Adrian Monk/Relationships

The relationships of Adrian Monk, the protagonist of the TV series of the same name

Love Interests

Trudy Monk

Adrian with his wife, Trudy Monk.

Trudy was Adrian's late wife. The two first met at college long after her affair with her professor in 1983. According to Monk, Trudy had wrinkles in her eyes because he would often make her laugh. In the 1980s, Adrian and Trudy married, with a beautiful wedding ceremony. According to Adrian, Trudy once asked her husband if he considered having children with him. However, he always told her that they always had the time in the world to be parents, a decision he would soon regret in the future. Unfortunately, Trudy was killed in a car bombing and Monk heard the news from a call Stottlemeyer got. Adrian never truly got over her death, with some of his friends trying (and failing) to bring him back. As a result of Trudy's death, he lost his shield/badge and suffered from depression and OCD.

Despite this, Adrian had fond memories of his wife and vowed to solve her case, even if he had to take it to the grave. Additionally, whenever someone insulted her or her death, Adrian's mild manner disappeared and he got angry, even on the verge of hurting someone.

In 2009, Monk discovered the final Christmas gift from Trudy, which led him to the painful realization that she had been murdered on the orders of Judge Ethan Rickover. Monk confronted Rickover, asserting his knowledge of the judge's involvement in Trudy's death, despite lacking concrete evidence. As Monk delved deeper, he understood the reason behind Rickover's reluctance to leave his long-time residence. This prompted Monk to confront Rickover once more in his yard upon his return home, where he compelled Rickover at gunpoint to unearth the remains of Wendy Stroud. The body was ultimately recovered in the presence of both Monk and law enforcement, leading to Rickover's confession regarding the murders of Wendy Stroud and Trudy Monk. Choosing not to take Rickover's life, Monk (who was weakened from the poisoning) discarded the weapon, which Rickover then seized, placing it against his head and uttering, "You take care of her!" before taking his own life.

As the sole individual aware of Trudy's surviving child, Rickover's cryptic message went unrecognized until Monk stumbled upon an article revealing that Wendy Stroud had discovered a baby girl in 1983. This revelation led Monk to understand that Rickover had been hinting that Molly was still alive sometime after he and Natalie were healed from the poisoning. He sees much of Molly in Trudy and allows him to move on from Trudy's death and get over most of his phobias.

Sherry Judd (Ex-Crush/Classmate)

It was revealed in Mr. Monk and Little Monk that Monk had a crush on a girl named Sherry Judd. He was later reunited with her three decades when she hired him to investigate the murder of her housekeeper. He thought about asking her out, with even Captain Stottlemeyer and Natalie encouraging him to do so but Monk couldn't because Sherry still had romantic feelings for an art restoration worker and he was forced to back off.

Monica Waters (Ex-Crush)

In "Mr. Monk and the Other Woman," Adrian falls in love with another woman Monica Waters due to her similar appearance and personality to Trudy as well as her OCD traits. However, she has more control of her disability and it turned out she has a husband who was suffering from schizophrenia. When Stottlemeyer insisted that she was a suspect and he saw Adrian was in love with her, he had to remind him that Monica wasn't Trudy. At the end of the episode, Monica decided to go be with her husband but not before Monica thanked Adrian for helping her realize this.

Michelle Rivera (Date)

In Season 3, Adrian went on a date with Michelle Rivera, a PR worker from an electric company; but that ended in disaster when Adrian discovered the restaurant was on the top of the building. She still kissed him on the cheek and told Adrian she would like to again but this time at a restaurant on the first floor.

Leyla Zlatavich (Former Love Interest)

In Mr. Monk Falls in Love, Adrian becomes smitten with Leyla Zlatavich, who was also suspected of being the killer, and yet another woman who looks similar to Trudy. His seriousness about it was so strong that Adrian took off his wedding ring for the first time in 11 years and danced with her in her apartment.

However, due to losing himself, Monk decided he couldn't be there and that he had to leave. Stottlemeyer and Randy had come to Leyla's apartment, where are confessed to the murderer to protect her mother. Once Adrian told Mrs. Zlatavich what was happening, she confessed so her daughter wouldn't get charged with something she didn't do.

