Family[]
Adrian Monk[]
Ambrose's relationship with his brother was iffy, as they weren't especially close during their childhood and by 2004 neither had spoken to the other for at least seven years. Ambrose, who suffered from agoraphobia, stayed locked in their childhood home at all times, keeping all the mail he received in the hopes his father would return (which Adrian maintained would never happen).
When Trudy died, Ambrose blamed himself since she'd been out to pick up cough medicine for him--otherwise, he figured, she wouldn't have been in the parking garage that day. As a result of the guilt he felt, he never reached out to comfort his brother following her death nor responded to Adrian's many calls. As the years went by, Adrian decided to consider himself an only child and pretended his brother didn't exist, until Ambrose contacted him in "Mr. Monk and the Three Pies."
Ambrose reached out to his brother in 2004, hoping he could help investigate what he thought might be a murder. They awkwardly embraced upon meeting and Adrian promised to look into it, only to hurriedly leave with Sharona a few minutes later. To his dismay, though, he noticed several clues outside the house and was forced to look into it. Later, Ambrose tearfully confessed to Adrian that Trudy's death was, in his eyes, entirely his fault--and the reason he'd avoided talking to Adrian for years. Adrian forgave him. Later, Adrian realized Ambrose could be in danger after figuring out what had happened to his neighbor and rushed back to Tewkesbury to find his house in flames. He managed to drag Ambrose out of the burning house to everyone's shock--"for Trudy's sake," he'd implored Ambrose. Later, the two of them visited Trudy's grave together.
After the events of "Mr. Monk and the Three Pies," Adrian and Ambrose were on good terms again. Adrian visited again the next Halloween when Ambrose had been contacted by their father, but ended up investigating a poisoning and missed out on reuniting with him.
Jack Monk[]
When Ambrose was young, his father went out for Chinese food and never came back. Ambrose held on to the belief that his father would come back someday, while constantly blaming himself for why Jack left. For years, Ambrose stayed at their house, keeping all the mail and newspapers delivered to them, telling Adrian that their father would be back someday and he would be so grateful that Ambrose had stored all the mail he missed. Devoted to the idea of his father returning, Ambrose ignored Adrian's warning that he was gone for good. In "Mr. Monk Goes Home Again," Ambrose finally gets a call from Jack--he was in town on a business trip, and he was stopping by. Ecstatic, Ambrose reaches out to Adrian, and he brings Natalie and Julie with for Halloween. It's not long before Monk realizes a case he was working on earlier is connected to something that happened not too far from Ambrose's house, and by dinnertime, Ambrose's house is empty as they have all been swept up in the new murder mystery. When they all return, there's a note on the door reading: "Stopped by. Nobody home. Can't blame you. I wouldn't wait for me either. - Dad. P.S. Ambrose, I'm proud of you for getting out of the house." Ambrose is overjoyed that his father was proud of him.
Jack later reconciles with Adrian in the episode "Mr. Monk Meets His Dad," but Ambrose does not appear.
Friends[]
Sharona Fleming[]
Ambrose and Sharona met once, in the episode "Mr. Monk and the Three Pies." Their relationship, though not explored too much throughout the episode, was amicable. Sharona was certainly kinder to Ambrose than Adrian at first, and played a big part in the two reconciling in the first place. She tried helping with Ambrose's agoraphobia once, by taking his hand and attempting to lead him out the door. Ambrose wasn't able to make it, and Sharona told him, "Adrian's scared too, all the time. But he doesn't let that stop him." She implored Ambrose to ask himself what Adrian had that he didn't, and he quietly replied, "He has you," to which Sharona was silent.
Natalie Teeger[]
Ambrose and Natalie met in the episode "Mr. Monk Goes Home Again," about a year after Sharona left for New Jersey (which Natalie explains on the phone, as Ambrose hadn't heard about Monk's change in assistants yet). Ambrose is immediately attracted to her, and has a hard time letting go of her hand after he shakes it. After Ambrose is attacked by the man in the Frankenstein's monster mask, Natalie takes care of him, holding an ice pack against his head and resting her hand on his arm. He later takes Monk aside--at first only to the next room, but eventually all the way up in the attic--with a point of making sure Natalie can't hear them to ask if they were involved. Monk, taken aback, denies it. Ambrose proceeds to ask if Natalie was seeing anyone for "no reason."
When Julie wants to go trick-or-treating, Ambrose suggests Adrian take her so that Natalie could stay with him. While everybody else is out of the house, Natalie admires an old book filled with pictures of Ambrose and Adrian's childhood. Ambrose tells her his father leaving was his own fault, and Natalie says that's what Adrian always says about himself. A while later, everyone else is still out trick-or-treating and Ambrose and Natalie sit waiting on the sofa. Natalie rubs his arm to comfort him and he works up the nerve to ask her out. She lets him down gently, saying that it could get messy since she works for Adrian. She assures him that if she ever gets another job, she would consider it, which Ambrose takes as a "maybe."
It gets late enough for the idea that his father may not show up to seem real to Ambrose, who resorts to having a miniature breakdown. He cleans out his father's study, then proceeds to eat his remaining candy despite having carefully calculated how much he needed. Adrian realizes that one of the Neptune bars could have been poisoned, and they rush Ambrose to the hospital. Halfway there, he realizes the bar was expired and, overcome with relief, they all laugh. As they walk back up to the house, Natalie says Friday could work for their date, which Ambrose protests she doesn't have to follow through on since she thought he was dying. "I'll be here Friday," she tells him.
Ambrose and Natalie's relationship isn't mentioned again after this episode, nor is their date.