A high school baseball coach (Krumholtz) and a down-on-his-luck private investigator (Burns) form a bond as they scour New York City for the coach’s wife, who’s run away with a second-rate rock star. As in Burns’ previous films, the city itself becomes a character as the two men confront their fear of change and the familiar habit of loneliness.
Johnny Rizzo, is about to trade his dream job in talk radio for some snooze-ville gig that’ll pay enough to please his fiancée. Enter Uncle Terry, a rascally womanizer set on turning a weekend in the Hamptons into an eye-opening fling for his nephew. Nice guy Johnny’s not interested, of course, but then he meets the lovely Brooke, who challenges Johnny to make the toughest decision of is life.
Hell’s Kitchen on Ash Wednesday, 1983. Rumors are flying that Francis Sullivan’s younger brother Sean, dead for three years, has reappeared. If he wasn’t killed by rivals, then old scores still need settling, putting Fran and Sean in danger. An upstart is pressuring the local mob boss, who’s Fran’s protector; Sean’s wife, who thinks she’s a widow, has gotten on with her life, but Sean has come back for her. The parish priest, part of the initial deception, is frightened. Bad guys with guns are closing in. Can Fran get Sean and his wife out of the city, avoid a war between rival factions, and hold onto new-found morality? Will the cross of ashes on his forehead protect him?
In New York City, thirty-three year old Patti Petalson is unhappy with her life. Her passion is literature, she having published one book of short stories ten years ago, but not having written anything since. Instead to earn a living, she sells real estate, a job and for a boss she hates. And although unspoken, she hates her husband, self-absorbed restaurateur Chazz Coleman, who doesn’t listen to her and does whatever he wants regardless of her. While out for dinner, Patti and her BFF, schoolteacher Kate Scott, run into Brian Callahan and Michael Murphy, who were once Patti and Kate’s respective boyfriends, the four who used to do everything together while they were in college, with both relationships ending twelve years ago as they were graduating. Kate has never forgiven self-described lowbrow Murph, now a successful lawyer despite his lack of academic smarts, for what she believed was a sexual indiscretion, while Murph outwardly just wants the opportunity to apologize. However, there is an unspoken attraction still between Patti and Brian. Brian is also somewhat unhappy with his current life. He is a successful writer of a series of what he considers “pulp fiction” detective novels, but has just written his first serious novel – one he doesn’t admit to anyone is semi-autobiographical in that its lead character is a man trying to rise to greatness out of mediocrity – which is being panned by the critics, with his fans refusing to read it. He is dating twenty-five year old record company executive Bernadette, the two of them who live in separate generations and as such don’t really understand each other. As Patti, Brian, Kate and Murph reconnect, the questions become whether there is a second life for them as couples, and specifically for Patti and Brian if their reconnection can elevate them into being the writers they truly want to be.
The story follows the misadventures and confusion of a groom (Ed Burns) and his four groomsmen the week before a wedding. Wrestling with issues of fatherhood, honesty and growing up, the five thirty-somethings discover their extended adolescence might be finally coming to a close.
Six New Yorkers have an interrelated series of relationships. TV producer Tommy, who’s just broken up with his girlfriend, has a short relationship with commitment-phobe Maria, who he meets in a video store, and also hooks up with married real-estate agent Annie, who he meets while apartment hunting. Annie is open to a relationship because her husband, Griffin, is cheating on her, which she slowly comes to realize through talking to her friend/co-worker who’s gone through the same thing. Griffin, a 39-year-old dentist, is cheating with 19-year-old waitress Ashley, who he picked up in a park; she realizes she can do better when Ben, a hotel doorman and aspiring musician, tries to pick her up, in a belated attempt to recover from his divorce a year ago from schoolteacher Maria (the same Maria from the video store). Most of these relationships seem driven more by a desperate need to be in a relationship than actual love.
How do siblings deal with each other in their targets? This is the question tackled in this movie. Blue-collared Mickey drives a New York taxicab since the breakup with his promiscuous ex-fiancée Heather two years ago. His younger, white-collared brother, Francis, cannot let Mickey forget the tragedy of the “hairy ass”: (Mickey’s image of his apartment floor of the guy having sex with Heather after walking in on them). Finding relief in driving his cab, Mickey meets an art student named Hope whom he marries after knowing her for only 24 hours. Mickey also meets his old lover Heather, and learns more about life itself as taxi fares in the course of a summer. Francis, a young Wall Street corporate raider, unhappy in his marriage to Renee and led by his infidelity, continues his shots at Mickey throughout the film, only to find himself a plot device that lends humor and lessons about marriage and brotherhood when he meets and starts an dangerous affair with Heather, despite Mickey’s warnings that Heather is a gold-digging nymphomaniac who goes through sexual partners as often as a person changes clothes. Given Mickey’s frame of reference on the past and his bride of 24 hours, it is no wonder that the two brothers, along with their father, an ego-eccentric and emotionally bereft bigot and a hard-core chauvinist who does not allow women aboard his fishing boat, learn about the strength of women, and their own lives.