Times where the Love Interest decides that Love Cannot Overcome in Literature.
- At the end of Fifty Shades of Grey, Ana confesses she's in love with Christian, but leaves him because she can't handle his more extreme sexual kinks. However, in the next book she quickly takes him back when he promises to work on himself.
- Alex Delaware: Alex's girlfriend, Robin, eventually breaks up with him due to his work with the police and her fears that he's becoming an adrenaline junkie.
- Alice Adams: The titular Alice Adams pretends to be an incredibly wealthy socialite to court a wealthy suitor that she's hopelessly smitten with. She knows it's only a matter of time before he learns that her father isn't really wealthy, but she hopes that if she puts it off long enough he'll fall for her deeply enough that his love will overcome it. It doesn't.
- The Ballad of Songbirds and Snakes. Coriolanus's love for Lucy Gray isn't strong enough for him to give up his Capitol prejudices or comfortable, privileged life (a Foregone Conclusion, as this is a prequel and the audience already knows he'll become the cruel president Katniss will have to contend with sixty-odd years later). Lucy Gray, meanwhile, won't put her love for him over her inability to trust him and ultimately leaves him before he can leave her.
- The reason behind Marthona and Dalanar's break-up in Earth's Children. Although they loved each other, they amicably ended things because they couldn't reconcile their differences. Though it's never explicitly mentioned what went wrong, it's implied she found him overbearing, whilst he felt she didn't really need him around. They've since moved on with other partners they are better suited to, although some people still tell stories of their 'tragic love', which Marthona finds embarrassing.
- In Every Day, by David Levithan, love doesn't overcome... sorta. The central premise is that A is a genderless being who wakes up each morning in a different person's body. S/he falls for a girl, Rhiannon, but she ultimately can't deal with the stress and difficulty that comes along with such an existence. Then A realizes that there's a chance s/he could just pick one body and stay in it. Ultimately, though, s/he decides that would be totally unethical, and doesn't return to Rhiannon. It is, as you can imagine, a major tearjerker. In the film adaptation, at least, A convinces Rhiannon to date one of her friends, and the next day said friend compliments her.
- Harry Potter: Merope Gaunt is hopelessly in love with Tom Riddle, the local squire, and feeds him love potions so he'll love her back. Eventually she conceives a child with Tom and stops drugging him, believing her love for him and their child will keep them together. Surprise, surprise, it isn't, and she ends up suffering Death by Childbirth in an orphanage to the future Voldemort.
- In the short story book Luscious Spirit Collection, "Ours is a House of Refuge" ends this way. The story revolves around Alice meeting her old flame Tori and the two seemingly coming together again. But after about a month, Alice breaks it off as she realizes Tori still suffers the same ambiguous disorder and self-destructive behavior that drove them apart in the first place. Tori gracefully accepts this, even as Alice admits she can never bring herself to face Tori again and risk doing it all over.
- Middlemarch: When Lydgate and Rosamond have serious money troubles, it fractures their relationship, and Lydgate realizes to his heartbreak that their love for each other isn't strong enough to bear up under the prospect of poverty, much less the real thing. Rosamond's affection for him rapidly cools when they have a real argument and he gainsays her about something important to her. Eventually they recover from being in outright conflict, and Rosamond ultimately avoids cheating on him, but they're never again really in love (and there's a strong sense that the only reason they stay married at all is that it's the 1800s and divorce is the nigh-unthinkable nuclear option).
- She Is The One: Jack and Kayla really, truly love each other, but that alone isn't enough in the face of real life. They both have to work hard to keep their relationship going, sometimes with each other. . . and sometimes against each other. Most of the story's dramatic tension comes from them just trying to juggle their relationship and the demands of high school and then college.
- Dianora has a passage about this in Tigana. She loves Brandin, and she loves her homeland, which he razed. Both of these absolutely break her heart. Try as she might, she can't make herself not love Brandin. And she can't bear to turn her back on Tigana either.But Tigana's ruin lay between the two of them like a chasm in the world. The lesson of her days, Dianora thought, was simply this: that love was not enough. Whatever the songs of the troubadours might say. Whatever hope it might seem to offer, love was simply not enough to bridge the chasm in her world. Which was why she was here, what the riselka's vision in the garden had offered her: an end to the terrible, bottomless divisions in her heart.
- While Tia's marriage to Cedric in The Villainess Lives Again is a clear case of Love Redeems, one of the things she blames herself for throughout the story was marrying her best friend Lisia to her psychopathic brother Laurence. What she doesn't realize is that Lisia actually did love him and tried to change him, but his abusive behavior caused her eventual death. In the new timeline Lisia is still willing to give it a try but when he refuses to run away with her, she gives up. He kidnaps her later, but Lisia herself ends up killing him because there is no fixing Laurence.
- Inverted in the Vorkosigan Saga: Ellie Quinn loves Miles and is perfectly fine with his dangerous life as a mercenary and secret agent; it's the prospect of becoming Lady Vorkosigan and being forced to move to Barryar she can't get past.
- Victor Henry's wife in Winds of War and War and Remembrance.
