Boynton Beach Club (2006)

A handful of men and women "of a certain age" pick up the pieces of their lives and look for new love after the loss of their mates in this comedy drama from writer-director Susan Seidelman. Jack (Len Cariou) married his high school sweetheart when they were still in their teens, and when she dies in her early sixties, he is emotionally devastated. Jack's friends and family insist he needs to start living again, and he begins attending a support group for bereaved senior citizens. Jack strikes up a friendship with fellow widower Harry (Joseph Bologna), who offers advice on making time with the ladies, something he's developed a strong interest in since his wife's passing. At their meetings, Jack makes the acquaintance of Sandy (Sally Kellerman), an attractive and intelligent woman who - via a number of obvious sexual advances - makes no secret of her attraction to Jack, though he isn't sure he's ready for a new relationship. Jack and Harry also cross paths with Sandy's friends Marilyn (Brenda Vaccaro), who recently lost her husband to an absent-minded driver with a cellular phone, and Lois (Dyan Cannon), who still flaunts her considerable sex appeal and is dating a younger man, Donald (Michael Nouri). Also screened as The Boynton Beach Bereavement Club, The Boynton Beach Club also stars Renee Taylor, Bologna's wife and frequent acting partner.