Sharona Fleming/Relationships (2024)

Overview

History

Relationships

Family[]

Gail Fleming[]

Sharona and Gail tend to bicker a lot, as siblings would, as is shown in "Mr. Monk and the Earthquake." Throughout that episode they fight over almost everything: men, caller ID, handbags, and Monk. However, they still care about each other. In "Mr. Monk Goes to the Theater," Gail is arrested and Sharona does everything in her power to prove her innocence. Gail is mentioned several times throughout the series, despite only being seen twice, usually as a place for Benjy to stay, and it's mentioned that Sharona was talking to her on the phone in "Mr. Monk and the Paperboy," so they clearly have a healthy relationship.

Significant Others[]

Randy Disher[]

Throughout season 1, Randy makes no move to hide his distaste for both Sharona and Monk, openly bickering with her at crime scenes every other episode. As the series went on, he gradually comes to appreciate the two of them and by mid-season 2, he has developed a crush on her and is doing an awful job hiding it--much to her teasing. They continue to bicker upon meeting at the police station or crime scenes, though now in a more flirty manner, up until the point where she leaves unexpectedly to return to New Jersey with her ex-husband Trevor. Up to this time, Randy's crush is depicted as strictly one-sided, save for a few affectionate moments hinting her feelings towards him. (In the non-canon novel "Mr. Monk and the Two Assistants," Sharona compares their flirtation to the relations she has with cashiers or mechanics, but despite her claims, there were several encounters where the "erotic tension" Randy went on about would be more fitting.)

When Sharona comes back to San Francisco after her uncle Howard died, Sharona and Randy embrace fondly and they both express how much they missed each other. By the end of the episode, they kiss before he drives her into the airport, establishing the start of their long-distance relationship. In the finale of the series Randy reveals he has plans to become police chief of Summit, NJ and move in with Sharona.

Expandable timeline of Sharona and Randy's relationship:

Season One

In "Mr. Monk and the Candidate," Sharona bitterly asks Randy, "What is that, your tough look?"
In "Mr. Monk and the Psychic," Sharona says "I prefer to take care of business first," while talking to Captain Stottlemeyer. Randy mutters, "Bet that's not the first time you've said that," and Sharona snaps, "Bite me." The two chat by a table at the memorial service about Monk; Randy, slightly jealous of Monk, is criticizing his quirks while Sharona defends Monk. As part of a trap for the killer, they have to hold hands near the end of the episode, but neither seem affected or embarrassed; their hands aren't even fully shown together.
In "Mr. Monk and the Billionaire Mugger," Sharona, with Monk, brings an invoice to Randy directly since Monk is holding out on paying her and she needs money. He comments, "A little short, huh?" to which Sharona swiftly replies, "Yeah? So are you."
In "Mr. Monk and the Other Woman," while at a crime scene with Sharona and Monk, Randy says, "Can I ask you a question? Why are you even here?"
In "Mr. Monk and the Marathon Man," Sharona mutters, "Like you know," when Randy suggests that leaving toenails halfway painted is "the style now".
In "Mr. Monk and the Red-headed Stranger," Randy informs Sharona and Monk that he's in charge considering that the captain broke his arm. Sharona, knowing Randy, sighs and says, "Oh, my God." Randy sarcastically responds with "I'm so glad you're here!"

