Sex and the Single Girl (1964) Timeline Explained – Every Event in Order

Bob Weston, a tabloid reporter, needs a way to get an interview with Dr. Helen Gurley Brown after she refuses to cooperate with Stop magazine. He hatches a plan to impersonate Frank Broderick, a client of Helen's, so he can attend therapy sessions as a patient and gather material for a story while also reporting back to the real Frank with Helen's marriage advice.

• bob weston
• frank broderick
• impersonation
• interview
• tabloid reporter

Bob fakes a suicide attempt to deepen his cover and get closer to Helen emotionally. The staged crisis is meant to manipulate the situation so Helen would let her guard down, allowing him to gather more personal information for his tabloid story. The ploy works too well, Bob ends up genuinely kissing Helen and realizing he's falling for her.

Foreshadowing: Earlier therapy sessions show Bob acting shy and smitten with Helen, hinting his feelings are becoming real.

• fake suicide
• manipulation
• therapy session
• emotional escalation

The intense emotional situation of the fake suicide attempt catches Helen off guard. While she initially maintains professional boundaries, the moment creates genuine vulnerability between them. Helen admits she's been attracted to Bob despite knowing he supposedly represents Sylvia's husband, and the kiss happens naturally from that building tension.

Foreshadowing: During earlier sessions, Helen insists on role-playing exercises where she acts as Sylvia, showing she's already emotionally engaged with Bob.

• kiss
• helen gurley brown
• attraction
• therapy session
• emotional moment

Helen panics after realizing she's falling for a married man. She seeks her mother's advice, who suggests she focus on helping Frank and Sylvia reconcile rather than pursue her own feelings. Helen arranges for Sylvia to return to work at Frank's office, hoping that fixing their marriage will resolve her own moral dilemma.

• sylvia broderick
• reconciliation
• marriage advice
• helen's mother

Bob asks Gretchen, a nightclub singer, to pose as his wife Sylvia to prove to Helen that he's not really married. When Gretchen cancels last minute for an audition, Bob's secretary Susan fills in as a backup. At the same time, Gretchen abandons her audition and also shows up at Helen's office. Three women end up claiming to be Mrs. Broderick simultaneously, creating chaotic confusion.

Foreshadowing: Bob had been pushing the lies further, arranging for fake wives to maintain his cover.

• gretchen
• susan
• bigamy confusion
• multiple women
• false identity

The confusion escalates when three different women claim to be Mrs. Broderick at Helen's office. Sylvia, realizing the situation has spun out of control, calls the police. Since it appears that Frank (whom they believe is visiting Helen) has multiple wives, Frank gets arrested on bigamy charges, completely unaware of Bob's impersonation scheme.

• frank broderick
• arrest
• bigamy
• police
• confusion

Helen visits Sylvia with Dr. Rudy DeMeyer, a physician she admires who has romantic feelings for her. Through their conversation, Helen discovers the truth: the man who has been visiting her office wasn't Frank Broderick at all, it was Bob Weston, the managing editor of Stop magazine. The revelation shocks her and explains why everything felt off.

Foreshadowing: Rudy has long harbored feelings for Helen since reading the original article about her.

• bob weston identity reveal
• rudy demeyer
• helen discovers truth
• stop magazine editor

After discovering he's been deceived by Bob, Helen is hurt and angry. Bob realizes his feelings for her are genuine and refuses to let Stop publish any story about Helen that would further damage her reputation. His editor sees this as a betrayal of the magazine's values, and Bob is fired for refusing to run the inflammatory piece.

• bob fired
• stop magazine
• editor job
• refusing story

When Helen learns that Bob has been lying to her the entire time, impersonating a married man to get information for a tabloid, she's devastated. The betrayal is overwhelming, and in her shock, she asks Rudy to take her away to Fiji, wanting to escape the entire tangled situation.

• helen goes to fiji
• rudy
• escape
• emotional response
• betrayal

The film culminates in a frantic chase through the city as both couples pursue each other in cars and taxis. At the airport, Frank and Sylvia reconcile and fly to Fiji to start fresh. Rudy and Gretchen, who have connected during the chaos, decide to travel to Hawaii together. Helen, having forgiven Bob, chooses to marry him in Las Vegas after he gets a new job at Dirt magazine.

• airport finale
• fiji
• hawaii
• las vegas
• marriages
• resolution