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Jenny Calendar knows that her days with Rupert Giles are numbered.
She isn't stupid. She's known, from the beginning, that this relationship was going to be merely temporary. No matter how bad, no matter how achingly she wants, more than anything, for it it to work.
There are a variety of factors for how doomed her dating Rupert was going to be. Chief among them is the hunk-shaped vampire of an elephant in the room. Angelus—no, Angel; she knows that he's different than the monster that murdered her ancestors (or is he?)—is a ticking time bomb, ready to explode.
Buffy Summers, meanwhile, is too damn young to be a child soldier, and too damn young to be dating someone in his hundreds. (But, again; she would ruin the fragile peace here—and her cover—if she intervenes. It isn't worth burning bridges for the sake of making a flaming torch. It will light the way, but at what cost? Not a cost she wants to examine.)
Sunnydale is one minor monster or odd magic portal away from yet another end-time shitshow. (Not even her friends on the forums could believe her misfortune. The end is beyond seriously nigh. It's right at her doorstep, constantly. She was bored of a boring life, but Sunnydale's messiness sure felt like an overcorrection...)
As for her? Jenny isn't immune, either, to what will unfold—to the fate that awaits her. After all, her history, her duty towards her clan, weighs upon her. She must do what she must. She wants to tell them, but there's never a good time. Will they understand? Read it as betrayal? Who knows. But, that's an issue for later.
For now, she has Giles, and she's happy.
With England, with his stiff upper lip and his oddly-endearing wrinkles and the way he stammers through sentences and blushes when he's flustered... She can forget, if only for a moment. He's older; around a decade older, at that. But he's nice. There's a darkness there, behind the aloofness. Sometimes, when she watches him look at the kids—his kids, he's caught himself saying, even as he insists that he purely cares about them from a duty perspective, but Jenny knows—there's something else there. He adores those kids, and would die for them.
He also, she realizes, would die for her, if she'd let him. She isn't sure how to feel about this.
So, as she is catching herself, one early January afternoon, leaning against her desk between class periods, Rupert's right arm in the small of her back, his left hand cradling the back of her head, and his lips (slightly chapped) against hers, she knows that it will end one day. She can feel her destiny, twining around them, whispering doubts and insecurities in her ear.
He lets go, eventually, face flushed and sort of breathless, smiling like an idiot, and she smiles back.
For now, she has this delicate, fragile, hopeful love. She will cherish it—and the man before her—with every bit of strength she's got.