Season Two

In "Mr. Monk Goes to Mexico," while Sharona and the real Randy don't interact for much of the episode, the Mexican lieutenant who is clearly styled after him seems to show some interest in her, though not in the style Randy does starting a few episodes later.
In "Mr. Monk Goes to the Circus," Randy, annoyed by an enthusiastic officer who keeps spouting facts about Monk, is pretending to have never heard of him. The officer refers to Sharona as "pretty hot, huh?" and Randy replies with "You think so?"
In "Mr. Monk Goes to the Theater," while rushing over to an unconscious culprit, Randy stops to ask Sharona if she's okay.
In "Mr. Monk and the Sleeping Suspect," the two briefly flirt when Monk arrives at the crime scene. Randy continues to stare at Sharona for a few seconds whenever she stands next to him. Later in the episode, she teases him about missing her when she leaves for New Jersey, to which he awkwardly admits he would, "maybe a little."
In "Mr. Monk Meets the Playboy," Randy tries to impress Sharona by finding and burning a set of photos she’d been trying to hide. She stays silent for a minute before asking, "Did you look at them?" Randy responds by giving a noncommittal shrug and walking away awkwardly.
In "Mr. Monk and the 12th Man," Sharona has a new boyfriend: Kenny Shale, the deputy mayor. Randy brings it up at a crime scene and teases her the way she usually teases him, continuing to do this for most of the episode.
In "Mr. Monk and the Paperboy," Randy ends up in a conversation with Sharona, Kevin Dorfman, and his new girlfriend Vicki. He and Sharona make eye contact and grin once while Kevin is speaking. Later, when Sharona tries to hand Monk a wipe and he instead takes a dirty rag, Randy takes her hand and pulls the wipes away, which she doesn't acknowledge. At Monk's apartment, Sharona finds a personal ad Randy had put out reading "Man with a badge in hot pursuit of romance. I'm 32, fit, sexy, ambitious with a dynamite sense of humor. Looking for a petite blonde, no-nonsense attitude, kids okay." This is obviously directed at Sharona, who reads it aloud and confronts him. She mentions it again later and they look at each other briefly. Both times Randy denies the ad was meant for Sharona.
In "Mr. Monk and the Three Pies," Randy, while handing a check to Sharona, jokingly pulls it away before giving it to her — Sharona is unamused. Later, when she has to dig through a pie to find a bullet, Randy walks over to her and say, "You know, this is one of my fantasies. Except it's not a pie...and you're not in it." Sharona replies exasperatedly with "Will you shut up?" (Despite his claims, there is a very good chance that Sharona is in a number of Randy's fantasies.)
In "Mr. Monk and the T.V. Star," Randy notices Sharona is talking to Brad Terry from across the room and watches her for a while until she looks up, at which point he tries to look like he was reviewing notes all along. Later, at a party, he asks her to dance, but she turns him down, saying, "I'm not much of a dancer." She quickly goes to dance with Brad, however, and leaves him alone.
In "Mr. Monk and the Missing Granny," she teases him briefly about his allergy to cats, and then later about him being left in the captain's office while Stottlemeyer and Monk interrogate someone. At the end of the episode, Randy’s allergy has solved the case. Sharona smiles at him and congratulates him for it.
In "Mr. Monk Gets Married," Randy's mother has married a mysterious man after two dates, and he calls Monk and Sharona in to investigate. "I love you guys," he tells them drunkenly on their way out, to which Sharona nods and says, "Okay." She makes several comments to Monk that she feels sorry for Randy or that they have to do something since he's depending on them. At the end of the episode, she teases him that he can't even get his own mother to go home with him.

Season Three

In "Mr. Monk Takes Manhattan," Randy offers to share a hotel room with Sharona; however, she dismisses it quickly by scoffing and saying, "In your dreams." Later, he stutters when introducing her.

