Phillip is a wealthy quadriplegic who needs a caretaker to help him with his day-to-day routine in his New York penthouse. He decides to hire Dell, a struggling parolee who's trying to reconnect with his ex and his young son. Despite coming from two different worlds, an unlikely friendship starts to blossom.

High school guidance counselor Jeff and his platonic friend and co-worker Anne are responsible, well intentioned, kind… and boring. They frustratingly watch on as their peers find love and companionship, while they continue to fail in spectacular fashion when it comes to romance. As they reach their loneliness breaking point, they make a pact to forgo their familiar, vanilla personas in exchange for their unexplored, confident alter egos. They wave goodbye to Jeff’s awkward all-male book club and Anne’s flailing attempts to catch the eye of Jeff’s sexy neighbor Max, and say hello to raucous summer nights filled with booze, dancing, and sex. Naturally things don’t exactly go according to plan.