You can send your characters on dates at Amour , unlocked at level 5. You can use Couples Corner to send regular characters in your Entourage on dates with each other. There are 33 dates with 13 potential people to date currently available. You must complete the previous dates with that person to unlock the newer dates.
Christopher "Chris" Winters appears very early on in the game when your main character attends a nightclub shortly after joining Hollywood U in the quest " Ready, Set, Pitch! You meet Chris at the wrap party that Ethan manages to get you into, Chris attracts the attention of the barman and kindly buys you a drink. Chris returns later when he offers to loan you his beach house to shoot a music video for Lisa and again during the shoot of the video, where he offers to star in the video. Chris is either really impressed or really disappointed by how you leave his house looking after the shoot. From the moment he is introduced to your character, he shows an obvious attraction. Before becoming a big name, he lived on a farm in Missouri.