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Anime & Manga
- The Yuri manga The Structural Formula of First Love by Shuninta Amano is about a lesbian whose high school love dumped her for a guy, but her daughter from him fell in love with the protagonist, in turn. It wasn't entirely intentional, however.
- Kare Kano: Yukino and Arima's eldest daughter, Sakura, falls for Arima's best friend Asaba who has mentioned before that he would marry either, if given the choice.
- ½ Prince: With Gui and Lan happily married, Zhuo is left to pine for Lan. Well, a good sixteen years later no more, as he gets (forcefully) engaged to LanLan, their daughter.
- An old EC Comics science fiction story had an astronaut testing a new spaceship. He returns home to find that decades have passed, despite his only having experienced a short time away. His girlfriend, thinking he was dead, married his best friend, and they're both old now. But their daughter is now a beautiful young woman. The hero falls in love with her and they marry.
- In Sharknado, protagonist Fin is pursued by his younger employee, Nova, though he clearly is carrying a torch for his ex-wife, April. At the end he and April reconcile (a whole six hours after her boyfriend dies!), and while it's not clear, it seems Nova is going to hook up with their son Matt, who is closer to her age.
- In Twilight, Bella and Edward end up together, but leave poor Jacob alone. Not to worry, when their daughter Renesmee is born he "imprints" upon her, essentially becoming romantically bonded for life with an infant.
- In Anne McCaffrey's Tower and the Hive books, the Rowan/Afra/Jeff triangle gets resolved in favour of Rowan/Jeff, and Afra is subsequently paired with their daughter Damia.
- A Song of Ice and Fire has Litterfinger developing an ever-creepy crush on the daughter of his childhood sweetheart. Please note, however, that is it acknowledged as creepy and not reciprocated.
Live Action TV
- A very weird one occurs in Doctor Who. Amy has Rory and the Doctor as potential love interests, and chooses Rory. The Doctor may or may not have some romantic interest in her, and he also may fancy Rory just a little bit — enough to kiss him once, at least. (Rory, for his part, is completely Amy-sexual.) Amy and Rory have a daughter, River, who grows up to marry the Doctor. It's severely complicated by the fact that while they are all time travellers, they are not all necessarily travelling in the same direction or at the same speed. The Doctor meets River before he meets Amy and Rory, on the day River dies, and likes her before anyone except River knows who her parents are. River decided, when she was a kid, to grow up together with her parents at the same age as them, never telling them who she was. Oh, and River has another mother — the Doctor's Bond Creature, eternal Love Interest and wife, the TARDIS.
- Variation in the original V (1983) where Robin Maxwell loved Kyle Bates, but he ended up with her rapidly grown child Elizabeth instead (although there was never a triangle in the first generation).
- In The Sims, this is a very common player tactic. See two sims you think look cool? Marry one now, have your kids grow up with birthday cake and marry the other.
- It is possible for Robin to marry one of the children characters in Fire Emblem Awakening. Robin's child, Morgan, will then not be available until rather late in the game... but will eventually grow up even stronger than usual, having inherited the stat bonuses of not two, but three original-generation parents.
- The same applies to Corrin in Fire Emblem Fates.
- On The Cleveland Show, Rallo has a Precocious Crush on his stepbrother Junior's Girl of the Week, Chanel. Eventually we find out that Chanel and her ex-boyfriend have a daughter together, and Rallo is instantly smitten with her instead. Played With, however, because Junior doesn't wind up with Chanel, instead encouraging her to get back together with her ex-boyfriend for the sake of their daughter.
- Corvax's Evil Plan in Muzzy Comes Back. Since he couldn't get Princess Sylvia in the first movie, he kidnaps her daughter Amanda instead, to raise her as his future wife and queen.
- Bojack Horseman has BoJack attempt to reconnect with an old friend of his only to find out that's shes married with kids. And while even he's not sure if he was actually going to go through with it, he gets dangerously close to having sex with her teenage daughter, essentially destroying the friendship he had for good.