- In The Antithesis, love is a perpetual curse on most characters, whose personalities and ideas of affection become tainted through life experiences pertaining to love. Alezair's love for Leid repeatedly condemns him to fits of rage, insanity and substance abuse, and at one point his devotion for her nearly ends his existence entirely.
- Comes up a lot in Survival of the Fittest because Anyone Can Die (and usually will), the most prominent examples include:
- Bryan Calvert goes through the death of Tori Johnson, whom he'd been protecting for almost the entire game.
- Adam Dodd's girlfriend Amanda Jones is killed in his absence, setting him off on a path of revenge going after her murderer.
- Ricky Callahan similarly safeguards his girlfriend Whitney Acosta for most of v2. When Calvert accidentally kills her, Ricky commits suicide.
- Sean O'Cann, after recently coming out of the closet and engaging in a thoroughly romantic relationship, gets this treatment, with his boyfriend Andy Walker biting the dust not long after the game began. Cruelly, they'd met each other prior to this and become separated, leading to Andy's death.
- Billy (Doctor Horrible) spends the entirety of Dr. Horrible's Sing-Along Blog painfully infatuated with Penny, only for his Arch nemesis Captain Hammer to accidentally kill her while trying to kill Doctor Horrible with his own Death Ray. This was after Captain Hammer dated Penny just to screw with Billy.
- In Happy Tree Friends, being the type of show it is, every single episode featuring a romantic relationship ends in tears (and often, blood as well). The only characters who have survived an episode unharmed and together are Cuddles and Giggles in I Nub You, and they weren't the stars of that episode.
- In Noob, Arthéon has a girlfriend during the entire fourth season. Long story short, Noob is a five-season webseries.
- Whether played for laughs or drama, being in love never works out well for the characters of Red vs. Blue. Emphasized in the later seasons, when Church spends an entire season learning to let go and move on from Tex, York and Carolina's relationship ends before it ever really begins, C.T. dies in the arms of her Insurrectionist boyfriend, and the implication that the events of the whole series happened because the Director never got over his lost love.
- In Everyman HYBRID, no love interest is save from Slendy and later HABIT.
- Firstly, Jessa and Jeff. She disappears shortly after the group starts to encounter Slenderman, which loosens Jeffs grip on sanity considerably.
- Then there is Vin and Lexi. He starts dating her, and when he goes to meet her with Evan, talking about how good he feels with her, they find a thrashed appartement and seemingly, although never directly confirmed, Lexis dead body. Even worse, its subtly implied that Vin killed her himself while under Slendys influence.
- What takes the cake, though, is Evan and Steph. They meet each other only because of Slendy, and after she gets pregnant Evan states that her and the baby were the only good thing to come out of all that. Shortly after, he gets possessed by HABIT, and after Evan learns what he did to Steph and the baby under HABIT's influence he loses the will to live.
- Also Jessie, friend of the group and ex- girlfriend of Evan, gets attacked and killed by the Rake in her own house.
Love Hurts / Web Original