Three days after leaving Christian Grey, Ana began her job working as a personal assistant to Jack Hyde, and editor at Seattle Independent Publishing (SIP). He continues to ask Ana out, but she turns him down. Christian began emailing her to see if she needed a ride to her friend Jose Rodriguez’s gallery exhibit in Portland. The couple reunited and reconciled after attending the show together. Christian buys Jose’s portraits of Ana to prevent that random people buy them, and because it amuses him.
Christian reveals to Ana that he has bought SIP, but it must stay secret for another month. Ana gets mad that Christian is interfering in her career, especially since he froze the company’s accounts preventing her from going on a business trip to New York with Jack. Christian tells her that it’s for her own protection since Jack apparently harassed his last assistants. It turns to be true when Jack blackmails Ana, demanding sexual favors. Ana has had some training in self-defense from her stepfather who is ex-military, which allowed her to escape. Christian fires him and confiscates his work computer.
While attending the masquerade ball at Dr. and Mr. Grey’s home, Ana meets Elena Lincoln, the woman that introduced Christian to the BDSM lifestyle and she discovers that she and Christian own a salon together. Later, Ana is auctioned off and Christian bids $100,000 for the first dance with her. Ana is angry at Christian because he continues to be friends with Elena.
Ana is stalked at worked by Leila Williams, one of Christian’s former submissive. Ana becomes frightened of her when she discovers that Leila has a gun. Leila reveals that her obsession began four months ago when her lover died in a car crash, leading to a mental breakdown. Leila breaks into Ana’s apartment and threatens her with a gun. Christian fixes the situation leaving Ana to fear that Christian can’t be in a vanilla relationship. Ana confronts Christian about Leila. Scared that Ana was going to leave him, Christian proposes, but she takes the time to consider it.
Jose drives to Seattle to visit Ana. Christian still does not trust him, so he only permits her to see him if they both stay at Escala. Ana becomes worried the night before Christian’s birthday because she hadn’t heard from him since he went flying from Portland to Seattle. He makes it back safely, explaining that the helicopter’s engine failed. Ana realized that she never wants to live without Christian and accepts his proposal.
The next day, the Grey family throws Christian a birthday party at their home. Kate, her roommate, becomes concerned when she reads an email between Ana and Christian talking about their BDSM contract. Ana tells Kate that their relationship is a vanilla one. Christian and Ana announced their engagement and Elena confronts her for being only interested in Christian’s wealth and that a vanilla relationship will never satisfy him. Dr. Grey overhears the conversation and is furious that Elena preyed on her son. Elena leaves the party and Christian decides to end their business relationship.
Christian takes Ana to a boathouse where he properly proposes to her with a ring and Ana accepts. Outside of the Grey mansion, Jack Hyde is secretly watching the party and reveals that he sabotaged Christian's helicopter as an act of revenge.