Winnie, a dating blogger who writes under the pen name Luckless, unexpectedly goes viral after publishing a post about a disastrous date with Holden, a sports agent. When her boss offers her a dedicated column, Winnie faces a dilemma: she must keep dating Holden to maintain her newfound success. As she navigates the fine line between professional obligation and genuine connection, Winnie begins to question her motives and her heart. Luckless in Love is a heartwarming romantic comedy about unexpected connections and staying true to oneself.