Fifty Shades of Grey
- Christian and Ana meet: Anastasia Steele interviews Christian Grey for the college newspaper, meeting him for the first time at his company, Grey Enterprises Holdings, Inc. They later have a run-in at the hardware store where she works, and Christian agrees to do a photo shoot for the article in the college paper.
- He starts courting her: Christian invites Ana for coffee, where he decides to distance himself from her. Unable to stay away, Christian sends her first-edition books as a gift. He then rescues a drunk Ana from a club and sobers her up in his hotel room. This is the first time that they share a bed! Leaving his hotel room, Christian and Ana kiss for the first time in the elevator. He later asks her out and flies her to his apartment in his helicopter, Charlie Tango.
- He takes her virginity: Christian and Ana have sex, Ana's first time. The next morning, she meets Christian's mother, Dr. Grace Trevelyan Grey. Ana reviews the contract that Christian has drawn up, stating the parameters of their relationship as dominant/submissive.
- They define the relationship: Christian meets Ana's father at her college graduation, where she also agrees to become his submissive (although she has yet to sign the contract). As a graduation present, Christian buys Ana a car. Later that week, Ana meets Christian's family when they attend dinner at his childhood home. Christian flies to Georgia to see Ana, where he meets her mother, Carla. Before leaving, Christian invites Ana on a date where they go gliding; this is the first time he refers to her as his girlfriend.
- They break up: Christian takes Ana to the Red Room for the first time. At her request, he shows her the extent of his "punishments," causing her extreme pain and forcing her to reevaluate their relationship. Ana tells Christian that she loves him, to which he responds negatively. Distraught, Ana breaks up with Christian.