A couple years out of college, Cooper Barrett still doesn't have his dream job; he's possibly fallen for his across-the-hall neighbor, Kelly Bishop, and he can't seem to avoid major trouble, along with his roommates, Neal and Barry. Rounding out the gang is Cooper's older brother, Josh, who is constantly popping in to hang with the fellas and get some peace from his wife, Leslie, and their kids. Cooper struggles through the messy and hilarious disasters of life after college—a night in jail, crazy ex-girlfriends, going broke—giving us guidance so we can avoid the same mistakes.

When Kelly gets invited to her ex-boyfriend's wedding in Mexico, she doesn't want to show up alone – so she decides to bring Cooper as her plus one. But when getting to the wedding becomes a south-of-the-border logistical nightmare, Cooper enlists Neal, Barry, Josh and Leslie to come to their rescue.