A woman cheats on her husband with the milkman, or some other man who visits her home on a regular basis while hubby is at work. The image of the slutty milkman was very popular in older works, and persists even though in many places milk has not been delivered to people's homes in decades.
Although there were some Truth in Television incidents of this, it is less based on them than it is the general fear of a person's spouse cheating on them while they're away at work, especially if it's with someone who comes straight to the door. As few milkmen are still working, it is more common nowadays for the wife to cheat with the mailman, plumber or pool-cleaner.
A variant is for this to be the reveal of a Who's Your Daddy? plot. If this relationship produces a child who clearly does not resemble the wife's legal husband it's a case of Chocolate Baby.
See also Cuckold and Pizza Boy Special Delivery for when it's just a random one-off fling with a delivery guy rather than an ongoing affair.
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"If wifie shuns / your fond embrace / don't shoot the iceman / feel your face / Burma Shave"
Invoked in "Liquid Plumr" commercials: two plumbers show up at the house (one with a pipe-snake, and another with a liquid unclogger), speaking in seductive voices... and they literally unclog the woman's pipes.
Comedian Gary Gulman has a routine where he complains about how every time someone finds out that he's the only tall guy in his family, they say, "How tall is the milkman?" — to which he points out that milkmen don't even exist in most places any more, and lists other defunct professionals his mother might have had an affair with, such as the the chimney sweep and the town crier.
"...And the muffin man. Do you know the muffin man?"
Films — Live-Action
In Big Fish, Edward describes how he had dreams which predicted the deaths of his family members just before they happened. Eventually, a dream told him his father would die. After being told this, his father became increasingly paranoid over the next few days. Then the milkman died. (It's a recycling of a pretty old joke.)
Pool boy? Well, Legally Blonde has a subversion of that — the guy turns out to be gay, and his employer genuinely wasn't interested in him, she just wanted some eye-candy while working on her tan (hence his skimpy "uniform").
In Mulholland Drive, Adam Kesher comes home to find his wife in bed with the pool boy (Bill Ray Cyrus!). To add injury to insult, the poolboy is angry that Adam interrupted their sex, and beats him up and throws him out of his own house.
In Chicago, one of the Merry Murderesses tells the story of her husband accusing her of cheating with the milkman, then she says, "He ran into my knife ten times."
In the sci-fi comedy Real Men, when the CIA agent (James Belushi) first meets the meek insurance salesman (John Ritter) he's supposed to recruit, he looks in his fridge and immediately deduces that the salesman's wife is sleeping with the milkman. At the end of the film, the much braver salesman punches out the milkman, as he's entering the door.
Replace "milkman" with "window cleaner" and you have the main plot of the first Confessions film.
Replace "milkman" with "plumber's mate" and you have the main plot of the first Adventures of... film.
Dr. Feinstone in The Dentist finds out that his wife is cheating on him with the poolman. Results are not pretty.
On The Album of the Soundtrack of the Trailer of the Film of Monty Python and the Holy Grail, a logician complains about various logical errors in the film, following multiple tangents to a rant about his wife's affair with the milkman.
A man and his wife are in the hospital, the wife is due to give birth. The doctor offers a new technology which transfers pain to the baby's father instead of the mother. The husband is willing to do anything to help, so he is set up with the device. They set it to 50%, and the wife feels only half the pain — the husband said he felt nothing. They set it to 75%, and the wife feels only a quarter of the pain — the husband again feels nothing. finally they set it for 100% — the wife has a completely pain-free delivery of a healthy child, and the husband never felt a thing. The wife is in such good condition from this that she needs no recovery and they are sent home that same day with their newborn... only to find the mailman dead on the front porch.
Old joke: The man who owns the town drug store notices that the milkman is buying condoms from him every day. Confused, he orders his stockboy to follow him to see what he's up to. The stockboy comes back howling with laughter.
Owner: What's so funny? Where'd he go? Stockboy: Your house.
