Raymond: —Says the man who married a stripper, then divorced a stripper, then married a regular person, then hung in there for three whole months.
Some people just can't seem to make it work. They go through divorce after divorce and never seem to learn their lesson. These characters are typically middle-aged, otherwise successful men, but none of these are requirements. The only requirement is that the character has been through at least two divorces.
There are numerous reasons for a character's marriages to repeatedly fail. Sometimes a needy best friend drives a wedge. Sometimes the character is still too devoted to a lost loved one. Maybe they're even trying to replace a lost love, and the divorces result because the new spouse is simply not the old one. Perhaps they are marrying with the expectation of getting divorced and receiving alimony. Maybe they have issues concerning commitment and fidelity. Maybe they are attracted to Broken Birds and the Troubled, but Cute, and erroneously think they can "fix" that person...only to find that a) they can't and b) the other person resents being expected to change, or being treated like a project instead of a person. Usually, it's because they're simply Married to the Job.
This trope is often part of a character's Dark and Troubled Past, but it can also be Played for Laughs. In both comedies and dramas, the character is often part of a Dysfunction Junction. As it is exceedingly common on crime dramas, this is one element of the Standard Cop Backstory.
Bear in mind that an end of a marriage doesn't necessarily constitute a divorce. If the character has been married twice, but one of the marriages ended in death, it doesn't count.
- In the Daria fic "God Save The Esteem," Amy mocks Rita about her failed marriages, only for Rita to bitterly remind her that "You're still winning that race." It turns out that Amy's been married four times (though she doesn't like to count the one in Vegas).
- In the Pokémon fic "Siebold's Special Guest", the eccentric socialite is married to her thirteenth husband.
- In the film version of Jurassic Park, Ian Malcolm comments at one point that he's always looking for the next ex-Mrs. Malcolm. It's implied that all of his marriages ended in divorce.
- The movie The Marrying Man centered on a couple who married each other and then divorced multiple times over the span of decades. By the end of the movie they are about to get married for the fourth time.
- In The Heartbreak Kid (2007), Ben Stiller character Eddie rushes into marriage with Lila. During the honeymoon, he realizes how mismatched they are and meets another woman Miranda. After many mishaps, both women leave him. Years later, he is settled in Mexico, and Miranda visits him. In the final scene he makes plans to go on a date with her and after she leaves, it is revealed that he is married to a third woman, and possibly is going to divorce her to be with the One.
- Ma Flodder from the Flodder movies has been married 5 times, but is currently single again.
- Osgood Fielding from Some Like It Hot has been married seven or eight times (his mother is keeping score) and plans to marry again, even after he finds out that his fiancée is a man in drag.
- Hortense Ditherwell (Alice Brady) in The Gay Divorcee has been married three times and is looking for a fourth.
Hortense: Let's see, I didn't marry in 1929 or '30. That was the year of the crash, and men didn't know whether they had money or not.
- The princess in The Palm Beach Story has possibly been married six times; she's had three divorces and two annulments, and she says she's "not quite through with the Prince" (although she is certainly looking for candidates to replace him).
- Mrs. White from Clue is a combination of this trope, Black Widow, and Really Gets Around.
Col. Mustard: How many husbands have you had?Mrs. White: Mine or other women's?Col. Mustard: Yours.Mrs. White: Five.Col. Mustard: Five?Mrs. White: Yes, just the five. Husbands should be like Kleenex: soft, strong and disposable.
- Maria Ragetti from Grumpier Old Men has five ex-husbands. Her mother convices her that she is "cursed in love" and talks her out of pursuing a relationship with Max. The two end up marrying by the end of the film.
- In The Mark of the Lion trilogy, Julia Valerian goes through three husbands, one fiancé, and multiple lovers. Two of the husbands die, but relations with the fiancé and one of the husbands are broken off by divorce.
- In The Devil Wears Prada, Miranda is preparing to marry her ninth husband.
- 1066 and All That's genealogical table of English kings shows John of Gaunt as having been married to Lady Godiva, Margaret of Angoulème, Joan of Arc, The Infanta, The Maria Theresa, Ann of Geierstein, etc. and etc. etc. The text also states that Henry VIII had VIII wives, and that he considered marrying a Good Thing. There was also the Scottish queen Mary, who had so many husbands that she was known as Mary Queen of Hearts.
- Helene Roffe-Martel in Sidney Sheldon's Bloodline has several ex-husbands. All of whom she married to become wealthier than she already was. Her current (at the book's time) husband is a henpecked one she married because he was a nothing she could mould into whatever she wanted.
- In The Goblin Emperor, Maia's father, the previous emperor, divorced his first wife for barrenness, then went through a number of wives who all died before their thirtiest birthday, apparently for natural causes. His banishing the Empress Chenelo, Maia's mother, to a remote country estate can be considered the equivalent of divorce, as he never saw her again. Upon his death at the start of the novel, he leaves a widow who is about as old as his youngest son, Maia.