In “Mr. Monk and the Panic Room," Sharona believes a chimpanzee accused of murder is innocent and takes it to a kitchen to feed it. Randy immediately offers to come with her, to which she doubtfully asks why. He freezes for a second before giving an excuse. Sharona later teases him about a theory of his.
In "Mr. Monk and the Blackout," Randy and Stottlemeyer rush into Monk's apartment during a blackout. Randy immediately yells "Sharona, you okay?" into the darkness.
In "Mr. Monk Gets Fired," Randy is impressed when Sharona tackles the commissioner for a piece of evidence.
In "Mr. Monk Meets the Godfather," Randy spends the entire episode trying to get Sharona to not date Fat Tony. He even says at one point that he knows why she’s attracted to Tony: he’s dangerous, and goes on to add, "Some people think I'm dangerous." Sharona, amused, dismisses this easily. At the end of the episode, he finally proves that Tony is a bad person, and asks if this means that she won’t tease him as much. Sharona replies, smiling, with, "No chance of that," and walks away.
In "Mr. Monk and the Girl Who Cried Wolf," he brings her coffee after she supposedly sees a body. He also stops to ask if she’s okay before when they arrive at the culprit’s house. At the end of the episode he compliments a title of one of her stories, which is followed by a slightly awkward silence.
In "Mr. Monk and the Employee of the Month," a running joke throughout the episode is Randy's girlfriend, a wallet model named Crystal Smith. Sharona briefly teases him about Crystal being imaginary at the beginning of the episode and offers sardonically to come with as he takes a statement from someone so he can "tell her all about Crystal, the famous wallet model." She also notices he's wearing new cologne, which he claims was given to him by Crystal. At the end of the episode, Crystal is revealed to actually exist — yet Sharona barely misses seeing her, and, still skeptical, walks off.
In "Mr. Monk and the Red Herring," Sharona has moved to New Jersey with her ex-husband Trevor. Stottlemeyer mentions this in a conversation with Natalie Teeger, and Randy visibly reacts by rolling his eyes and sighing. He forces a smile when Stottlemeyer glances at him. Obviously still touchy about the Sharona situation, he asks Natalie bluntly if she has drugs in her home during their interrogation.

Season Six

In "Mr. Monk Is on the Run: Part 2," Randy brings a bouquet of flowers that were on Natalie's doorstep in to her. He begins to tell her they were out front, but pauses for a second mid-sentence upon seeing the card. The flowers are from Sharona, she and Benjy are flying in for Monk’s funeral. Randy is obviously affected by the idea of this. It's also implied that he knew before he saw the card, which indicates Randy and Sharona are still in contact or at least have been during the recent events involving Monk's "death."

Season Eight

In "Mr. Monk and Sharona," Sharona returns to San Francisco for legal issues regarding an uncle’s death. She stops in to see Stottlemeyer first, but Randy comes into the room once he’s told Sharona is there, awkwardly asking, "Is she here? There she is. She is...here." They hug briefly and grip each other’s arms. Sharona tells Randy it’s great to see him, which he doubts considering their earlier relationship in which she constantly teased him. She asks, "Oh, my God, was I awful?" and he replies quickly with "No, you were...Truth is, I missed it." When Natalie comes in, he acknowledges her without looking away from Sharona, and evidently has completely forgotten that he got a rap sheet for Monk under the circ*mstances. Later in the episode, Sharona interrupts him at work to talk to him about the case, saying how she remembered always feeling good after talking to him. Randy is affected by this and lets her rant to him. She finishes by saying that her and Natalie have been fighting, but she knows Monk likes her better. Randy asks how she can tell, and she responds with "A woman always knows...who likes who." They both look at each other as the elevator door closes. At the very end of the episode, it is revealed that they have gotten together officially, as Randy is Sharona’s ride to the airport. Much to Monk and Natalie’s surprise, they share a quick kiss as he helps her into the car.
In "Mr. Monk and the End: Part 1," Natalie finds plane tickets to Newark in Randy's pocket, most likely to visit Sharona, but he dismisses them as personal and something they can't talk about at the crime scene. Later, he accidentally comments "I'm gonna miss all this," while waiting for a suspect with Stottlemeyer.
In "Mr. Monk and the End: Part 2," Randy is shown updating Sharona on Monk's condition over the phone. He ends the call with "I love you," and when Stottlemeyer questions him, claims he was talking to the deputy commissioner. Later, while frantically driving to find Monk, he admits to selling his siren as well as having a yard sale. Finally, Stottlemeyer finds a letter he'd been holding on to, which says that Randy is leaving the SFPD to become police chief of Summit, NJ. When Stottlemeyer asks why, both Natalie and Monk smile and Natalie says, "I think I know the answer to that," teasingly, leading Stottlemeyer to guess Sharona. He says he always kinda knew, looking back, and that the two of them together was perfect. Randy moves into his new office by the end of the episode, with a picture of Sharona as the first thing on his desk.
In "Mr. Monk's Last Case," Sharona does not appear, but Randy visits from New Jersey, where he's earned the title of Sheriff. He confirms Sharona and him are married happily.