Ellen Morse (Ex-girlfriend)

Ellen Morse was Adrian's love interest in Mr. Monk Gets Even.

Family

In "Mr Monk is On The Air", he mentions having an aunt named Clara and an unnamed cousin, both of who are seen in video footage from a home video that his brother Ambrose made and gave to Adrian.

In Mr Monk and The Bully, he mentions having a grandmother who gifted him off camera. However the camera is an old model Monk probably got it from his grandmother when he was a child.

Mrs. Monk

Mrs. Monk was Adrian's mother; his exact relationship with her was unknown, but she was cut off from her children especially after her husband abandoned them. Even though his mother was emotionally distant from her sons, she still provided for Ambrose and Adrian. According to Ambrose, their mother never laughed again and it was actually Adrian who kept the family going.

Jack Monk Sr.

Jack, Adrian's father, disappeared in 1967 when Adrian was only eight years old. Since Jack abandoned his family, Adrian developed resentment and anger towards him. This sense of abandonment, along with the murder of Trudy, became significant subjects for Adrian to explore over the years. Despite all the time that had passed, Adrian always doubted that Jack would return to him and his brother, Ambrose. This skepticism was one of the reasons the brothers struggled to get along. Adrian could never understand why Ambrose had faith in their father or why he never touched anything in Jack's office.

The two were reunited on December 25th, 2006 when Monk's father was arrested for running a red light and resisting police officers. During the journey, Adrian and Jack made amends by solving the murder together which was Jack's boss. At the end of the episode, Jack buys Adrian a bike and teaches him how to ride it after they solve the case

Ambrose Monk

Ambrose was Adrian's older brother by 2 years but he suffers from agoraphobia (great fear of going outside of home). Over all the years Adrian always has his doubts that Jack would return to him and Ambrose, which was one of the reasons he and his brother didn't get along. Adrian couldn't understand why Ambrose had faith in their father, why he never touched a single thing in Jack's office, or why Ambrose didn't attend Trudy's funeral because of his guilt about his sister-in-law's death. Over the next seven years, the brothers didn't speak to each other until Ambrose contacted Adrian about a suspected murder of Ambrose's friend and next-door neighbor.

Later just as Ambrose tries to get Adrian to stay for dinner, Ambrose told his brother that he loves him. Monk stopped and precedes to yell at Ambrose for not coming to Trudy's funeral because of his agoraphobia. However, Ambrose broke down crying that it was his fault Trudy was in the parking garage the night she died because she was running an errand for him. However, Adrian immediately comforted his brother and insisted it wasn't his fault. Later at Sharona's house, Adrian reenacted the night that Rita van Ranken was shot by her husband. He and Sharona recreate the night of the murder in their respective kitchens, and both come to the same realization: the shell casing didn't land in the pie, but in the bag of flour - the bag that was now back at Ambrose's house. Adrian and Sharona rush to Tewkesbury, where they see the house on fire. Monk quickly rushed into the house and forced his brother to leave to save himself by encouraging him to get out of the house for Trudy's sake. The Monk Brothers were able to reconcile at last and went to Trudy's grave before they walked out and decided to have lunch together at home.

It was currently unknown if Ambrose was aware of his brother finally discovering that Ethan Rickover murdered Trudy or the fact that his brother recently reunited with his long-lost stepdaughter.

Molly Evans

When viewing Trudy's last Christmas present, he found it difficult that Trudy had an affair with her professor and that she "lost" the baby. However, at the time, Trudy (and Adrian) both assumed the child had died. It was not until Adrian confronted Ethan Rickover, the man who killed Trudy that he confronted Rickover for killing three people for nothing. Before Rickover’s death, he told Monk to "take care of her," which he didn't understand at first. After finding a newspaper that a newborn girl was found in the park by a nurse in 1981, Adrian figured out that Rickover was leading him to Molly and trying to go for compensation for killing Molly's mother.

