A widowed businessman becomes obsessed with one of his employees, the divorcée Betty Preisser.
Fifty-six-year-old Jerry Kingsley (Frederic March), the co-owner/co-operator of Lock Lee Fashions, a New York-based garment manufacturer and wholesaler, has been widowed for two years. His older spinster sister, Evelyn Kingsley (Edith Meiser), moved in with him in his apartment following Jerry's wife's passing to take care of him, she who has always assumed the role as family caregiver. One of Jerry's married daughters, 25-year-old Lillian Englander (Joan Copeland), believes Evelyn has a neurotic fixation on Jerry, Lillian unaware that her own fixation on her father is just as strong. Evelyn tries to arrange dates for Jerry, primarily with lonely widows, something he resists in wanting to find a woman on his own despite his own loneliness. Unlike his married business partner, 59-year-old Walter Lockman (Albert Dekker), who is always chasing after "tootsies" and "floozies," Jerry wants someone to love. After learning her story, Jerry thinks he's found the woman in Lock Lee's 24-year-old receptionist, Betty Preisser (Kim Novak). Betty, who never had much parental guidance, recently got divorced from her musician husband, George Preisser (Lee Philips). There had always been a strong physical attraction between Betty and George, but nothing that she would now consider love. Betty is an extremely sad and confused woman, admits that she misses George, but doesn't want to get back together with him, she needing the antithesis of George as the person in her life at this point in time. Jerry and Betty enter into what ends up being a turbulent May-September relationship, their issues based on their own insecurities: Jerry, who realizes that his love for Betty is illogical due to the differences in their ages, admits he will always have pangs of jealousy in believing that she will be more physically attracted to men her own age; and Betty doesn't know if what she feels for Jerry is love or just a sense of being protected, something she never felt with George. Regardless, they decide to get married. That announcement opens up their relationship to the scrutiny of his family and friends, her family and friends, and their co-workers. The situation gets even more complicated when George reenters Betty's life. The questions then become if Jerry and Betty's relationship can withstand all these pressures, or if there is a factor or factors that will show them that their relationship makes sense at this point in their respective lives.—Huggo
Betty Preisser (Kim Novak), an attractive 24-year-old divorcee, works as a secretary in the hard-boiled atmosphere of Manhattan's garment district. Her workaholic boss Jerry (Frederic March) is feeling his own mortality. He's overworked and lonely. He's a 56-year-old widower, but still enmeshed in his family obligations. His bossy older sister Evelyn(Edith Meiser) has moved in with him and he has a married daughter Lillian (Joan Copeland) and grandchild who live nearby.
Betty hasn't been feeling well lately and has been typing at home. Jerry comes to her walk-up on the downscale far East Side to pick up some papers. She tells Jerry she's upset about her divorce. Ordinarily, Jerry would tune out an employee like her, but he's lonely and he feels empathy for her. He comes inside and she pours out her heart to him. She and her husband George (Lee Philips) married because of sexual attraction and because all her friends were getting married. But her ardor cooled off pretty fast and eventually his did, too. He got a job playing the piano in Las Vegas and the marriage ended. She's a conventional young woman without a lot of insight into her own behavior. She's living with her mother (Glenda Farrell) and now she regrets that the marriage ended. Jerry gets pulled into her story; she makes him feel needed in a way that his family doesn't. He gives her fatherly advice: stop feeling sorry for yourself and start dating again so she'll meet a "nice young fella." But he's the one who falls for her.
Later, at dinner at his daughter's, he tells his sister and daughter (Joan Copeland) about her. His sister's ears perk up; she's no fool. Betty also models for Jerry's dress company. Jerry has a co-worker Lachman (Albert Dekker), who's a real dirty old man. He's what Jerry's afraid he'll become if he gives into his infatuation with Betty. Jerry gets obsessed with Betty. He just "happens" to walk past her building and casually run into her by "accident." Betty, not the brightest bulb on the tree, is happy to be the object of his attention. "Jerk! Jerk!" Jerry slaps himself on the forehead. He knows he's stepping in quicksand.
In the meantime, Jerry's daughter Lil is having problems in her marriage. Her accountant husband Jack (Martin Balsam) feels that they don't communicate that well anymore. She resents Evelyn and wants Jerry to move in with her and Jack. She knows her father is involved with a woman and resents that he hasn't talked to her about it. She accuses Evelyn of trying to prevent Jerry's "middle-aged fling" (little does she know). She's actually projecting her own feelings on to her aunt. She's the one who can't separate from her father.
