Neil Truman seems to have it all. Gorgeous home. Beautiful wife and daughter. Lucrative job as an investment banker. It's the American dream - so why isn't he happy? The truth is that nearly two decades of marriage and years of 80 hour work weeks spent helping the rich get richer have left Neal feeling like he's missing...something.
Disillusioned by his seemingly perfect life and fed up with his career, the final straw comes when he's tasked with flying to New York last minute to sign a new client, only to be stranded on the tarmac in flight-delay hell. After suffering one too many indignities, Neil has a moment of clarity: he doesn't need this shit. So after blowing a an epic fuse, becoming an internet hero and quitting his job in spectacular fashion, Neil rushes back to share his epiphany with his wife Grace. That's when he catches a glimpse of her in the throes of passion with another man. Simon.
Flashback six months, to Grace bombing an interview for an interior design job at a firm headed by a kid 15 years her junior. Grace was on a much different path once, but she gave up the promise of a Fulbright scholarship and a career in the arts to start a family with Neil. Not that Grace would tell you she regrets her decision...she just didn't think that taking time off to be a mother would put her ambitions out of reach. But now, as her marriage has become a little too familiar and her old dreams have begun to fade in the rearview, she's started to feel as empty as the open houses she stages part time. So when a night chasing excitement leads to Simon, she decides to see where this new path will lead.
But back in the present, all Neil knows is what he sees in front of him. Furious, he confronts Simon, only to learn the more shocking truth. This isn't some torrid affair; it's a professional arrangement. Grace is seeing a male escort.
Reeling, Neil considers confronting Grace, but when he inadvertently winds up with Simon's phone and gets a call from one of his clients, Neil decides to try out the escort business for himself. And while he gets off to a slow start, he soon learns that not only does he have a knack for the business, but that his new side gig might just offer the enlightenment he's been seeking. But one night of adventure won't fix a lifetime of problems, and as if the hole in his marriage and his daughter's growing pains aren't enough, he'll also have to deal with Adriana, a local madam whose intentions for Neal are murky. And then there's Simon, who isn't too pleased to have his business stolen out from under him...and isn't afraid to make things a lot more difficult for Neil.