December–December Romance

They're a bit late on "grow old together," but they'll make do.

Amy: They're really perfect for each other.
Glenn: They are. They're both old.
Amy: Yeah, and there's, like, this whole duck thing, but mostly they're old.

— Superstore, "Valentine's Day"

Romantic love that arises between two elderly or senior characters. May be depicted tragically in works where mortality or mental illness is a theme, but it can also be used optimistically, as proof that love and dating have no age limits.

Compare May–December Romance and Grow Old with Me. It often overlaps with New Old Flame, if the two characters were lovers earlier in life but got separated for some reason. It is the opposite of Puppy Love, in which two unusually young characters have a romance — although in the New Old Flame case, the same pair of characters may have been both. It can also serve as a case of Second Love.

It's definitely a case of Truth in Television, as many people do remarry or have long-term relationships that begin very late in life.

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Examples:

Advertising

• This McDonald's commercial features the beginnings of one.

Anime & Manga

• In Full Moon, this becomes the case for Fuzuki and Seijurou. The two met in their teen years and loved each other, but because Fuzuki's best friend was also in love with Seijurou, mistakenly thought the two had betrayed her and said friend (Moe Rikyou, aka Meroko) committed suicide, Fuzuki was too heart-broken and guilt-ridden to pursue a relationship with Seijurou after all. It's not until decades later that Seijurou sees Fuzuki again and the two are seen holding hands in the final chapter.
• Discussed in Kaguya-sama: Love Is War when the student council is playing a Game of Life/Sugoroku mashup and Kaguya (who's been projecting her fantasies and worries onto the game) lands on a marriage space near the end of the game. However, due to her having gotten a "Can't trust men" card back at the beginning, she doesn't end up with Shirogane. She ends up with Fujiwara.
  Kaguya: Did it take him until old age to notice my charms...? But a quiet twilight of my life where I can finally find true love, I suppose that doesn't sound too bad.
• Naruto: Tragically subverted with Jiraiya and Tsunade. Jiraiya spent most of his life as the Unlucky Childhood Friend but after a lot of interpersonal drama and Tsunade managing to reconcile with him and her old idealism thanks to Naruto, it looks like she might have been willing to give him a chance now that both of them were in their fifties. Unfortunately, Jiraiya heads off to the Hidden Rain Village to gather intel on the leader of the Akatsuki and ends up fighting and dying to Pain, right after he made a bet with Tsunade to bet against him since she almost always loses to assure her. Jiraiya dies noting his inability to win Tsunade's heart as just one of his many failures, and Tsunade is left heart-broken at realizing one of the only dear friends she had left is now dead.
• In Ōoku: The Inner Chambers, Tsunayoshi and Emonnosuke knew each other for years, and it's implied from the start that they were smitten with each other, but what with Emonnosuke being too old to be a concubine, and later Tsunayoshi's need to conceive a new heir after the death of her daughter, they were unable to confess their love to each other until their older years, certainly after Tsunayoshi hit menopause. The day after they have sex for the first time, Emonnosuke dies from an aneurysm.
• An episode of Sailor Moon Super S features a snippy but secretly kind old woman named Mayako, who strikes an Intergenerational Friendship with Chibiusa and Mamoru. It turns out that the reason why she's so bitter is that she lost her old boyfriend twenty years ago, which made her a borderline Broken Bird. Said boyfriend, a famous Supreme Chef Ichiro Ohno (whom Makoto is a huge fan of), returns into her life towards the end of the episode (after Mayako is saved from Hawk Eye by the Senshi) and apologies to her for the hurt he caused her, and they get together again and open a restaurant — like they had sworn to do many years ago.