Betty tells Jerry that their relationship has to end. She's afraid that "somebody's going to be hurt." She's not super bright, but at least she realizes that she's jeopardizing her job and she isn't really interested in him. He tells her about his hardscrabble immigrant childhood over dinner in a restaurant. He knows his emotions are out of control and doesn't know why. "You simply don't find me attractive?" he asks wistfully. Betty has the decency not to be a gold digger. But Jerry can't let go of her. He tells her he loves her. They go back to the office so he can cut a dress pattern. He keeps on telling her his life story, about union organizing and how he went to night school and studied dressmaking. He grabs her and starts to kiss her. "I don't want to hurt you!" she cries out. But since we've already learned that she acts out sexually, she gives in.
Now Betty has her own little secret from her co-workers. It's love on his part, but not on hers. Jerry wants to take her to his cabin on Lake George and buy her a mink coat. Betty's being put to the test. She's a basically decent person, but no saint. He asks her to marry him. Jerry's in dream world. She flips out on him and tells him he makes her feel "like a tramp." He tells her to stop her tantrum. She cuddles up to him. He wants a sex partner; she wants a father figure to replace the dad who walked out on her when she was six. She's willing to listen to all his boring stories because it makes him seem like a dad. He asks her to marry him and she reluctantly says yes.
Betty's worried about how Jerry's kids are going to take the news of their marriage. "My whole life is a joy since I met you--you're an obsession, that's what love is," Jerry says passionately. His and Betty's family feel differently. Jerry finally meets Betty's mom. Betty's mom is a tough cookie. She's self-centered and neglectful--"Kids are more bother than they're worth." She confronts Jerry about being an "old wolf." She calls him a dirty old man who ought to be in jail.
Now it's time to tell Jerry's kids and sister. Jerry demands that Evelyn cook a family dinner so they all can meet her. At the family dinner, everyone is carefully polite to Betty. Lillian comes around and there's also a pre-wedding celebration at the dress company. Jerry's happy as a clam. But he tells Betty if he's ever bad-tempered it's because he's afraid of dying. Betty goes back to her mom's apartment. Her dour mother and friend Marilyn (Lee Grant) are sour-faced and jealous. "I like having a fuss made over me!" gloats Betty. But Marilyn warns her that after one year she'll be "crying her eyes out and talking about sticking her head in the oven." She wants Betty to get back together with her ex George--"You love this old man?!!" She confides her fears to Marilyn--Jerry's jealous and moody and it scares her. She's getting into the same emotional knots that she got into with her first husband.
Jerry's getting old and cranky. He's no longer the good boss he used to be. He's yelling at his co-workers. His relationship with Betty starts to go sour. She's bored and just as moody as him. They go out and run into a musician friend of George's. He's back in town. Now she's torn. Jerry's jealous and obsessed with her, now the negative side of his fixation on her is coming out. Betty says maybe they should call the whole thing off. Jerry's terrified of losing her. George shows up at Betty's mom's apartment. He's got a potential steady music gig. He's young and handsome, a good physical match for her. Betty's mom and sister like George. He's one of them. They have a beer and start talking. He's an emotionally unmoored person like she is. He wants Betty back. He kisses her and she's tempted. "I'm tired of being desirable!" she cries out. She hints at suicide and asks George to help her run away.
Betty meets up with Jerry in a playground in the snow. She tells Jerry he'd be better off without her because she and George had made love. Jerry falls to pieces. He (finally) realizes he's made a fool out of himself. He sees her at last for the emotionally needy rootless person that she is. Jerry comes back to his apartment out of the snow. Evelyn makes a big fuss over him, like the big sister she is. He tells her that it's over and that Betty was "candy" and that he's too old for "candy." His fantasies are destroyed and he's now really bitterly lonely and bereft. He sits in an easy chair with a shawl around his legs, alone. He gets a phone call, his friend Lachman has committed suicide. Becoming like Lachman is Jerry's worse nightmare. Jerry goes back to Betty's apartment. They fall into each other's arms. They're both flawed individuals, but they're looking for happiness wherever they can. Will they end up being happy? Will Lillian sit back and let Betty inherit Jerry's money? Will Evelyn give up living in the Upper West Side apartment and move back to Brooklyn? Will Betty's mom and friend Marilyn stop undermining Betty? And can Betty stop having sex with George? Their happiness may be short-lived.