Life sucks. Gabe Harris has been clued into this fact for a long time now. In his mid-twenties, life has been nothing but low paying jobs, petty power-tripping bosses, and the worst roommates mankind has to offer. Bills, debt, and misery have haunted him for his entire adult life and, to make matters worse, it feels like his dream of being a writer is dead on arrival. One fateful night, he decides to take control of his life and make his dream a reality.

In a few short weeks, Gabe's life has changed completely. He went from working nightmare jobs and living with awful roommates to a small studio apartment that was intended to be all his own to renting a house on a quiet street and sharing it with the woman of his dreams as he began to seriously pursue his ideal job. But the changes are far from over. Gabe now finds himself in the company of a staggeringly attractive redhead, Holly. For all her beauty, she is shy, awkward, and at just as unhappy a place in her life as he was not all that long ago.

Gabe's life is still changing. He can no longer claim that it sucks, but it is busier than ever before. Between balancing his relationships with Ellen and Holly, trying to get a writing career off the ground, and learning what it means to have the affection of a seductive tattooed beauty and a shy cougar, he can hardly seem to find a minute to himself. Not that he's complaining. Only now it's about to get even more complicated. Chloe, a goth gamer girl, is looking to get involved with the rather unconventional household he now heads up...

After months of flirtatious teasing, Gabe suddenly finds himself in the presence of Krystal, the tatted redheaded goddess. Making the drive down, she has thrown herself into his life, thrilled to have some fun and relaxation. Only it's not that simple, because it's never that simple. Fun and carefree as Krystal appears, Gabe (and Ellen) suspect that her and her tomboy girlfriend Liz are testing the waters for a relationship. Not that they particularly mind.

Everything is changing for Gabe. His writing career is seeing some traction, his relationships are blossoming, and the time has come to move to a new, bigger house. Krystal and Liz are ready to commit to a new life living with and dating him. But Gabe was never under the impression that loving five women simultaneously was ever going to be easy.

Gabe Harris is the man with five lovers. Since reconnecting with Ellen, he has begun dating four more women, has one theoretically waiting in the wings, and has begun relationships of varying casualness with four more women. He has been doing his best to craft a new life. Not just for himself, but for the women he loves. And he's been doing good. All of that comes to a crashing halt when he remembers Valentine's Day is right around the corner. And now, Gabe finds himself facing the most difficult, arduous challenge of his entire life: planning Valentine's Day dates for ten women. In a row.