Relationships
During the series, Disher loses his entire life savings during a trip to Las Vegas in "Mr. Monk Goes to Vegas", which prompted Monk and Stottlemeyer to come to his rescue, using Monk's abilities to win the money back. He acts as Natalie Teeger's bodyguard in "Mr. Monk and the Election. He helps Monk find clues for the Trudy Monk case by traveling to New York with him in "Mr. Monk Takes Manhattan". Randy is shown to argue regularly with but not-so-secretly be attracted to Monk's first assistant, Sharona Fleming, and he maintains a friendly, professional behavior towards Natalie.
Throughout the series, Randy seems to always harbor crushes on Sharona and Natalie. As well, he wrote a personal ad fitting Sharona in "Mr. Monk and the Paperboy", which he unsuccessfully tries to hide from her. In the season 6 episode "Mr. Monk and the Bad Girlfriend", when Natalie tells Randy that she and Monk have news, he guesses that she wants to say she is in love with him, leaving Natalie in a dumbstruck state while Monk delivers their theory that Linda Fusco killed her former partner. Natalie is shown to be rather annoyed by Randy's theory that she is in love with him (bringing it up again when Monk asks Randy if he has any crazy theories about how to break Linda's alibi).
His lack of luck getting dates is so notorious that when he does land a girlfriend, in the episode "Mr. Monk and the Employee of the Month", no one believes him. Throughout that episode, he shows the cast a generic picture of a woman. Sharona confirms that it was included with his wallet. They dismiss Randy's claims that his girlfriend is a wallet model named Crystal Smith (when Randy mentions that her first name is Crystal to Sharona, she asks if Crystal's last name is "Glassware", referring to the box of Crystal Glassware in the loading dock). It is revealed to the viewers but not to the characters that Randy was telling the truth.
A few episodes later, in "Mr. Monk Gets Cabin Fever", he dates a Chinese woman named Hayley, who turns out to be part of a Triad hit crew sent to kill Monk.
In later seasons, Randy's success with women significantly increases. For instance, both in the season seven episode "Mr. Monk Falls in Love" and in the following "Mr. Monk's 100th Case", he's seen dating two different, attractive girls who seem to be really into him.
It is hinted at the end of "Mr. Monk and Sharona" that he may be dating Sharona, whom he eventually marries. In the series finale, Randy accepts a job as Chief of Police in her native New Jersey.
Read more about this topic: Randy Disher