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Standout Track: No. 1, “Roatan,” the dreamy, doo-wop-infused waltz that kicks off the band’s sophomore album, Conventions. Formerly a folksy duo, Ugly Purple Sweater flaunts its expanded five-piece lineup with the tune’s lush, poppy atmospheres, and frontman Sam McCormally spins a yarn about seaside temptation and “a girl in the white” who “likes how [he] whistle[s].” But, right at the fateful moment, he retreats: “God knows that I, I would never/There’s too many ways to be alone.”

Musical Motivation: Inspired by a vacation to the titular Caribbean island (“it’s sort of a schmancy, scuba-diving site”), McCormally says the song is about “not cheating on your girlfriend while visiting a foreign country.” Rather, “Roatan” is a slightly fictionalized account of a night spent hanging out with a new female friend on the island, and—after her feelings for him became apparent—the awkwardness he felt coming clean about his girlfriend back home. He didn’t do anything wrong, but McCormally still says he felt “unbelievably terrible” afterwards. The resulting “Roatan” is about “any of those anxious situations where you feel like you’re cheating on someone even though you’re not.”

Couples Therapy: How does his girlfriend feel about the song? “Well, she’s in the band, so she’s supportive of it.” McCormally says that writing “Roatan” helped him and Ugly Purple Sweater co-founder Rachel Lord move past a tiny hiccup in their relationship. “At the time that this happened, it was sort of upsetting, but codifying it in a song created the definitive version of the story for us. It helped us move on.” No kidding: They got engaged late last year.

Ugly Purple Sweater plays the Velvet Lounge on April 13.