- Game of Thrones: Sansa is put in an Arranged Marriage four times. With Joffrey in Season 1 (although the wedding itself never happens), then with Tyrion in Season 3, then with Robin (doesn't pass the engagement part) then with Ramsay in Season 5.
- Margaery as well, with the benefit that she manages to marry a king each time: First Renly Baratheon (to whom she is The Beard; he prefers her brother and hence never consummated their union), then Joffrey Baratheon (who dies on their wedding feast before consummating the marriage), and finally Joffrey's younger brother Tommen Baratheon.
- Wilson on House had been divorced twice at the start of the show. He went through his third divorce in season two.
- Gibbs on NCIS has three ex-wives, though he has actually been married four times.
- On Criminal Minds, Rossi has been divorced three times.
- On Castle, the titular character has two ex-wives.
- On Law & Order, Jack McCoy has been divorced twice. Lennie Briscoe also has multiple ex-wives, although the exact number is unknown.
- Briscoe's associate John Munch from Law & Order: Special Victims Unit has been divorced no less than four times.
- Guinan on Star Trek: The Next Generation has been married 23 times. It's not clear if all these marriages ended in divorce, or if she outlived some or most of her husbands.
- This trope is standard practice for Trill symbiotes, as their marriages are considered to end automatically if they transfer to a new body. Dax on Deep Space Nine had been married so many times in various former host-bodies that when Worf insisted on a traditional Klingon wedding, she agreed to everything he wanted, simply because she was so completely bored with doing the Trill traditions every time (and because it meant so much to him).
- Ross on Friends had three ex-wives by the end of the series, and was often mocked for it (sometimes by himself).
Ross: I'm gonna go out on a limb here, but No Divorces in '99!Monica: Aren't you still married to Emily?Ross: Just The One Divorce in '99!
- John Munch from Homicide: Life on the Street and Law & Order: Special Victims Unit had two ex-wives in his past, married a bartender in Homicide's last season, and had divorced her by the finale movie. There was a reason he always got teamed with Briscoe during crossovers.
- By SVU, he's been married (and divorced) four times, and states that he still believes in true love, but that it always eludes him.
- Ron Swanson on Parks and Recreation has two ex-wives named Tammy, which is also his mother's name.
- On Community, Pierce has been divorced seven times.
- Al Calavicci of Quantum Leap had five wives, three of which are confirmed to have left him in a divorce (or divorce-like circumstances), and one is implied to. Only the first one really "worked": She only left him because she waited long enough after he was declared dead. The series finale gave Sam a chance to change all that by telling her Al was still alive and would come back to her. The epilogue explains that as a result they stayed together and had Babies Ever After instead
- On My Name Is Earl, Earl has been married three times. The first time was an Accidental Marriage to Joy, until she left him (while he was hospitalized, no less!) for Darnell. The second time was to a friend's elderly mother, until she wanted sex and he didn't want to give it to her. The third time was to a friend's ex-girlfriend who wanted to follow in his footsteps...then morphed into a Yandere when he was more focused on the list than on her, before she finally left him to join an Amish-like settlement, doing him a final favor by leaving him all the money she got in her court settlement. Earl states that despite all their problems, Joy was his favorite wife.
- In the same series, one guy on the list is a man who's been married a few times in his life, and Earl slept with at least two of his wives, on multiple occasions.
- Doctor Who,
- It is mentioned that Cassandra was married nine times.
- The main character also fits. Besides the hypothetical grandmother of Susan, he married Cameca the aztec woman, River Song, Elizabeth I and Marilyn Monroe over the course of the series.
- River Song marries the Doctor in "The Wedding of River Song" but in "The Husbands of River Song", we learn she also married Hydroflax, Ramone and Stephen Fry. She also had at least two wives (one of whom is Cleopatra).
- Multi-millionaire Corrupt Corporate Executive Wilfred Tipton of the Suite Life franchise has been married and divorced anywhere between eight and fifteen times (London can never seem to remember just how many).
- On Scrubs, JD mentions that after his parents got divorced, his mother "started marrying everyone who rang the doorbell."
- Mickey from Seinfeld, and he seems to take pride in it. When meeting a woman who is distraught over the possibility of her second marriage ending, he laughs and calls her a "lightweight" before walking out with his newest wife-to-be.
- On The Munsters Grandpa has been married 166 times. However, it's not known if all the marriages ended in divorce or not.
- On Charmed, Grams was married six times; she was quite happy with the girls' grandfather, who was killed by a demon, but the next five husbands left her with a decidedly poor outlook on men.
- Lt. Provenza of The Closer and Major Crimes was married four times (twice to the same woman). He nearly got married for the fifth time but they broke up.
- John Sheridan of Babylon5 is far from the worst example of this trope, but he has been married enough times to cause Garibaldi to exclaim, "How many wives does he have?" Just three.
- NTSF:SD:SUV::: Agent Trent Hauser mentions that he's been married six times. His bos Kove has been married eleven times, including with Trent.