He managed to find out that Trudy's daughter survived childbirth and did not die as Trudy believed. With help from Stottlemeyer, Adrian found a now 27-year-old Molly Evans, who Adrian immediately connected to, and eventually paternal affection for his step-daughter.

Though Adrian began the story as a broken man with no family and various problems, meeting Molly finally allowed him to not only heal but have a family again.

It was shown in Mr. Monk's Last Movie that Molly and Monk may not be biologically related but they do have a strong father-daughter bond. She moved in with Adrian following the COVID-19 pandemic to look after him after he relapsed from his OCD. However, Adrian wants Molly to live her life and doesn't want her worrying about him constantly due to his desire to even commit suicide. However after Molly's fiancé was murdered, Monk made it personal to find Griffin's killer after Molly hires him to find out the truth. Near the end of the film, Molly stops Monk from risking his life because losing him would destroy her.

Griffin

Griffin was Molly's fiancé and therefore would've become Adrian's son-in-law if he hadn't been murdered. In Mr. Monk's Last Case movie, Monk spends most of it thinking about committing suicide and whoever would have wanted to kill Griffin. This fuels his anger towards Rick Eden, even to the point of trying to attack him until Stottlemeyer restrained him. At the end of the movie just as Monk considered taking his own life, Griffin was one of the spirits who showed himself to Monk. The ghosts showed gratitude towards Adrian because he helped solve his murder. It also convinced Adrian that living meant he should continue to solve other people's.

Friends

Leland Stottlemeyer

Best Friend (1990-present)

Leland Stottlemeyer was the former Captain of the San Francisco Police Department and Adrian Monk's best friend and former partner. They go way back since Adrian's rookie days at the San Francisco Police Department. After going through with three partners, Adrian immediately connected to Stottlemeyer, who was always supervising Adrian as his watch officer. They were also familiar with their respective wives, Trudy and Karen (who was married to Leland at the time), and seemed to become close with each other's families.

Since their partnership began, the two became very close, almost like brothers. However, after Trudy's death, Stottlemeyer noticed that Monk had fallen into a deep sadness, which caused them to grow distant from each other. In Season 1's episode "Mr. Monk and the Candidate," it was suggested that Stottlemeyer and Monk had not seen each other in three years. Throughout most of the first and part of the second season, Leland often felt frustrated when he had to contact Adrian to come to a crime scene. He believed Monk wasn't ready to return to work and felt somewhat jealous of Monk's talents. However, during Season 2, the bond between the two men began to improve. Stottlemeyer became less irritated with Adrian and their relationship grew stronger.

A turning point in Stottlemeyer and Monk's friendship was in the episode "Mr. Monk and the Captain's Wife." Stottlemeyer's wife, Karen was in a car accident courtesy of her crashing into a repo truck after the driver had been shot dead by Evan Coker shooting a repo truck driver. Throughout this episode, Monk becomes increasingly protective of Stottlemeyer, worrying about his emotional state right now, which was where Adrian has been in his life since Trudy died. Later, Stottlemeyer tells Monk he finally understands why he can never move on from Trudy and that he should never let go of the watch she gave him. Afterwards, Monk and Stottlemeyer become closer again.

In Season 3, "Mr. Monk Takes his Medicine," Adrian was very concerned when Stottlemeyer was shot and quickly ran to the scene with Sharona even ending his therapy session with Dr. Kroger. After failing to stop the suspect who shot Stottlemeyer from getting away, Adrian felt guilty so he decided to take the medication that Dr. Kroger recommended he take to help with his OCD; however, the drugs turned Adrian from a mild-mannered, observant, into a carefree, self-absorbed narcissist. After he stopped taking the meds, Adrian apologized to Sharona at the victim's apartment, where they learned through the victim's suicide note about a robbery. On the drive there, Stottlemeyer (over the phone), asked if Monk was back. When Sharona turned the phone over so Leland could hear Adrian complain about driving through a red light, Stottlemeyer realized Monk was not under the meds and "welcomed" him back.

