Wedding bells are ringing for Natalie's brother Jonathan. Needing a "buffer" to deal with her estranged parents, Natalie asks Randy along as her date, but soon has more to worry about when Randy is hit by a car. As clues pile up, the situation turns into a police investigation, and it appears that Jonathan's special day may not turn out to be so special after all.
This episode includes examples of the following tropes:
- Adult Fear: It's discovered midway through the episode that Teresa Scott is hiding a past as a black widow, putting Jonathan at risk from a serial killer on a day that is supposed to be joyous.
- Blackmail Backfire: The wedding photographer figured out Teresa's secret and blackmailed her over it. He found out the hard way why it's a dangerous thing to blackmail a murderess.
- Black Widow: Natalie's brother was about to marry a bride who had repeatedly killed her earlier husbands. According to Randy, who investigated her, she had at least three, not counting Jonathan Davenport.
- Body in a Breadbox: The investigating police find the missing photographer dead in a mud bath.
- Bridal Carry: Played for laughs; Stottlemeyer briefly carries Randy in his arms while rushing him to identify Teresa.
- Cannot Tell a Joke: Monk makes an excruciatingly painful attempt at stand-up comedy while stalling Teresa.
- Chekhov's Gun: Teresa calls Randy a sergeant. Randy was a sergeant when he was investigating a potential wedding murder six years ago, when she was also the bride.
- Dating What Daddy Hates: Natalie tells Randy how her family pressured her to date the right guys in high school. She responded by dating all the wrong guys.
- Full-Name Ultimatum: Downplayed; Peggy calls Natalie by her first and middle name when chastising her.
- Holding the Floor: Monk does a long-winded toast to hold Jonathan Davenport's Black Widow bride at bay until Stottlemeyer can bring Randy down to identify her.
- I Have Many Names: A third-person variation; Teresa Scott Davenport has gone by several different names over her years as a black widow. Randy lists a couple of them off when he identifies her.
- Irony: Natalie's parents already have a picture of Teresa (a black widow) up with their family photos and yet haven't put up Mitch's photo, even long after his death.
- Is That a Threat?: Teresa denies Monk's allegations but points out that if she was really a black widow, it would be foolish to get in her way. Monk responds by asking if she's threatening him.
- Meaningful Echo: Before meeting her parents, Natalie designates a "safe phrase", "What time is it?", that means Randy needs to get her out of there. A few minutes later, when Randy puts his foot in his mouth, he says, "What time is it?"
- Skewed Priorities: During the investigation, Natalie's mother takes Randy's bloodied pants because she doesn't like the shade of the tablecloths and wants to show the person in charge the shade she wants (crimson).
- Speak Now or Forever Hold Your Peace: Subverted; Stottlemeyer does find evidence that Teresa is bad news, but he does not arrive until after the officiant has already pronounced Jonathan and Teresa man and wife. The wedding goes off without objection; it's the reception where things go haywire.
- Spot the Thread: Teresa says her parents (and her uncle) died in 1995 on a Pan-Am flight, but Monk notes that airline had gone out of business four years before that.
- Terms of Endangerment: Teresa calls Mr. Davenport "dad" as she holds a knife to Jonathan's throat and demands the company airplane to escape in after she's outed as a black widow.