|Season Three:||Into the Woods|
Rosa Diaz and Ray Holt are police colleagues who met in the Pilot when Holt becomes captain of the 99th precinct. The two share many similarities such as both are hard to read and can be intense at times. They became close when Rosa started dating Holt's nephew, Marcus.
Their friendship continued to develop even after Rosa broke up with Marcus. At one point in season 3, Holt invited Rosa to walk into a frozen lake with him to celebrate Christmas. Holt also helped Rosa when her fiancé's life was threatened and he had to flee.
They have also worked many cases together and seem to have similar ideas on what to do in them.
- Rosa and Holt meet for the first time
- Terry describes her to Holt as "Rosa is said to be tough, smart, hard to read, and really scary"
- Holt and Rosa both attend Amy's thanksgiving
- Holt lectures Rosa and Amy when Gina makes an official complaint about them for not solving her burgulary
- Holt convinces the pair to help Gina as she is frightened
- Terry and Holt intentionally annoy Rosa to prevent people from going to the toilet due to their fear of passing her
- Holt invites Rosa along with the squad to his birthday party
- Holt tells Rosa that she has embarrassed Officer Deetmore and he has complained. However he is willing to drop all charges if she apologises
- Holt asks Rosa if she has apologised yet. She says she had drafted a letter but Holt reveals that he read and destroyed it due to it's "Graphic nature"
- Holt helps Rosa make a sincere apology: "I'm sorry"
- Rosa complains that Deetmore rejected her apology. Holt tells her that she needs to be a leader and help him
- Holt tells off Rosa and Amy when they take Terry (roleplaying as a young boy for a drill) on a bouncy castle due to not taking the drill seriously
- Rosa is enlisted to help Holt win his bet with Peralta
- Holt's nephew, Marcus comes to visit and Rosa instantly takes a liking to him
- Holt is asked by Marcus to ask Rosa if she is single. Holt tells Rosa that it's silly for Marcus to ask him to send messages and Rosa agrees. Rosa then tells Holt that if Marcus wants her number then he has to ask her personally. Holt is left wondering who will tell Marcus
- After spending the night with Marcus, Rosa awkwardly interrupts Holt and Kevin whilst they are having breakfast
- Holt tells Rosa that if she wants to date Marcus it would be okay. Rosa says that she might want to but she definitely doesn't want to talk to Holt about it and he agrees
- Holt challenges Rosa, Amy, Terry and Gina to solve an unsolvable puzzle in exchange for Beyoncé tickets.
- Holt and Rosa are forced to double date
- The pair intentionally avoid spending time just the two of them to avoid getting to know each other personally
- Holt helps Rosa leave due to a pregnancy scare
- Holt deduces that Rosa wants to break up with Marcus from her body language
- Holt tells Rosa that she should be kind to Marcus in their breakup and be more respectful of his feelings
- Rosa and Holt both cry over Rosa's sadness about the breakup
- Holt invites Rosa to walk into a frozen lake to celebrate Christmas
- Holt and Rosa co-star in Gina's video on the 99th precinct
- Captain Holt, Rosa, Amy all take a bomb defusing course
- Rosa says that Kevin and Holt's anger doesn't come from the maths puzzle and that they just need to "bone"
- Holt becomes angry when Rosa instructs him on how to resolve his argument
- Holt and Rosa go for a run on the treadmills together although Holt doesn't realise that Rosa is extremely hungover