A young boy stumbled across the perfect phrase to extort adults — "I know your secret." By saying those words, he'd gotten a puppy from his father, a new bike from his mother, and a few candybars from the convenience store owner. On a whim, he said it to the milkman, who embraced the child while exclaiming "Son!"
A man hears his daughter says her prayers "Bless Mommy, bless Daddy and goodbye Grandma." The next day, Grandma dies. Another day she includes "Goodbye Grandpa" and sure enough, he dies too. Then one day she says "Goodbye Daddy," and the next day the man goes to work terrified, being super-cautious all day. He gets home fine and his wife says "You wouldn't believe the day I had — the milkman dropped dead right on our doorstep!" (Alternatively, the body could still be there when the man arrives.)
Referenced in Number the Stars: Jewish Ellen pretends to be part of the Johansen family when the Nazis come searching for her. One of the Nazis notes her dark hair in the otherwise blonde family and sarcastically asks if they got her from the milkman.
In Stephen King's short story, Big Wheels: A Tale of the Laundry Game (collected in the anthology Skeleton Crew) the wife of Rocky, the protagonist left him for the milkman. Even to Rocky, who is a laundry worker, and never reads anything aside from bubble gum comics, this situation has "sonorous classical overtones".
In the Better Than Life sequence in Red Dwarf: Infinity Welcomes Careful Drivers; Rimmer's so screwed up that his "perfect woman" is someone who hates him and has a relationship with the pool boy.
Poet Wendy Cope wrote a villanelle called "Reading Scheme", in which kids from the Dick and Jane books observe that "The milkman likes Mummy. She likes them all." Then comes Daddy and his shotgun...
The anvilicious and conservative Mexican novel Juventud en Extásisplays this trope for drama in the part in which the protagonist's mother tells him about their past: When he was newborn baby and his father was away on a trip she started an affair with an electric appliance repairman. Later she divorced the protagonist's father and married the repairman, who turned out to be an alcoholic, wife-beating child abuser.
Played with as early as the first season of Happy Days:
Joanie: Do you have a best friend, Daddy? Mr. Cunningham: Sure, your mother. Joanie: Who's your best friend, Mom? Mrs. Cunningham: The milkman.
Used in Blackadder. He's talking about Pitt the Younger's little brother:
Blackadder: Who is that? Pitt the toddler? Pitt the embryo? Pitt the glint in the milkman's eye?
Parodied in Home Improvement, where Tim Taylor tells Al that Jill was cheating on him with their supposed milkman as an extremely lame cover story.
Matt Parkman of Heroes suspects his wife is cheating on him with their blond, hunky water delivery man (not without reason, she's cheated on him before). So Matt uses his mental powers to "convince" the man to take a different route.
In the Father Ted episode "Speed 3" Pat Mustard's stint as the Craggy Island milkman results in a lot of suspiciously hairy babies.
Narrator: Dad will be home soon. Better tell Mother she's needed in the kitchen... Servo: ...where the postman eagerly awaits.
Referenced in an episode of Good Eats, of all things. Alton is talking about pasteurization of milk, referring to "the time when we got milk from guys in white suits who went door-to-door"; he opens the door and the milkman turns around... with a handful of flowers. As soon as he sees who he's dealing with, he says "Mister Brown...", hands AB the milk, and beats a hasty retreat.
There's an episode of Tales from the Darkside called "The Milkman Cometh", in it a man hears that their neighborhood's milkman is a deformed freak that no one's ever seen, but apparently will grant any wish that you write down and leave with your empty bottles. This trope comes into play when the guy wishes that his wife will finally have a son. The milkman obliges in the most direct manner possible. Cue Squick.
Used more than once on Maury by men who claim they're not the baby's father. It's almost always disproven.
In one episode of Brazilian sitcom Sai De Baixo, Magda Antibes was recalling childhood memories and the way she was describing a man made her mother realize she was talking about the milkman. When told about this, Magda mentioned remembering the milkman visiting whenever her father was absent.
