Relationships[]
Like Stottlemeyer, Disher used to be wary of Monk's abilities, but as the series progressed, he came to admire and respect them.
During his life, Disher loses his entire life savings during a trip to Las Vegas ("Mr. Monk Goes to Vegas"), acts once as Natalie Teeger's bodyguard ("Mr. Monk and the Election") and helps Monk find clues for the Trudy Monk case by traveling to New York with him ("Mr. Monk Takes Manhattan"). Randy argues regularly with (but is also not-so-secretly attracted to) Monk's first assistant, Sharona Fleming, and he maintains a friendly, professional behavior towards Monk's second assistant, Natalie Teeger. He seems to always harbor crushes on Monk's assistants. For instance, in "Mr. Monk and the Paperboy", he writes a personal ad fitting Sharona's profile, which he tries very badly to hide from her. In "Mr. Monk and the Bad Girlfriend," Natalie mentions to Randy at one point that she and Monk have news. He thinks that she means to say that she is in love with him, and Natalie is left in a dumbstruck state while Monk explains to Randy their theory that Linda Fusco killed her partner.
His lack of luck getting dates is so notorious that when he does get a girlfriend, nobody believes him. In "Mr. Monk and the Employee of the Month", he shows the cast a generic picture of a woman. Sharona confirms that it was included with his wallet. They dismiss his claims that his girlfriend is a wallet model named Crystal Smith. It is revealed that Randy was telling the truth. (Monk: "Mr. Monk and the Employee of the Month")
He also dates a woman who turned out to be using him to kill Monk, so that Monk wouldn't testify against the head of the gang she was a member of. (Monk: "Mr. Monk Gets Cabin Fever")
With Sharona Fleming
- In "Mr. Monk and the Candidate," Randy lingers behind after Stottlemeyer fires Monk from the case, leading Sharona to bitterly ask, "What is that, your tough look?"
- In "Mr. Monk and the Psychic," Sharona snaps, "Bite me," after Randy makes a cutting remark about her trying to "take care of business first." He later mocks Monk's abilites while they chat at a memorial service, saying "Sure," sarcastically when she tells him the number of calls they'd been getting.
- In "Mr. Monk and the Billionaire Mugger," Randy comments, "A little short, huh?" when Sharona tries to get him to sign a check quickly. Sharona retorts, "Yeah? So are you."
- In "Mr. Monk and the Marathon Man," Randy suggests that painting toenails only halfway is a new style. Sharona mutters "Like you know," under her breath.
- In "Mr. Monk and the Red-headed Stranger," the captain has broken his arm, leaving Randy in charge. When Randy explains this to Monk and Sharona, she scoffs, "Oh, my God." Randy sarcastically replies with "I'm so glad you're here!"
- In "Mr. Monk Goes to Mexico," the Mexican version of Randy - Lieutenant Plato - shows some interest in Sharona, though not in the style the real Randy does later.
- In "Mr. Monk Goes to the Theatre," Randy stops to ask Sharona if she's okay when rushing over to a culprit.
- In "Mr. Monk and the Sleeping Suspect," they flirt for a second when she arrives at the crime scene, Sharona teasing him about a supposed girlfriend. Randy stares at Sharona momentarily when she stands next to him throughout the episode. Later, she has plans to leave for New Jersey, and asks teasingly if he'll miss her, to which he awkwardly admits he would - "maybe a little."
- In "Mr. Monk Meets the Playboy," Randy attempts to possibly impress Sharona by finding a set of pictures she'd wanted to keep mostly private and burning them. This backfires when Sharona, doubtful, asks if he looked at them. Caught off guard, Randy freezes and stares at her for a full ten seconds before walking off, Sharona looking after him.
- In "Mr. Monk and the 12th Man," Randy tries teasing Sharona the way she usually does with him about her newest boyfriend: the deputy mayor, Kenny Shale. He does this for most of the episode, and is obviously jealous when she tells him about the dates Kenny takes her on.
- In "Mr. Monk and the Paperboy," Randy and Sharona are stuck talking to Kevin at the beginning of the episode, both somewhat amused by the random things he's going on about. Randy laughs silently and Sharona glances at him, grinning. Later, she finds and reads aloud a personal ad he'd been trying to hide in the newspaper: "Man with a badge in hot pursuit of romance. I'm 32, fit, sexy, ambitious with a dynamite sense of humor. Looking for petite blonde, no-nonsense attitude, kids okay." Sharona quickly realizes it's meant for her and he denies it. She brings it up again later at a crime scene and they look at each other for a few seconds.
- In "Mr. Monk and the Three Pies," Randy jokingly pulls a check away from Sharona while handing it to her; she is not impressed. Later, while she's digging through a pie in order to find a bullet, he wanders over to her and says, "You know, this is one of my fantasies. Except it's not a pie...and you're not in it," to which Sharona exasperatedly replies, "Will you shut up?"
- In "Mr. Monk and the T.V. Star," Randy, jealous, watches for a minute as Sharona talks to Brad Terry, pretending to be reviewing notes when she glances over. He's completely distracted when Monk tries to talk to him and is clearly still looking to see where she went. Later, at a party, he makes his way over Sharona and asks her to dance, which she seems taken aback by. Sharona eventually leaves to dance with Brad, despite turning him down on account of not being "much of a dancer."
- In "Mr. Monk and the Missing Granny," she teases him about his allergy to cats briefly, saying she should get a cat. "At least you won't be alone on Saturday nights," Randy quips in response to this. She pokes fun at him again later in the captain's office when he is left behind at an interrogation. At the end of the episode, Randy's allergy turns out to be the key to the case. Sharona smiles at him and congratulates him.