Stottlemeyer may still experience frustration with Monk's idiosyncrasies, yet he remains steadfast in his support for him. He now initiates contact with Adrian without needing a prompt, demonstrating a deep sense of protectiveness whenever Monk faces danger. Additionally, Stottlemeyer ensures that Monk remains focused during investigations, often adapting the environment to suit Monk's needs and serving as his rational counterpart. Their mutual respect was evident, as they exhibited a protective and nurturing demeanor towards each other. In grave situations, they occasionally address one another by their first names (Mr. Monk and the Other Woman, Mr. Monk Bumps His Head, etc.)

Sharona Fleming

Sharona and Monk met a year after Adrian's wife, Trudy was killed in a car bomb. She was the first one who helped coax Monk out of a catatonic state and get him to leave the house. Monk credits her as the one who saved his life and recalled that Sharona was hired by Leland Stottlemeyer. In the episodes she appears in, Sharona is the only one who keeps Adrian on track abs helps him control his OCD . However she does lose her temper with him when her paycheck bounced or when Adrian scares away her crushes.

Additionally, Sharona realizes how brilliant Monk is and knows when he solves the case when she sees him smiling ("Mr. Monk and the Billionaire Mugger" and "Mr. Monk and the Playboy.") However, there are times when Sharona disagrees with him, as she refused to believe that Dolly wasn't psychic in "Mr. Monk and the Psychic." She also does not believe Monk's theories that one of her favorite actors was the murderer of the actor's ex-wife until Sharona sees the determination in Adrian's eyes. Instead of gloating, Adrian gives her an apologetic look before continuing. Despite their misgivings, Sharona and Adrian still care for one another and it was often shown that Monk would do anything for Sharona.

Monk was often the one who went to save her or help her (Mr. Monk and the Candidate, Mr. Monk and the Earthquake). When a sleazy playboy, Dexter, blackmailed Adrian to step away from the Elliott D'Souza case, threatening to publish incriminating pictures of Sharona in his magazine, Adrian reluctantly agreed to stop investigating in fear of what this impact would on Sharona and her 11-year-old son. However, when Sharona found out about this, she told Monk to nail him no more, which was exactly what he had done.

It was also shown that Sharona will mother Adrian and treat him like a child at times, as seen in Mr. Monk and the Other Woman when he asks for permission to sleep at Monica Waters' house and later Monk chastises Sharona that he's not a child when she advised against it. However, it was sometimes vice versa.

In "Mr. Monk and the Red-headed Stranger," Sharona tells Adrian that he's not her mother when he tries to interfere in her relationship with Justin. In the end, Adrian proves to be right when Sharona learns that Justin was the streaker in the Jason Cross murder investigation.

In "Mr. Monk and the Sleeping Suspect," Sharona follows along with Monk's theories that the man in the coma, Brian Babbage, sent bombs in the mail to kill his siblings Ricky and Amanda. When Sharona's ex-husband Trevor shows up at Benji's 11th birthday party in the episode, Sharona thinks of leaving for New Jersey to be with Trevor so Benjy can grow up with his father. Adrian was very upset and probably jealous of Trevor and the situation at hand, even suspecting Trevor of being dishonest and coming to the house for ulterior motives. However, when Sharona came to pick him up from a house, she announced to Adrian she wasn't leaving for New Jersey because Monk was right about her husband just coming there for his selfish desires.

In "Mr. Monk and the 12th Man," Sharona gains much attention from everybody in the town when she starts dating the deputy mayor, earning Adrian's jealousy and annoyance. However, after Sharona breaks up with her boyfriend, Kenny resigns as deputy mayor, and Sharona is treated just like every other citizen again when a police officer does not let her off on a parking ticket.

Eventually, Sharona moves back to New Jersey after reconciling with Trevor, which has a completely bad impact on Adrian until he meets Natalie Teeger.

Randy Disher

Disher was a former lieutenant of the San Francisco Police Department and a good friend of Adrian Monk's over the years. During most of Season 1 and a part of Season 2, Randy was strongly against Adrian coming to crime scenes. Despite initially being jealous of Monk and calling him the "defective detective," Randy couldn't help but be awesome by Adrian's intuition. However, like Captain Stottlemeyer, Randy grew to respect and admire Adrian's skills as a detective. Adrian would also refer to Randy as "Lieutenant Disher" but later call him by just his first name.