El Chavo del ocho: Doña Florinda tried to pass a store-bought cake as one she baked by herself. When La Chillindrina decided to tell Professor Jirafales about it, she just told him Doña Florinda was tricking him and that she could ask the baker for confirmation. Professor Jirafales interpreted it another way.
Parodied in a Monty Python's Flying Circus sketch, in which a woman entices the milkman upstairs... and then locks him up in a room containing several other milkmen, two of whom have long white beards and one of whom is a skeleton.
One episode of Midsomer Murders has the delivery boy for a produce store offer... additional services. John Barnaby's wife, on learning about it, expresses disappointment that she only got vegetables.
Heavily implied in Victorious with Mrs. Vega cheating on her husband with his partner. It's more for laughs than anything.
In Red Dwarf, Arnold Rimmer turned out to be the son of the family's dim-witted gardener.
Implied in the song "I'm your Mailman", where every verse is a double entendre.
I don't mess with keys or locks / I just shove it in your box
Referenced in "My Daddy Was a Milkman" by The Kentucky Headhunters.
Some application of this trope led to the name of the punk rock band The Dead Milkmen.
In The Iceman Cometh this joke is repeatedly referenced, but with an iceman instead of a milkman. A few examples:
Rocky: Yeah, some kidder! Remember how he woiks up dat gag about his wife, when he's cockeyed, cryin' over her picture and den springin' it on yuh all of a sudden dat he left her in de hay wid de iceman? [...] Chuck: And I tells her I'm off de stuff for life. Den she beefs we won't be married a month before I'll trow it in her face she was a tart. "Jees, Baby," I tells her. "Why should I? What de hell yuh tink I tink I'm marryin', a voigin? Why should I kick as long as yuh lay off it and don't do no cheatin' wid de iceman or nobody?" [...] Cora: Aw, yuh shouldn't make dat iceman crack, Rocky. It's aw right for him to kid about it but—I notice Hickey ain't pulled dat old iceman gag dis time. (excitedly) D'yuh suppose dat he did catch his wife cheatin'? I don't mean wid no iceman, but wid some guy.
[My husband] says, "You been screwin' the milkman?" He kept on screamin', "You've been screwin' the milkman!" And then he ran into my knife. He ran into my knife ten times.
In Street Scene, Mrs. Maurrant's affair with Sankey, the collector for the milk company, is a frequent subject of their neighbors' gossip. One hot day, Mr. Maurrant comes home unexpectedly early, catches them together and shoots them both.
Implied in the Classic Disney ShortFather's Day Off. Goofy is taking his wife's place for the day, so when the milkman comes, he absent-mindedly gives Goof a kiss on the lips. The same thing happens with the grocery guy, and the laundry guy.
The episode "Insecurity" on South Park modernizes this trope with the UPS delivery driver while frequently alluding to the old milkman story.
Heavily implied in the Futurama episode "A Clockwork Origin." Professor Farnsworth cleanses the water on a barren planet, and says it's "as sterile as my milkman-trusting father."
Implied as a gay relationship in The Simpsons, with this one-off like from Moe: "Ah, my physical pain is gone! Now I can focus on my criplling emotional pain. Oh daddy why, why wouldn't you ever hug me! You hugged the mailman!"
The original Love Interest to the main character of City Hunters dumps him because she's been dating her personal trainer and liked him more.
It's not rare for tactless people to suggest that children who don't resemble either of their parents are results of "visits with the milkman".
In Spain, the equivalent of the milkman joke is about el butanero, the man that delivers liquified gas in a metal cylinder◊. Those cylinders are quite heavy, and since the guy is expected to carry and deliver them in person (even if the house is on the top floor of a building with no elevator) it's understandable why he's de facto considered to be taller, stronger and manlier than any other professional. It's also quickly becoming a Dead Horse Trope now, as electric heating and stoves are replacing natural gas (plus many places retaining gas heat and stoves are getting gas lines, obviating the need for cylinders).
According to the "canon" of The Church of the SubGenius, J.R. "Bob" Dobbs' father was either Xinucha-Chi-Xan M. Dobbs or an itinerant mailman.