Comedy following Milo (Danny Masterson), a thirty-something who has recently ended a relationship with his girlfriend Lisa, and is trying to re-enter the dating scene with the help of his three best friends and co-workers, Tyler, Gibbs and Neal
The boys band together to help Neal overcome his shyness and salvage his chances with a new girl. They form a plan to manufacture another encounter between the pair at a party, but a miscommunication means Milo and Neal end up at one bash, and Tyler and Gibbs at another, very different event.
Tyler needs to prove his intellectual worth to earn the respect of the magazine's new writer, Jude. Elsewhere, Milo struggles with being an unemployed novelist.