Trevor Howe[]

Trevor is Sharona's ex-husband, whom she was married to for a period of time before the show started. Sharona regrets marrying him and constantly remarks she didn't know why she ever did. During their marriage, Trevor was unfaithful, drank, and gambled. Even so, she worries often that Benjy needs his father. In the episode "Mr. Monk and the Sleeping Suspect," Trevor shows up during Benjy's birthday party, hoping to convince Sharona to move back to New Jersey with him. She says to Monk she believes he's really changed this time--he's stopped drinking, found a job, claiming to be ready to have a family. Sharona eventually gives in, but it isn't long before she finds out he was only trying to take advantage of her again. He visits again in "Mr. Monk and the Girl Who Cried Wolf," and Sharona is a little less hostile toward him, which comes into play only four episodes later when suddenly they've reconciled and she leaves for New Jersey with him and Benjy.

Sharona, Trevor, and Benjy live in New Jersey for several more seasons until Sharona returns to San Francisco and informs Monk they've split up for good. It's unclear when or how.

The novel Mr. Monk and the Two Assistants, published during Sharona's long absence from the TV series and later rendered non-canon by her return appearances, significantly expands upon Sharona and Trevor's relationship.

Friends[]

Adrian Monk[]

Throughout the series, Sharona usually takes advantage of Monk’s OCD and complains about his quirks, often to the point where it seems like she really doesn't care about him.

However, when it really matters, Sharona has always been there for him and helped him through what he needs to be helped through. In ”Mr. Monk and Sharona,” she admits to Natalie that taking care of him was the best job she ever had. She thinks she might have been too hard on him, but Natalie insists she got him through everything after Trudy died.

Natalie Teeger[]

Natalie and Sharona didn't officially meet until her season eight appearance, "Mr. Monk and Sharona." Before this, Natalie had obviously heard a number of very good things about Sharona, and the two immediately bonded over Monk and what they'd each had to deal with in their job. When Natalie first started as Monk's assistant, she demanded to be treated better than Monk had treated Sharona - once "waging war" against him in "Mr. Monk vs. the Cobra," refusing to help him unless he paid her expenses. The issue of money resurfaces in "Mr. Monk and Sharona," where Natalie finds out she was still being paid less that Sharona had been, and their differences quickly come into play. Despite the immediate connection Natalie and Sharona had, they were still very different people, and argued for most of the episode, bickering whenever they got the chance. After a particularly large argument that got both the Captain and Randy involved, Monk walked out of the room unnoticed, hailed a cab, and told the driver to go as far as he could. Natalie and Sharona ended up bonding as Sharona admits taking care of Monk was the best job she ever had, and she feels like she had been too hard on him. Natalie tells Sharona that Monk needed her to be hard on him, reassuring her that she did the hard part. "You were here right after Trudy when he couldn't even get out of bed," Natalie says. "You got him here. You got him to me."

Leland Stottlemeyer[]

Sharona and Stottlemeyer's relationship was barely explored in the few seasons she had. Both Randy and Stottlemeyer were doubtful of Monk's abilities at first, Randy displaying a clear dislike for Sharona and him. Stottlemeyer, though not as jealous, perhaps, as Randy, still wasn't particularly fond of them at first. Eventually it was clear they were close friends, considering how much they'd been through. Stottlemeyer tried once to take advantage of Sharona's relationship with Kenny Shale, but was caught by Sharona, who pointed out that he'd called Kenny a weasel three weeks ago. In "Mr. Monk and Sharona," they embrace upon meeting again and he says to Monk that he "loves Sharona" (platonically, of course).