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Anime and Manga
- Maison Ikkoku, essentially the main plot. A young man who's trying to sort his life falls for his beautiful landlady, who turns out to have been recently widowed...
- Karina from Tiger & Bunny, who has a crush on the widowed lead male Kotetsu, despite him being around twice her age. The scene is from the Grand Finale.
- This is the plot of Natsuyuki Rendezvous in which Hazuki is in love with the widowed Rokka-chan, unfortunately for him her late husband is a very clingy ghost only he can see who promptly tries to get in the way.
- ElfQuest has two very different examples: Clearbrook's husband One-Eye is murdered during a sneak attack, and their old friend Treestump immediately takes care of Clearbrook emotionally during her Heroic B.S.O.D. to make sure she doesn't go insane with grief. When it turns out One-Eye is in a kind of magical coma, Treestump makes sure his friend's soul gets all the closure it needs, and he and Clearbrook gradually become lifemates after One-Eye is put to rest. A second, less conventional example happens when Cutter's family is kidnapped 10000 years into the future (far beyond his own natural lifespan) and he decides to at least keep on living normally for as long as he can. His childhood friends Nightfall and Redlance ask him to become their lovemate and live with them for as long as he wants, because the loneliness would otherwise consume him completely. (Interestingly, Nightfall is the best friend of Cutter's kidnapped lifemate Leetah, and it was thought by the entire tribe that she would end up with Cutter because they were born around the same time. Also interestingly, Nightfall's daughter Tyleet ends up becoming the lifemate of both Treestump's daughter Dewshine and Clearbrook's son Scouter.)
- The Sin City story A Dame To Kill For has a subplot involving one of the few honest cops in Basin City getting involved in an affair with a recently widowed Femme Fatale. It ends tragically for him and his partner, whom he kills before committing suicide.
- Gender inverted and without actual marriage (even if they were seriously considering it) in the Spider-Man comics. Gwen... named a certain trope and left Peter heartbroken. Enter Mary Jane whom helps him by being a supportive friend and the two become closer. A few years after her death, they share a kiss and begin to contemplate a relationship. Then this being comics, a Gwen clone shows up (and of course he spend a good deal of the arc believing it was genuinely her). The clone eventually helps him realize that his relationship with Gwen was NOT as perfect as he thought, her hatred of his alter ego ran too deep, and it was MJ he really in love with. However, he never really stopped angsting about Gwen, leading MJ to sometimes question if she really was his second choice (it's mostly entirely baseless, and they have never shown to have anything but unconditional love for each other, but the "what if I managed to save her thing" gets dragged out A LOT).
Films — Animated
- The film Bebe's Kids starts with Robin Harris dating the newly widowed Jameeka, but it turns out he bit off more than he could chew, as he ends up babysitting her friend's incredibly rambunctious kids.
Films — Live-Action
- In Finding Neverland, rumors of this arise as a result of all of the time that James Barrie spends with Sylvia Llewelyn Davies (a rather scandalous situation, considering that he is married). The reality is a platonic variation, and Sylvia's mother, Emma, is rather annoyed with James because his attentions are keeping this from legitimately happening to Sylvia.
- The Film of the Book to Flight of the Intruder has a subplot where the main character ends up getting into a relationship with the widow of his bombadier/navigator, who died in the film's opening.
- In Key Largo, Frank with Nora, although it's mostly on her part. Frank is still dealing with the guilt of surviving the war where his friend—Nora's husband—hadn't.
- In Too Many Husbands (1940), when Bill was declared Legally Dead after a boating accident, his business partner Henry helped the widow "in a million little ways," leading her to marry him six months later. This causes awkwardness when Bill returns from being shipwrecked on a Deserted Island.
- In Miracle on 34th Street she's a divorcee, not a widow, but it's the same principle.
- Sarah and Hull's relationship is like this in Pale Rider. Sarah's husband dies before the plot begins, but it's implied that she's the "loved her husband dearly" variety of widow.
- The Magnificent Ambersons is about a (grown-up) Spoiled Brat with Mommy Issues who is horrified that his widowed mother is falling for her Childhood Sweetheart. Everyone else thinks he's making a fuss about nothing.
- Edward towards Angela in 7 Faces of Dr. Lao; it takes a little magical assistance from the eponymous wizard for her to finally come around.
- In Enoch Arden, Philip declares his love to Annie after Enoch has been missing for several years. He has to be very patient, as she is reluctant to give up on Enoch, and even when she finally marries him, it is mostly Remarrying for Your Kids at first. (She does finally come to return his feelings, however.)
- Ista in Paladin of Souls, also by Lois McMaster Bujold; also she does a lot of the romancing herself, being the POV character.
- Clive Cussler's The Mediterranean Caper. Dirk Pitt does this with Teri von Till, who is still in mourning for her car-racer husband. It later turns out that she's actually an undercover Federal Bureau of Narcotics agent named Amy, so her story may have been fake.
- Vorkosigan Saga: Miles Vorkosigan's love interest Ekaterin is widowed in Komarr, freeing her up for Miles' courtship in A Civil Campaign. Given the five-to-four male/female ratio on Barrayar, however, he quickly finds that he is not her only suitor. And given the unstable and classified circumstances under which the husband died, Miles finds himself slandered of creating a widow for himself...
- And much earlier, in Barrayar, Count Vidal Vordarian had been courting the recently widowed Princess Kareen as part of his scheme to become Regent for Life for her four year old son Gregor. Emperor Ezar saw through him and arranged for his grandson's regency to be assigned to Lord Aral Vorkosigan instead.