Comic Books

• DC Comics:
  • Green Lantern Alan Scott and Molly Mayne, AKA Harlequin, one of his rogues from back in the day. They got back in touch and eventually married in Infinity, Inc.. There was some friction in the marriage, though, as the lantern kept Scott physically young while Mayne aged naturally. In despair, she made a Deal with the Devil in the crossover Underworld Unleashed, prompting a horrified Scott to enter Hell to rescue his wife's soul. Later, however, Scott was aged to his actual chronological age.
  • Kingdom Come is set in an alternate future and briefly shows that Catwoman and the Riddler got together at some point, which is the only reason Lex allows the latter to join the Mankind Liberation Front.
• Chief and the title character's mother in Doug TenNapel's Earthboy Jacobus, which actually gets more focus than the title character's romance.
• The Simpsons Futurama Crossover Crisis: Mr. Burns and Mom (who are among the oldest people in their respective series) fall in love with each other after the former ends up in New New York alongside other Springfieldians.
• Spider-Man:
  • Aunt May and J. Jonah Jameson Sr.
  • Also, Aunt May and Edwin Jarvis. However, it didn't end well because it turns out that "Jarvis" is actually a Skrull impostor, and has been for a while. The real Jarvis has likely never met her.

Comic Strips

• Gran and Peter Kiesl in 9 Chickweed Lane — though this was a rekindling of a romance they had a half-century earlier.
• For Better or for Worse:
  • Grandpa Jim meets his Second Love Iris two years after his wife Marian's death. They move into a seniors' housing complex together, elope three years later, and remain Happily Married, despite Jim's escalating health problems, until his death.
  • The Pattersons' neighbor, elderly widow Thelma Baird, moves into a seniors' residence and starts dating a widower named Ed Smith who also lives there.
• Jump Start: Maureen (Marcy's mother) gets married to Clayton (father of Marcy and Joe's next-door neighbor, Clarence).
• The titular character of Mary Worth is in one of these with another resident of her condo complex. It's not the only example of this trope in the strip: a more recent storyline had an elderly neighbour who was facing moving into a retirement home fall in love and marry a man living at the home, as well.

Fan Works

• In Leave Your Spirit, Katara and Zuko slept together once and had Kya from that. Katara never told either her husband Aang, Zuko, or even Kya herself about her daughter's parentage. Decades afterwards, long after Aang's death, Zuko and Katara meet again. The fic ends on a Maybe Ever After ending.
• Zuko and Katara getting together during the time of The Legend of Korra fics (when they’re in their late eighties/early nineties) are very popular. Katara has been widowed for seventeen years by the time of the show but what makes this Fanfic Fuel is that Zuko’s marital status has never been confirmed one way or the other. He has a daughter and two grandkids, implying he’s been married at one point, but it’s unclear to whom he is/was married or if he’s widowed as well.
• In Hero: The Guardian Smurf, Papa Smurf falls in love with and marries his Opposite-Sex Clone Mother Smurfette, who physically is also the same age as he is.

Films — Animation

• In The Swan Princess, there's Queen Uberta and Lord Rogers. The original film gives them a Maybe Ever After, although the sequels reveal that it doesn’t last, particularly because Uberta’s long-lost husband eventually turns out to be still alive. There's also some hints at Queen Uberta/King William in the first film, but King William goes and dies.

