Holy Moly (2011)

After suffering a devastating breakup, Sammy accepts the services of a 'life-enhancement' coach named Tabitha. Tabitha instructs Sammy in the skills every real man should have: shooting a gun, driving a fast car, and being decisive. Sammy attempts to use his new skills to woo back his ex through a series of voicemails, while Tabitha harbors other intentions for her protege

Unfortunately the movie Holy Moly is not yet available on HBO Max.