sophisticated than it might initially appear, suggesting a level of songcraft that would pay dividends in the duo's later, more ambitious work.
In the context of Dan + Shay's catalog, "How Not To" is best understood as part of a sustained exploration of romantic experience that defines their artistic identity. Unlike artists who deploy romantic themes as background for other concerns, Dan + Shay treat romantic emotion as their primary subject matter, approaching it with a seriousness that demands comparable seriousness from their audience. "How Not To" represents one of the more honest and careful treatments of relationship failure in their discography, a song that earns its emotional impact through precision rather than volume.
→ More from the 2010s File
View all 2010s hits →
Keep digging