Films — Live-Action

• The Adventures of Priscilla, Queen of the Desert has country mechanic Bob falling in love with aging trans woman Bernadette after her much younger husband dies and his much younger wife leaves him.
• American Fiction: Monk's mother's housekeeper rekindles a romance with a cop from the town where they have a beach house and she has a Fourth-Date Marriage with him, but it's portrayed as a good thing and not something irrational. They obviously had a prior thing for each other and decide to waste no time since both of them are probably in their sixties, if not older.
• The Best Exotic Marigold Hotel is full of this, notably a rare gay version with Graham and his childhood sweetheart/servant.
• Cat's Play: Between Erzsi and Viktor, both now in their seventies, who live in the same apartment building. Towards the end, Erzsi reveals to her sister that it's a matter of Old Flames reuniting, that she and Viktor were lovers when they were young and continued their relationship even after she got married. Erzsi only broke it off back in the day after her husband had a health scare and came out of a life-or-death surgery.
• Children of Nature is about two old folks who meet in a Bleak Abyss Retirement Home, fall in love, steal a car, and escape together.
• Guillaume Blerot and the Widow Audel in Chocolat.
• Grumpier Old Men has Grandpa Gustafson having a romance (in his own way) with Mama Ragetti, the mother of Maria Ragetti. When God finally remembers him, Mama is among the mourners at the funeral and tosses a flower into the grave with him.
• The Intern: Ben (whose wife recently passed away) hooks up with Fiona, a masseuse at the same company he now works at who's almost his own senior age. They even go to the funeral of one of Ben's friends for a date.
• Louisa: Louisa, a widow in her seventies, falls for Henry, the neighborhood grocer, a widower also in his seventies. It becomes a December-December Love Triangle when Abel (boss to Louisa's son Hal) falls in love with Louisa as well.
• A Prairie Home Companion: Country singer Chuck Akers and the crew member he is engaged in a whimsical romance with are both about seventy.
• Claire and Lorenzo in Letters to Juliet, who were separated when they were teenagers, married other people and after fifty years, were reunited and married. Made even better by the fact that they are played by Vanessa Redgrave and Franco Nero, who similarly married later in life after an early romance and separation.
• A Piano For Mrs Cimino has Esther Cimino, an aging and widowed retired piano teacher, meeting and soon dating her long-lost friend Barney Fellman.
• In The Princess Diaries 2 (the Disney film, not the books), Joe the head of security falls in love with the dowager queen. Their dialogue suggests that they've had a sort of love affair for quite a while, but are only now admitting it... and they finally decide to get married in the end.
• Ivan Simanov and Victoria in Red (2010). They're well into their sixties and clearly enamoured of each other, which qualifies them. Played with because they were originally lovers as young adults before their jobs — and the fact that they were on opposite sides of the Cold War! — separated them. December/December rekindling, perhaps?
• In Robot and Frank there is clearly a spark between retired jewel thief Frank and Jennifer the librarian, played by Frank Langella and Susan Sarandon. She is his ex-wife, but his memory loss is so bad that he no longer remembers her.
• Shadowlands: Both Jack and Joy were in or near middle-aged at the time of their marriage.
• In Six Degrees Of Celebration 2, two of the characters, now well into their sixties, haven't been in contact for forty years because the man's letter of reconciliation was never delivered. The letter is found during repair work at the post office and the woman rushes off to meet her sweetheart, but by now he had given up hope and left on a long-distance flight. The film's main plotline centers around their relatives as well as chance acquaintances trying to bring the couple together at last.
• Something's Gotta Give has Jack Nicholson's character opposite Keanu Reeves's, competing for the affections of the beautiful older woman played by Diane Keaton. Even worse/better, she's the mother of his last girlfriend.
• Steam (2007): Doris is at least in her seventies, dating a man around her age.

