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:
- Beware the Nice Ones: Natalie can put a serial killer in a painful hold if one is threatening her little brother.
- Big Sister Instinct: Natalie ends up taking down Teresa when the latter takes her brother hostage. She twists the latter's arm to get her to drop the knife, and pins her to the floor with her heels.
- Blackmail Backfire: Frank Ruttle, 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: One of the women at the resort find the missing photographer dead in a mud bath.
- Boulder Bludgeon: Theresa knocks out Frank with a rock from a bowl in the sap before pushing him into the mud.
- Bridal Carry: Played for laughs; Stottlemeyer briefly carries Randy in his arms while rushing him to identify Teresa, before giving up and loading him on a luggage cart.
- 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. Stottlemeyer gets him to the wedding to identify her.
- Continuity Snarl: Stottlemeyer claims he met his wife at a wedding, in "Mr. Monk And The Captain's Wife", he claimed they were childhood sweethearts. They could have grown apart and reacquainted at the wedding, however.
- Dating What Daddy Hates: Natalie tells Randy how her family pressured her to date the right guys in high school. She dated all the wrong guys.
- Disney Villain Death: Mr. Coolidge, one of Teresa's husbands, died when Teresa threw him off a balcony.
- Epic Fail: Monk drapes cellophane over a birthday cake for Disher in order to create a spittle shield when he blows out the candles. When Disher blows, it ends up setting the cake on fire.
- Failed a Spot Check: Monk mistakes a stripper for an actual police officer, asking him to go to a crime scene.
- A Father to His Men: Captain Stottlemeyer is protectively outraged when Randy gets targeted in a hit-and-run, insisting that it's his case even though it's out of his jurisdiction.
- Faux Affably Evil: Jonathan's bride is cute and friendly and has a record of marrying rich men and murdering them...as well as anyone else who gets in the way.
- Foreshadowing:
- When she’s asking about Disher’s condition, Teresa calls him “sergeant”. In the past, Randy’s former title was sergeant and the only way she knew that was because he worked on a previous case that focused on her.
- At the bachelorette party, Teresa says "I've been a bad girl". Turns out she has been, what with having killed four men and plans on killing another.
- Freeze-Frame Bonus: Randy still has a bushy mustache in the old newspaper clipping, which was first glimpsed when he showed his old ID way back in "Mr. Monk and the Earthquake".
- 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. It barely works.
- 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 who isn't even married to their son yet) up with their family photos and yet haven't put up Mitch's photo, even long after his death. After Teresa is arrested, Natalie's mother takes her picture down and puts up one of Mitch.
- 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.
- Let's Get Dangerous!: Natalie when Randy identifies her sister-in-law as a black widow. Stottlemeyer isn't close enough to rescue her brother from a knife at his throat, so Natalie ambushes Teresa by twisting her arm, making her drop the knife, and knocking her to the ground.
- 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 after their arrival, when Randy puts his foot in his mouth, he says, "What time is it?"
- Overly Long Gag: Monk trying to delay the newlyweds' departure is juxtaposed with Stottlemeyer trying to bring the injured Randy to the reception to identify Theresa, both of which take a very long time.
- Papa Wolf: When Teresa grabs a knife, Monk's first instinct is to pull Julie away from her.
- Prodigal Family: Natalie is forced to face her pushy parents, who are snobby and disrespectful to her husband's memory, because she's been invited to her brother's wedding. Predictably, the ceremony is disastrous even though she brings a plus one to act as a buffer.
- Relationship-Salvaging Disaster: Natalie saving her brother's life is what allows her to reconcile with her parents.
- Revealing Cover-Up: Monk and Stottlemeyer get involved because Theresa tried to run over Randy out of fear that he would recognize her as a potential Black Widow bride. Given that Randy was there as Natalie's plus-one, he may not have been in "work mode" enough to make the connection if the murder attempt hadn't convinced him something was going on. Monk and Stottlemeyer weren't even at the wedding before the hit-and-run.
- Running Over the Plot: Monk and Stottlemeyer get involved in the plot not because of the wedding photographer’s death, but because the killer tries to run over Disher in the parking lot. This becomes vital to the plot because the killer is a Black Widow who Disher arrested previously and she was worried he would recognize her once he saw her, which he does in the climax.
- Serial Killer: Teresa is a Black Widow-type, having claimed three previous husbands (the third of which was an old case for Randy) and Jonathan was the fourth.
- Skewed Priorities: During the investigation, Natalie's mother takes Randy's bloodied pants (which are evidence, as Natalie points out) because she doesn't like the shade of the tablecloths and wants to show the person in charge the shade she wants (crimson, like the blood).
- Something We Forgot: When Randy tells Stottlemeyer that he doesn't need the wheelchair to get to the reception and ID Teresa, Stottlemeyer races out of there...and has to double back upon realizing he forgot Randy.
- 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.
- Spotting 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.
- Stripper/Cop Confusion: Monk mistakes the cop costume of a male stripper for a real uniform.
- Suspicious Spending: Well, "Suspicious Planned Spending". Lt. Bristo notes to Stottlemeyer that in his talking to Frank Ruttle's sister, he discovered he was looking into buying a house despite being broke and living paycheck to paycheck.
- Tap on the Head: Frank Ruttle is knocked out by his blackmail victim with a rock. It's not what kills him. That would be the mud bath the killer pushes him into.
- 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.
- Worst Wedding Ever: Natalie's brother Jonathan invites her to his wedding, but the photographer turns up dead in a mud bath, Randy (who had come along as a "buffer" between her and her estranged parents) ends up severely injured after being hit by a car, and the bride ultimately gets revealed as a Black Widow, almost ending with her escaping using her new husband as a hostage.
