Thom is a forty-something advertising creative director with all the trappings of success: a roster of big-name clients and a shelf of trophies for his work, a beautiful house in the woods within an easy commute of New York City, a loving wife he is still attracted to, and a six-year-old son he adores. So why isn't he happier? Maybe because he is aging out of an industry that is obsessed with youth, or the mood stabilizers he's on are destroying his sex drive, or he's terrified that his generalized dissatisfaction is messing up his kid. And yet he bravely soldiers on, trying his best to at least maintain a state of happyish.
An artist and mother who makes a great home for her husband and son, Lee is appealing and sexy in a real way. She loves her happiness-challenged husband, and they have a good marriage. But she has some demons of her own, including a tense relationship with her meddling mother, who induces Jewish guilt at every turn. Lee is not above having an epic freak out every now and then to take the edge off.
Thom and Lee's sweet, adorable son and the apple of their eye is nonetheless plagued with the family curse. He's easily frightened, intimidated by his peers, and has trouble finding his own bliss, which exacerbates his parents' fear that they are somehow screwing him up.
Thom's immediate boss and close friend is trying to adapt to the new corporate paradigm rather than fight it. In his fifties, he has taken to wearing skinny jeans in an effort to fit in with the perpetually younger-skewing advertising industry. But he's in a difficult position as 'management,' and his advice that Thom change with the times or face the consequences does not go over well.
A smart, straight-talking headhunter and friend of Thom's, Dani is convinced that Thom shouldn't let the pursuit of happiness interfere with his life.