Literature

• 1632:
  • Schoolteacher Melissa Mailey and Dr. James Nichols. Both are in their late fifties at the time of the Ring of Fire, and they're both pleasantly surprised to find that they haven't... lost the capacity for enjoying each other. Which they do. On a regular basis. It's a mark of Melissa's Character Development that she throws propriety to the winds and starts openly living in sin with him.
  • Mayor Henry Dreeson and Veronica Richter, grandmother of Gretchen and Hans.
• Captain Underpants: George's great-grandmother and Harold's grandfather hook up around the end of The Preposterous Plight of the Purple Potty People. George and Harold were suitably squicked in-universe from being present to them passionately kissing before going off to find a restaurant for a date.
• Diary of a Wimpy Kid: Grandpa Heffley is still into dating, as shown in Hard Luck and Old School. Greg's surprised to see this.
• In Judy Blume's Fudge-a-Mania, Peter Hatcher's widowed grandmother gets married to the widower grandfather of Peter's Sitcom Arch-Nemesis Sheila Tubman.
• Quite a common theme in Iris Murdoch's works (well, sometimes in October-October way).
• In the Jeeves and Wooster story "Indian Summer of an Uncle", Bertie's Uncle George has an "Indian summer" and goes after a girl much younger than himself. Then he meets the girl's aunt, who turns out to be the lost love of his younger days, and marries her instead.
• The Little Coffee Shop of Kabul: Halajan and Rashif are two elderly people who have been in love for years despite not being arranged to marry. They've been secretly conversing via letters for years, and finally marry at the end.
• Malê Rising has Usman Abacar (a West African soldier and politician) and Sarah Child (a British high-society woman) marrying once their respective spouses have died.
• Max & the Midknights: The Tower of Time: In this installment, Mumblin' the Magician has started seeing a sorceress from around the Kingdom of Klunk named Beatrice. They typically engage in calling each other by cutesy nicknames.
• In Memory, Lady Alys Vorpatril (age 55) and Simon Illyan (age 60, perhaps older) get together after Illyan's medically forced retirement. At some point in the series, it's also mentioned that Miles' Betan grandmother (who is 90 if she's a day) is in a similar relationship with a gentleman in his 80s.
• Safehold: Two of Sharleyan's biggest allies during her reign as Queen of Chisholm and, later, Empress of Charis, were her mother Queen Mother Alahnah and her First Councilor and the Baron of Green Mountain, Mahrak Sahndyrs, who had served Sharleyan's father before her. Midway through the series, Green Mountain is grievously injured following a terrorist attack by the Inquisition's Rakurai agents. His injuries forced him to step down from his role as First Councilor and, in his retirement and rehabilitation, he and Alahnah become a couple, much to Sharleyan's delight.
• Stephen King:
  • Paul and Elaine in The Green Mile.
  • Another instance with Phil and Pauline in the story "Herman Wouk Is Still Alive" (found in The Bazaar of Bad Dreams).
  • And another with Ralph and Lois in Insomnia. Also a Second Love situation, since both had happy marriages until their respective first spouses died.
• In The Stormlight Archive Dalinar Kholin and Navani Kholin. They are both in their fifties, he used to court her but she finally chose his brother Gavilar. The marriage resulted in two children but did not seem to be very happy. After her husband's death and Dalinar's near death, Navani finally decides to throw propriety to the winds and get together with the man she really loves. At first, he objects, because it's against the society's rules. He gets over it, though.
• Tamora Pierce:
  • Eleni Cooper and Sir Myles in the Song of the Lioness quartet. Very sweetly portrayed.
  • In the Circle of Magic books, Sandry ships her great-uncle with a dance instructor his age.
• Terry Pratchett:
  • In Going Postal, the delivery of a letter results in two childhood sweethearts, now elderly and widowed, getting married after all.
  • Also seen with Mr. Weavall in A Hat Full of Sky.
• Yours Truly: Truly Lovejoy notices that Belinda Winchester and Augustus Wylde, the town's local romance novelist, seem to be getting sweet on each other.