- Somehow subverted in Jorge Amado's novel Dona Flor and Her Two Husbands, where the titular Flor is the widow who is eventually romanced, and who has to learn how to open to love again. Of course, things become more complicated, what with the ghost of her first husband coming back�
- In the Incarnations of Immortality novel "Being a Green Mother," after the stunning Niobe loses her husband, she becomes the immortal Clotho. Some 40 years later, she meets and falls in love again with a different man, many years after his wife also died. He even comments (paraphrased) "It's almost like Fate has been saving you until the time was right."
- Atretes, the hero of As Sure As the Dawn, is an ex-gladiator embittered by a failed Destructive Romance who strikes up a partnership with a widow named Rizpah who had previously adopted the child whom he had thought his previous lover had aborted. Despite hating one another's guts at first, they eventually fall for each other; she pulls him out of his nihilistic cynicism and he is able to help her experience true love for the first time (she was a prostitute as a child and her first husband was a kindly older man for whom she never had romantic feelings).
- Gender inverted in The Silmarillion. Indis loved Finwë from afar even before he married. After he visits her when his first wife dies, she openly declares her love for him.
- Messenger has a sinister version. Mentor trades away his true self to become young and handsome in order to romance Stocktender's recently-widowed wife.
- In David Weber's Empire From the Ashes, Star Marshal Tsien Tao-ling does this for Amanda Givens, who lost her first husband in the battle of Zeta Trianguli Australis and subsequently completely shut down emotionally. Happens in the time gap between The Armageddon Inheritance and Heirs of Empire, meaning the romance is recounted in the narrative of the latter:
Narration: Amanda Tsien feared nothing that lived, but she was also an orphan. She'd been only nine years old when she learned a harsh universe's cruelest weapon could be love... and she'd relearned that lesson when Tamman, her first husband, died at Zeta Trianguli Australis. Colin and Jiltanith had watched helplessly as she hid herself in her duties, sealing herself into an armored shell and investing all the emotion she dared risk in Tamman's son. She'd become an automaton, and there'd been nothing even an emperor could do about it, but Tsien Tao-ling had changed that.
Many of the marshal's personnel feared him. That was wise of them, yet something in Amanda had called out to him, despite her defenses, and the man the newsies called "the Juggernaut" had approached her so gently she hadn't even realized he was doing it until it was too late. Until he'd been inside her armor, holding out his hand to offer her the heart few people believed he had... and she'd taken it.
- A Brother's Price has Jerin with the princesses. Since the former husband was a jerk, the widow status is not much dwelled on, though—it is only important insofar as Trini does not really want to remarry, for fear she could get such a jerk again.
- As they did in Real Life, the heroines of Susan Higginbotham's historical fiction often end up remarrying after their first husband comes to a historically sticky end.
- Patrick Jane of The Mentalist lost both his wife and his daughter when they were brutally murdered by a serial killer, which was kind of his fault. He feels incredibly guilty about it and continues to wear his wedding ring years later, all while bent on revenge. Consequently, any woman attempting to date him in the series falls into this, as he has a lot of issues and is extremely cagey about starting up with anyone new. Eventually he gets past this and starts a relationship with Libson. It ends very, very well.
- In the Doctor Who Series 3 episodes Human Nature/Family of Blood, the humanized Doctor falls in love with a widowed nurse working at the school where he teaches. She remarks at some point that it's not fair how the world expects widows to just disappear after their husbands die.
- In the British thriller series The Last Enemy, Stephen and his brother's widow, Yasim, fall in love. Things get a bit more complicated when it turns out that his brother was Faking the Dead. Not that their marriage was in the best of states beforehand.
- In Single Father Dave and Sarah's burgeoning romance is taut with the presence of Rita's memory and how quickly they seem to have gotten together after her death. Rita was also Sarah's best friend and further complicates things by having a boyfriend at the time when she and Dave first get together.
- Frasier: Martin starts dating the widow of a friend and wonders whether he should feel guilty about it.
- Mary Crawley of Downton Abbey, after Matthew dies. After a short bout of deep depression, she recovers surprisingly quickly.
- Lucrezia Borgia of Borgia is surprisingly distraught after the death of her husband, Alfonso de Calabria. Lucky, her longtime lover (the other Alfonso) is still around to marry.
- Garth Brooks's "That Summer" is made of this trope. It tells the story of a young farmhand hired by a widow who then falls for him.
- The Great Big Sea song "Widow in the Window" is about a young bride who refuses to believe her husband died at sea, much to the disappointment of the narrator, who is in love with her.
- Jaheira in Baldur's Gate II
- BioWare gender-inverts the trope into Romancing the Widower quite a few times across their various games:
- Waaaay too many H-games to count.
- Ramon wanted to do this to Vanessa in The King of Fighters. Never got further than being her Dogged Nice Guy.
- In Mitsumete Knight, this is the scenario of one of the winnable girls, Claire Majoram.
- Looking at the game code reveals that this was going to be an option in The Elder Scrolls V: Skyrim, but was cut. The Dragonborn would be able to romance Jarl Elisif the Fair, whose husband was murdered at the start of the Civil War, but there's no way (without using the developer's console) to reach the romancing dialogue.
- The trope is genderflipped in Fire Emblem Fates if a Female Avatar successfully romances Gunther, a man whose wife and child perished alongside his Doomed Hometown.
- Gender-inverted in Something*Positive by Davan's parents. Fred was a widower who had lost his wife and son, which didn't stop Faye from falling in love with him. Despite harsh criticism from Fred's side of the family, Faye and Fred got married and had children of their own.