- In "Mr. Monk Gets Married," Randy drunkenly tells Monk and Sharona he loves them, to which Sharona nods and says, "Okay." She makes several comments to Monk throughout the episode that she feels sorry for Randy and that they have to help them. She teases him once at the end of the episode, saying he can't even get his own mother to go home with him.
- In "Mr. Monk Takes Manhattan," Randy suggests that he and Sharona share a hotel room. Sharona scoffs in response, saying, "In your dreams." Later, he stutters when introducing her.
- In "Mr. Monk and the Panic Room," Randy offers to follow Sharona to the kitchen when she wants to feed a chimpanzee accused of murder. She immediately asks why, and he freezes for a minute before giving an excuse. They argue a bit throughout the episode regarding Sharona's attachment to the chimpanzee. She teases him later about a theory of his.
- In "Mr. Monk and the Blackout," Randy bursts into Monk's apartment during a blackout, immediately yelling, "Sharona, you okay?"
- In "Mr. Monk Gets Fired," Sharona practically tackles the commissioner for evidence, and Randy is visibly impressed.
- In "Mr. Monk Meets the Godfather," the entire subplot of the episode is Sharona's newest boyfriend, Fat Tony Lucarelli, and Randy's various attempts to get her not to date him. He even says at one point that he gets why she's attracted to him: he's dangerous. He goes on to add, "Some people think I'm dangerous." Sharona is somewhat amused and dismisses it. At the very end, he has to prove to her that Fat Tony isn't a good person by showing her a tape. He asks if this means she might not tease him as much. Sharona grins and replies, "No chance of that," and walks away still smiling. Randy looks proud of himself. (An important detail is Randy's use of the name Tony at the end of the episode, which is significant to the scene considering Randy referred to him as "Fat Tony" for most of the episode, despite Sharona constantly telling him not to.)
- In "Mr. Monk and the Girl Who Cried Wolf," Randy brings Sharona coffee after she supposedly sees a body, and tries to make a joke about what type of screwdriver she saw - Sharona is unamused. When she later finds Monk, Stottlemeyer, and him with the contents of her purse, grabs it, and stalks out, crying, Randy does nothing to comfort her. This is part of their complex relationship: while Randy clearly cares for Sharona, most of the time he tries to hide this or perhaps "get the upper hand" in their arguments/banter, which usually fails. A lot of the time he's trying to appear more - for lack of a better word - superior, or pretend he doesn't like her. Still, he stops to check if she's okay later in the episode and awkwardly compliments her story title.
- In "Mr. Monk and the Employee of the Month," Sharona teases him about a girlfriend he mentions, suggesting that she's imaginary. She then offers to come with as he interrogates someone, simply so he can "tell her all about Crystal, the famous wallet model." At the end of the episode, Randy tries to get everyone to see Crystal in a passing taxi, but Sharona walks off still skeptical.
- In "Mr. Monk and the Red Herring," Sharona has left for New Jersey with Trevor. Randy rolls his eyes and grimaces when she is mentioned by Stottlemeyer, trying to force a smile after Stottlemeyer looks suspiciously at him.
- In "Mr. Monk is On the Run: Part 2," Randy brings in a bouquet of flowers to Natalie, stopping for a second when he reads the tag. The flowers are from Sharona, and she and Benjy are flying in for Monk's funeral. This implies Randy and Sharona spoke over the phone offscreen, and Randy is still momentarily affected seeing the tag again.
- In "Mr. Monk and Sharona," Sharona returns to San Fransisco for a few days regarding an uncle's death. She stops in to surprise Stottlemeyer first, but halfway through their reunion Randy bursts into the room, asking loudly, "Is she here?" to no one in particular. They hug quickly, gripping each other's arms for a few more seconds. Sharona smiles and tells Randy it's great to see him, which he doubts, considering that she used to always tease him. He admits somewhat awkwardly that he missed it, and they continue to smile at each other, not looking away when Monk and Natalie enter the room. Randy is still completely focused on Sharona, enough that he forgot a rap sheet he was holding. She later interrupts him at work to try and rant about how awful the case is going, saying how she remembered always feeling good after talking to him. Clearly affected by this, Randy lets her walk him to the elevator. She makes a comment about how her and Natalie have been fighting, but she knows Monk likes her better, because "A woman always knows...who likes who." They both stare at each other as the elevator doors close. By the end of the episode, Randy is Sharona's ride to the airport. They share a quick kiss as he helps her into the car, leaving Monk and Natalie staring after them in shock.
- In "Mr. Monk and the End: Part 1," Natalie notes a pair of plane tickets to Newark in Randy's pocket, which are clearly to visit Sharona, but he dismisses them as personal and something they can't talk about at a crime scene.
- In "Mr. Monk and the End: Part 2," Randy is talking to Sharona over the phone to let her know how Monk is. He ends the call with "I love you," and when Stottlemeyer asks him about it, claims he was talking to the deputy commissioner. Later, Stottlemeyer is trying to find a siren in his car while they frantically drive to find Monk. Randy admits to selling it as well as having a yard sale. Stottlemeyer ends up finding a letter Randy had held on to all week, saying that he was leaving the SFPD to be police chief of Summit, NJ. After Natalie hints she knows why he's going to New Jersey, Stottlemeyer manages to guess Sharona. He says that now that he kinda knew they would end up together, now that he thought about it, and that it was perfect. At the end of the episode, Randy moves in to his new office with a picture of Sharona already on his desk.