Live-Action TV

• Present in the Britcom As Time Goes By.
  • Young lovers, a soldier and a nurse, lose contact when he's shipped off to the Korean War. They're reunited in their golden years. Counts as both a case of this trope and Grow Old with Me.
  • Another example from the same show is Lionel's father Rocky and his lover Madge, who get married in their eighties.
• Admiral Adama and President Roslin in Battlestar Galactica, although they are middle-aged rather than elderly. Also Fire-Forged Friends, since they did not get along well at first. Hell, he even deposed her once. (And re-posed[sic] her another time.)
• The Beauty Queen Of Jerusalem:
  • Mercada attempts to hit on Luna's boss Mr. Zacks, who's of a similar age to her, after she notices he's unmarried, but unfortunately for her he's gay.
  • She has more success with Avram, an old family friend who she starts courting after his wife dies.
• Kelly and Yorkie in the Black Mirror episode "San Junipero" are this. While they appear as their younger selves with their digital avatars in the titular Artificial Afterlife, their real-world selves are elderly women.
• Major Garreau and Sergeant Pepper in China Beach with a bit of an eventual tearjerker implied late in the last season when it's mentioned that Sarge has cancer and may not be long for this world.
• A weird example in the Doctor and the TARDIS on Doctor Who. The first time they met in human form, they were both several hundred years old. On the other hand, they had been "together" for several hundred years before that too, without the Doctor really grasping how explicit the relationship was. On the other hand, when they first met, they were both instantly smitten with each other and ran off together, the TARDIS was already very old (an antique in fact) at that point, and it's implied the Doctor's first incarnation may have been rather old at the time too (although he was young by Time Lord standards). On the other hand, she's a sentient starship/time machine and he has a case of The Nth Doctor going on, so when they first meet in human form, his body appears to be in its late twenties and hers appears to be thirtysomething, so it's debatable whether it qualifies for this trope. On the other other hand, it's debatable whether a couple this bizarre properly qualifies for any romance trope, so...
• Julian Fellowes is particularly fond of this trope in Downton Abbey.
  • The fifty-something Carson, the butler, and the fifty-year-old Mrs Hughes, the housekeeper, were supposed to be Married to the Job and Platonic Life-Partners, but soon became a Fan-Preferred Couple. The Word of God was aware of it and although he used to say that they wouldn't get together, liked teasing the fans, by some Green-Eyed Monster from Carson's side and some Ship Tease from both sides. However, after 5 seasons, 12 years on screen, they get a Relationship Upgrade at the end of the 5th season. Unfortunately, after their wedding, it almost receives the Shipping Bed Death trope from Carson's nasty behaviour towards his new wife and poor plotlines.
  • Dr. Richard Clarkson and Mrs. Isobel Crawley were a Fan-Preferred Couple after his almost-proposal. When Lord Merton, another Silver Fox, takes an interest in Mrs. Crawley, it becomes a Love Triangle. It's hinted in the 5th and 6th seasons that there is some Green-Eyed-Monster on Dr. Clarkson's side. In the end, Mrs. Crawley chooses Lord Merton.
  • The Dowager Countess had an affair with the Russian Prince Kuragin, while they were both married. In the 5th season, he appears as the possibility of New Old Flame.
• In one episode of Everybody Loves Raymond, Debra's father is shown to have remarried and wants to bring his new wife to Thanksgiving. Debra is upset, although Ray points out that if her mom is happy, she should be happy. Everyone is expecting a May–December Romance, only for the woman to actually be older than him (the age is never stated, but Debra's father looked to be in his 60s and his new wife looked to be in her 80s).
• The Golden Girls:
  • Happened when Sophia fell in love with a man she met on the boardwalk. Sadly, it was hinted at during the episode and revealed at the end that he had Alzheimer's, so they had to cut it short because he was going to be put in a home.
  • In another episode she falls in love with her late best friend's husband. They get married but realize it won't work out between them so they decide to separate.
• Happened with a couple of guest characters (both widowed) on Good Times. It was mentioned that as a married couple they could get more from social security than if they were single.
• Elka, a senior citizen, in Hot in Cleveland has multiple romantic interests of her same age just in the first season.
• Last Tango in Halifax is about a couple in their seventies who, due to miscommunication, never got together in their teens, meet again on Facebook and get engaged the day they reunite in person.
• Gaius and Alice on Merlin (even though they had met, nearly married, and broken up prior to the episode, it was still a late-in-life relationship).
• Modern Love: Margot and Ken are both elderly when they start seeing each other.
• On My Name Is Earl, Earl accidentally slept with his friend Ralph's mother while drunk, and to make up for it, he gets forced into a Shotgun Wedding. He likes being married to her, except for one little thing: she wants to consummate their marriage, and now that he's sober this time, is Squicked out by the idea of having sex with an old woman. After he makes excuse after excuse after excuse, he decides he's going to get drunk and "do his husbandly duty." But before he can do so, he finds her in bed with his elderly bandmate. It turns out he's a much better match for her than Earl is, and Earl has the marriage annulled. Meanwhile, Mrs. Mariano keeps seeing Earl's former bandmate.
• Silver Foxes Agent Gibbs and Dr. Ryan on NCIS, though sadly it doesn't last.
• Star Trek: Deep Space Nine has Zek and Ishka, i.e. the romance between the leader of the entire Ferengi Alliance and Quark's mother. Quark didn't take it very well, not least because the Ferengi government had forced him into exile a while back and Zek didn't seem to think this was any sort of barrier to pursuing a relationship with his mother. It didn't seem to deter Ishka very much either, but then Quark always was The Un-Favourite...
• In Season 3 of Shtisel, Shulem's brother-in-law Issachar was about to marry his First Love Nechama, but suddenly dies. Shulem floats the idea of the two of them getting together, but she doesn't like him in that way. She does find a kindred spirit in his brother Nuchem, though, who loves classical music just like her.
• In the Valentine's Day Episode of Superstore, Amy and Glenn scheme to set up two senior employees. Lampshaded as they mainly do it because the two are elderly.
• This Is Us has a flashback episode showing Dr. K (the elderly doctor who delivered two of Rebecca and Jack’s children) still mourning his late wife who died a year earlier and is reluctant to move on. After delivering the Pearson’s children and giving Jack some life advice, he himself is inspired to try to live life again and reaches out to his (also elderly) female neighbor Anne to take up her offer to make him dinner one night which he earlier brushed off. Eighteen years later he and Anne reappear at Jack’s funeral where he introduces Anne as his wife.
• The Twilight Zone (1985): Implied in "Dream Me a Life". After the elderly retirement home resident Roger Simpson Leeds helps Laurel Kincaid overcome her grief at her husband's death in her dream, he asks the spirit of her husband why he called him into the dream. Her husband replies, "I think you know." The next morning in the real world, Roger dons a nice suit and takes Laurel to breakfast.
• Two of a Kind has Mary-Kate and Ashley invoke this in the first episode by setting up their two elderly neighbors Mrs. Baker and Mr. Fillmore so Mrs. Baker will be unavailable to be their babysitter and they can have the one they want, Carrie. It works out for both parties and the couple are still together episodes later. The pair are also played by real-life couple Jean Speegle Howard and Rance Howard, parents of Ron Howard.
• Tom and Diana in Waiting for God, who meet when they're committed to the same retirement home.
• You're Only Young Twice (1971): In "Born Again", Peter discovers he is a year younger than he thought. Following this revelation, he attempts to do everything he couldn't do when he was a vicar, such as getting a girlfriend, the similarly elderly Miss Puffin.