- The narrator of the George Strait song "All My Ex's Live in Texas."
- In The Four Gospels, the unnamed Samaritan woman who chats with Jesus at the well has been married and divorced five times, making her a social pariah. (Which is why she went to the well by herself in the middle of the day, rather than at dawn or at dusk like most women would.) She was apparently living with a boyfriend (who likely already had a wife, making her The Mistress).
- The Simpsons:
My name's already Selma Bouvier-Terwilliger-Hutz-McClure. God knows it's long enough without Nahassapeema-whatever.
- One of Marge's sisters: Selma Bouvier-Terwilliger-Hutz-McClure-Anderson-Simpson-D'Amico. She refused to have a Citizenship Marriage with Apu Nahasapeemapetilon just because his name is too long.
- In fact, the only marriage she had that didn't (technically) end in divorce was to Disco Stu, who got an annulment from the Catholic church.
- Lurleen Lumpkin (a country singer that tried to seduce Homer) has been married 5 or 6 times, all to men that look and act just like Homer.
- The creator of Malibu Stacy (an Expy of Barbie) has been married to 5 different men, mainly parodies of Ken and G.I. Joe. She's single now, and lives her life in a pink mansion (made to look like Bar-uh...Malibu Stacy's Dream House) as a Lady Drunk. Lisa talks her into creating a new doll, after finding that a talking Malibu Stacy doll was spewing sexist drivel.
- In Family Guy, Lois' sister, Carol has been divorced nine times. She's currently married to Mayor Adam West.
- On Hey Arnold!, Arnold has been left some money by a lounge singer that he had helped to rediscover his talents in an earlier episode. At the will-reading, are several different blond women that he had been married to at one point or another.
- On Daria, Jane's oldest brother Wind is on his third or fourth wife by the time he first shows up. In this case it seems to be because he's a neurotic mess who jumps into relationships with less-than-stellar women (he insists Wife #3 "isn't like the other ones").
Relative: And [how's] your brother Wind?Jane: He's thinking about getting remarried if he can just figure out whether his divorces were legal.
- Elizabeth Taylor was married eight times including twice to Richard Burton. Her third marriage ended when her husband died but all the other ones ended in divorce.
- Burton himself was married five times, including his two marriages to Taylor. Only his last one didn't end in divorce.
- Pamela Anderson has been married four times (twice to the same person). None of these have lasted more than 3 years, to the delight of late-night comedians.
Michael K.: You know how some hos say that break-up sex is the best kind of sex? Maybe Pamela Anderson is way past that and she can only bust a nut if she’s freshly divorced from the dude.
- Larry King was married eight times, to seven different women. All but the last marriage (his longest one yet) have ended in divorce.
- Zsa Zsa Gabor had nine husbands during her lifetime. The first eight marriages ended in divorce, except one that was annulled. Her ninth husband outlived her.
- Her older sister Magda was married six times, and her younger sister Eva was married five times. Their mother was married thrice. Guess it's in the blood?
- Mickey Rooney has been married eight times and divorced seven times. He was married to his eighth wife for over 35 years from 1978 until his death in 2014, which was more than the length of all of his previous marriages combined; however, they were separated for the last few years.
- Henry VIII of England is probably the...er, king of this trope. He created an entire church (with him as the boss) in order to get his marriage annulled. He married six times in total; two of his marriages were annulled, three ended in the wife's death (twice with a bit of help from Henry), and the last ended with Henry's death.
- Baptist minister Glynn Wolfe, married 29 times, altough not all his marriages ended in divorce. His last marriage, solely a publicity stunt, was to Linda Lou Essex, who was married 22 times before.
- Norman Mailer was married six times (though his marriage to Carol Stevens, which lasted for one day, was only to legitimise the child they had together). He famously ended up stabbing his second wife, Adele Morales, albeit non-fatally; he was shipped off to Bellevue to cool out. "I really was in danger of being declared insane because I'm a Jew, and the doctors were all Jewish, and Jews just don't do this sort of thing unless they are really crazy." But he was let out.
- Musician Ben Folds has been married and divorced 4 times, and currently has a girlfriend.
- German chancellor Gerhard Schröder was elected in 1998 just one year after entering his fourth marriage with a much younger woman, earning nicknames as the "Lord of the Rings" and "Audi-Kanzler" (German car manufacturer Audi has four rings as their logo).
- His vice chancellor and secretary of state Joschka Fischer had been married three times by then, drew even the next year, marrying an even younger woman. It didn't quite work and he finally surpassed Schröder in 2005 by saying the vows for the fifth time (needless to say, she's only slightly older than her predecessor).
- Richard Pryor was married seven times to five different women. His last and longest marriage, which ended with his death, lasted for four years. All the other ones ended with divorce.
- Billy Bob Thornton has been married six times and divorced five times; his longest marriage lasted for four years. After five unsuccessful marriages, he lived with Connie Angland for 11 years before marrying her in 2014.