Three days since leaving Christian, Anastasia “Ana” Steele has begun her job as personal assistant to Jack Hyde, an editor at Seattle Independent Publishing (SIP). He continually asks Ana out, making her uneasy, but writes it off. Christian emails her to see if she needs a ride to her friend Jose Rodriguez’s gallery exhibit in Portland, which she had forgotten about until Christian emailed her. The pair attend the show together and reconcile their relationship by kissing in an alley and visiting a restaurant together. Christian buys José’s portraits of Ana for selfish reasons, one is to prevent random people from buying them, and the second is for his own amusement.

Christian reveals to Ana that he has bought SIP, but the deal must stay secret for another month. Ana is furious that Christian is interfering in her career, especially after he freezes the company’s accounts preventing her from going on an overnight business trip to New York with Jack. Christian insists it was for her own protection, because Jack is a “known philanderer”, as he apparently harassed his last five assistants. Those suspicions prove correct when Jack corners Ana after hours and blackmails her, demanding sexual favors. Ana’s self-defense training allows her to escape. Christian has Jack fired and confiscates his work computer.

While attending a masquerade ball at Dr. and Mr. Grey’s residence, Ana meets Elena Lincoln (whom Ana nicknames Mrs. Robinson) for the first time and discovers that Elena and Christian own a salon business together. Later, Ana is auctioned off and Christian bids $100,000 for the first dance with her. Ana is disgusted that Christian continues to be friends with the woman who seduced him when he was only 15 years old, and initially introduced him to the BDSM lifestyle. When Elena realizes that Christian sees Ana as a girlfriend and not a submissive, she becomes antagonistic towards Ana, trying to sow discord in the budding relationship.

Ana is stalked at work by a disturbed Leila Williams, one of Christian’s former submissives. Ana’s fear intensifies when she discovers that Leila has a gun. It is revealed Leila’s obsession began after her lover died in a car crash four months before, leading to a mental breakdown. Leila breaks into Ana’s apartment and threatens her at gunpoint. Christian defuses the situation by utilizing their dominant/submissive dynamic, but this leaves Ana worried that Christian cannot be satisfied with a vanilla relationship. Ana confronts Christian about Leila. Fearing she is leaving him again, he impulsively proposes, but Ana needs time to consider it.

José drives to Seattle to visit Ana. Christian still views José as a romantic rival, and only permits Ana to see him if they both stay at Escala. Ana becomes worried on the night before Christian’s 28th birthday when he goes missing while flying from Portland to Seattle in his helicopter with Ros Bailey. However, he eventually makes it back to Escala safely, and explains that both helicopter’s engines failed; sabotage is suspected. Ana realizes she never wants to be without him and accepts his marriage proposal.

The next day, the Grey family throws Christian a large birthday party at their mansion. Kate worries about Ana after finding an email between Ana and Christian, discussing the BDSM Contract. Ana assures Kate that her relationship with Christian is a vanilla one. After Christian and Ana announce their engagement, Elena angrily confronts Ana, accusing her of being a “gold-digger”, and claims a vanilla relationship will never satisfy Christian. Grace Grey, Christian’s adoptive mother, overhears the argument and is furious that Elena preyed on her teenage son. Elena leaves in disgrace and Christian decides to end their business relationship.

Christian takes Ana to the boathouse, which is decorated with flowers and soft lights. He proposes properly with a ring and Ana accepts. Outside the Grey’s mansion, Jack Hyde is secretly watching the party; he reveals that he sabotaged Christian’s helicopter and swears revenge.