Radio

• Our Miss Brooks: In "Puppy Love, Mr. Barlow and Mrs. Davis", Mrs. Davis falls in love with the aged school custodian. It leads to Face Palm-worthy descriptions of love in old age by callow teenagers Walter Denton and Harriet Conklin.
  • Walter described the old folks' romance as follows:
    Walter: Oh, by the way, how's Mrs. Davis' romance with Mr. Barlow coming along?
    Miss Brooks: Oh, have you noticed that, too? I think it's the cutest thing in the world. Mrs. Davis actually has a bad case of puppy love.
    Walter: It is cute... considering she's in her second puppyhood. No disrespect intended, you understand. After all, what can be more romantic than two lonely old people encountering the grand passion in the sear and yellow leaf of life?
    Miss Brooks: Why, that's absolutely poetic, Walter.
    Walter: The burning desires of youth long past, they look now for the subdued glow of companionship. The warm and simple pleasures that two elderly people in love can share together.
    Miss Brooks: I can see them now - soaking their feet in the same pan of Epsom salts.
  • Later, Harriet ups the ante:
    Miss Brooks: Hello, Harriet. I've got to deliver a message to the custodian. Have you seen him?
    Harriet: Oh, yes. Mr. Barlow just went into his office. (dreamily) Isn't it wonderful, Miss Brooks?
    Miss Brooks: I don't know. I've never been in his office.
    Harriet: I mean about Mr. Barlow and Mrs. Davis. They're crazy about each other. Of course, it's a big secret.
    Miss Brooks: It couldn't be a bigger secret if they took out an ad.
    Harriet: Is there anything more romantic than the mellow romance of old age?
    Miss Brooks: Now please, Harriet.
    Harriet: To think of two people finding love at a time of life when others are preparing to pass on. Two people walking hand in hand in the twilight of life.
    Miss Brooks: Yes, there's nothing like a brisk walk before passing on.

