Sometime prior to the start of the series, Myles and Sierra met and later went on to marry and have a daughter together, Josie. Due to Myles's career as a professional jazz player, he is often absent.
As Josie and the Pussycats would be performing in the 75th annual Variety Show, Myles had decided to come to town especially to see Josie perform. Sierra warned her daughter not to disappoint her father as he would somehow find a way to blame her.
During a dinner with their daughter Josie, Hermione Lodge, Fred Andrews his son Archie, Fred commented that Myles must be living his dream playing music professionally to which Myles agreed, but the real struggle for him was art versus commerce. With a pointed look, Sierra said that in order to be financially secure for the future, life couldn't always be about following your dreams. Later, Fred presented his bid to Sierra to develop the Twilight Drive-In's land and Sierra and her husband clashed once again when Myles called Fred a "dollar chasing gentrifier". Sierra defended Fred, stating he was a working man who lived in the real world, a subtle dig at her husband.
On the night of the Variety Show, Myles and Sierra sat in the audience as the Pussycats performed a cover of Donna Summer's "I Feel Love". Sierra watched proudly, however, Myles was unimpressed and displeased, so much so that he left in the middle of the performance much to Sierra's disappointment.