His attention to detail and his Zen/Sherlock Holmes like demeanor enables him to read people and the environment, to see what others do not. Monk’s talisman is a set of keys that belonged to his wife’s car. He holds them close until he can discover the true facts behind her death. Monk occasionally will play his clarinet at the foot of his wife’s grave. Monk celebrates August 8th as an anniversary. It was the first time he met Trudy. Her favorite meal was Chicken Cacciatore. Adrian regularly visits his psychiatrist Dr. Charles Kroger on Monday, Friday and every other Wednesday.

When the San Francisco Police Department gets stumped on a case, they hire Monk as a consultant. Monk's liaisons with the force are Captain Leland Stottlemeyer, Monk's former boss (who had to fire Monk) and his chipper "Boy Friday" assistant, Lieutenant Randall Disher.

Monk’s sidekick and "Girl Friday" is a practical nurse named Sharona Fleming who monitors Monk's progress and helps him cope with stressful situations. For instance, when Monk walks down the street, he will compulsively begin to touch and count each and every parking meter he passes. And meal time has a strict order: Tuesday is always chicken pot pie night. Effectively, Sharona plays Dr. Watson to Monk's dysfunctional Sherlock Holmes.

Besides having to contend with Monk's idiosyncrasies, occasionally Sharona has to survive a visit from Ambrose Monk, Adrian's older brother who still lives in the same house at 1740 Oak View in which both he and Adrian grew up more than thirty years ago. Ambrose,  an instructional manual writer, who said "I am as God made me" has issues, among them being a pack rat and an agoraphobic. Ambrose blames himself for his father leaving their home and he waits patiently for his return. The kids on the block say of Ambrose "That's where the special man lives."

After Sharona left town to remarry her ex-husband, Monk hired Natalie Jane Teeger, a widowed bartender with an 11 year-old daughter as his new assistant. Although not a nurse, Natalie has the needed patience and compassion to be Monk's assistance.  Natalie comes from a wealthy family (Davenports) but is estranged from her parents because they did not support her marriage to her husband, Mitch.. The Davenports earned their fortune with toothpaste and mouthwash.

Adrian graduated in 1981 from University of Berkeley in California. He shared dormitory room #303 with his roommate who used a tie on the doorknob as a "do not enter/disturb" signal.

It was at college that Arian met his future wife, Trudy while he worked in the library. She came in one day (Tuesday at 4:30) looking for a book by Alexander Pope (Volume 2). And although that section of the library was being reorganized and all the books were stacked in large piles on the tables, Adrian's photographic memory enabled him to find the exact book that Trudy needed. Bedazzled by Trudy, Monk summoned the courage to call her three weeks later. Trudy was dating some one else at the time, but she soon fell in love with Adrian.

"I love you. Well, were in big trouble. because I love you too." - Adrian and Trudy, sitting on a bench at college.

Adrian's nickname in college was "Captain Cool" because he was obsessed with keeping his dormitory refrigerator clean and defrosted. Adrian was so fastidious that whenever he saw a weed growing anywhere on campus, he took the time to pluck it. In later years, Adrian would even wander through a supermarket and pull all of the expired products off the shelves and wheel them up to the check out counter.

When Adrian attended his 25th college reunion, we learned of Adrian's "superpower" (per Natalie). Namely, if someone used his back as a surface to write a note, Adrian could discern the letters and numbers as a person pressed pen to paper. This is how Adrian got his wife's college phone number when a rival suitor used Adrian's back to write down Trudy's number.