Theater

• In Marshall Karp's Squabbles, Abe and Mildred fall into this trope by the end of the play.

Video Games

• Diner Dash Adventures has Grandpa Norbert courting Grandma Florence.
• Hawke's widowed mother is contemplating finding a Second Love during the second act of Dragon Age II, with the implication that she would seek out this sort of romance. (Leandra is, judging by the ages of her children, only in roughly her fifties; but she describes herself as being "in my dotage," so she sees herself this way.) She does eventually catch the attention of an elderly gentleman who sends her flowers. Unfortunately, he's a Serial Killer and the whole thing ends very badly.
• During the "The Book of Love" quest in The Elder Scrolls V: Skyrim Skyrim, you play the role of matchmaker while observing different kinds of love. At one point, you are tasked with pairing up the fairly old court mage (who might be really old since he's a High Elf) and the Jarl's Housecarl, who looks like she's in her fifties. The priestess of Mara questgiver describes this as a "seasoned" love.
• Implied to be the case with Ellen and Saibara in Harvest Moon: My Little Shop, with Ellen mentioning him on occasion.
• LittleBigPlanet: The second game has Larry Da Vinchi, who is in love with Victoria Von Bathysphere. Larry often refers to Victoria with Affectionate Nickname(s) based on various desserts; befitting that her Laboratory is in a world made of sweets.
• In World Neverland, nothing forces you to get married, so you can get married late in life to another Elderly character if you wish. While NPCs will often get married while young, it is possible for two older characters to get married as well.

Web Comics

• In Alfie (2010), Vera, a late middle-aged Havlin woman and the title character's mother, goes on a journey to find her daughter and hires a guide, an equally middle-aged human named Cillian, to help her. Over the course of their subplot, they slowly but surely form one of these, starting with Belligerent Sexual Tension (mostly on Vera's side), then become Friends with Benefits and finally truly beginning their romance with a Big Damn Kiss.
• in Kevin & Kell, long-divorced Dorothy winds up marrying second husband Douglas (his prior marital status is unknown). They seem to be doing fine when we see them.

Western Animation

• Amphibia: Hop Pop falls in love again with his old crush Sylvia Sundew.
• Avatar: The Last Airbender: While never shown onscreen, it is implied that such is the case between Kanna and Pakku, who do marry. They were in an Arranged Marriage when younger, but Kanna ran away from the Northern Water Tribe since she didn't want to be burdened by their traditions. Pakku was so hurt that he grew into an embittered Straw Misogynist until he met Plucky Girl Katara — Kanna's granddaughter. So it's a mix of this and New Old Flame, strictly speaking.
• DuckTales (1987) features Scrooge McDuck and Glittering Goldie in a Slap-Slap-Kiss relationship, but it's notably sweeter and stabler than their comic counterparts.
• Wanda's dad and Cosmo's mother in The Fairly OddParents!, but it only happens in one episode.
• In Foster's Home for Imaginary Friends episode "Neighbor Pains": It turns out the crotchety Old Man Rivers, who seems resentful of Foster's Home, actually has feelings for Madame Foster. He takes Mac's advice and actually tries talking to her and the two seem to be hitting it off... until they resume fighting at the end of the episode.
• George and Rosemary: George falls in love with Rosemary, his neighbor across the street. George wears dentures. Rosemary has a head full of white hair and a bunch of grandchildren.
• My Little Pony: Friendship Is Magic has the elderly donkey pair of Cranky Doodle Donkey and Matilda. They initially met while young, but an unfortunate case of Poor Communication Kills kept them apart through many years until they reunited, rekindled their romance, and finally married.
• Rugrats has one with Grandpa Lou and his second wife, Lulu — they even got married.
• Grandpa has had these a couple of times on The Simpsons. In one case, Marge tried to hook him up with her widowed mother (then Mr. Burns came along). In another, he dated a woman who lived in the same old folks home who died and left him a large sum of money. Yet another time he dates a cool, rebellious resident of the old folks home who's really just dating him because he's one of the few seniors who can kind-of-sort-of drive. He's currently married to Rita La Fleur, who's roughly the same age as him.

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