In "Mr Monk Goes to a Farm," Monk helps Randy investigate his uncle Howard's death but has a strong aversion to being at the Disher farm. Since being there, Adrian sees that Randy is bad at taking care of it. When he sees that his friend has been feeling unconfident lately, Adrian goes into Randy's bedroom and whispers the "here's what happened" story to Disher so he can review it in the morning and regain his confidence.

Later during a 4 year hiring freeze, both Randy and Stottlemeyer were shocked that Adrian was thinking about quitting to be a butler instead. As a result, Stottlemeyer threatened the police commissioner that he would quit if Adrian wasn't excluded from the hiring freeze. According to Randy, he too was close to quitting.

In the series finale, Randy and Leland frantically searched for Monk when he went to confront Ethan Rickover for his role in Trudy's death. To their relief, Monk never went through with killing Rickover because it's something Trudy would not have wanted. As soon as Adrian lost his grip on the pistol, Stottlemeyer and Randy drew out his gun when he saw Rickover pick up the pistol Monk dropped, clearly ready to defend A weakened Adrian.

Julie Teeger

Much like Benjy, Julie played the role of surrogate child to Monk, who has no children of her own. She was rarely annoyed with his quirks and finds them endearing. Natalie revealed that Julie looks up to Monk as a father figure, which he neither confirms nor denies. Julie considered him to be the bravest man she had ever known, other than her father, ever since he saved her fish's life.

In "Mr. Monk Goes to a Wedding," when he saw Theresa Scott threatening to kill Natalie's brother, Jonathan with a knife, Adrian's first instinct was to pull Julie away. Later, when Julie was temporarily a model for extremist fashion designer Julian Hodge, Adrian immediately realized that he was the one who murdered Clea Vance and Natasia (the victims in the episode). He feared Julie could be in safer, so he frantically informed Natalie, who immediately rushed her daughter out of the building when they raised Hodge was dangerous. Monk later helped Natalie find Julie when she disobeyed her mother and snuck out.

In season 6, Julie begins her first romantic relationship but ultimately breaks up with him after being asked out by the most popular guy in school. Even though he was uncomfortable about it at first, Monk ended up giving Julie helpful advice on relationships. He told her the story of how he met Trudy and Julie realized she still could find "her Trudy."

In "Mr. Monk and the Three Julies," Adrian became protective of Julie when two Julie Teegers were recently murdered: the first at home and the second at a supposed hit-and-run accident. The first two victims had been false alarms, with Monk sighing and relief when Natalie told him that it was not Julie who was hurt. After catching Matthew Teeger, Monk came into the room Natalie and Julie were staying in at the precinct and said it was all over. After that, Julie asked her mother if she could still take her driver's test but Natalie was very reluctant to let her daughter do it. Instead, Natalie said that if Monk said it was okay, then Julie could go. Desperate to get her driver's license, Adrian tried to pass off the "parenting Julie" to Stottlemeyer, who wanted to no part of the argument.

Teeger, the suspected serial killer, saw Julie's name in her binder and Monk got defensive of her. After Matt was taken away, Julie j continued to beg Adrian to let her go to her driver's test. The man looked into Julie's eyes and found it impossible to just say no to her, just like Natalie warned him about. He quickly agreed to her wanting to get her driver's license after a nearby police officer decided to drive Julie to her driver's Ed. Unfortunately, the suspect, Matthew Teeger, who had a strange obsession with his mother Juliet Teeger, escaped custody. However, Monk figured out Matthew was not the guy coming after Julie and quickly misdirected the sniper's gun, where it hit Stottlemeyer's car instead. After learning that Julie obtained her driver's license, Adrian asked Natalie how Julie passing the test would affect his role in the front seat.

It should also be worth noting that Adrian reluctantly accepts hugs from Julie but he never returns them due to fears of being touched. In "Mr. Monk and the End," Adrian learned he had a stepdaughter, Molly, and that his relationship with Benjy and Julie was finally about to pay off when he formed an instant father-daughter relationship with Molly.