Ross, twenty-three, has just broken up with his true love, Lora, in a foolish attempt to demonstrate how miserable life would be without him, only to find out she's already moved on and into the arms of the alcoholic younger brother of a famous network TV actor. But the universe isn't done piling on. After getting back on the horse with a woman he doesn't quite care for, Ross believes he's incurred a karmic punishment when his parents die in a fiery helicopter crash while on vacation in Turks & Caicos, leaving him to care for his adolescent sister, Emily, and the millions of dollars they've each inherited. Newly orphaned and a single parent, Ross sets out to win back his ex, adopting progressively intricate schemes in an attempt to make himself more able, more competent, more adult, and, more importantly, to make Lora realize this.

As he struggles to entice his ex, Ross is forced to reckon with his loss and possibly regain his values in a world seemingly devoid of them. Let Me Try Again is a critique of today's culture at large, touching on grief, loss, and narcissistic self-improvement.