Yeah, y'all are probably entitled to shoot me for such a horrendous crack fic. But it was either Adrian/Jill or Adrian/Sydney, and at least Adrian and Jill know each other (as opposed to only knowing about each other) in canon.

I originally wanted this to be an actual one-shot, complete with Adrian meeting Jill, them having sex, and then Dimitri getting a panicked call from Adrian the next morning...

I just made up the prompts, but I did look though several "50 sentences/50 prompts" fics to get inspiration.

#01: Morning After
After waking up and regaining the fuzzy memories from the night before, Adrian had panicked – now that he knew her name, it was hard to think of the woman he'd slept with as anything other than her former fourteen-year-old self.

#02: Note
Jill'd had a funny feeling in her stomach when she left Adrian's room; before they'd lost contact, he had always thought of her as a little sister, and she doubted that he'd want to start a relationship after reading the quick note she'd left in the bathroom.

#03: Smile
Adrian and Jill both had doubts about the seven-year age gap, so they decided to take it slow, starting with secretive smiles and handholding.

#04: Flowers
Lissa had been shocked to hear about the couple – like Adrian, she had always thought of Jill like a little sister, a child – but she soon got over it and even helped Adrian chose appropriate flowers after a particularly bad fight.

#05: Coffee
When she heard about Adrian and Jill, Rose laughed – then she poured her (thankfully lukewarm) coffee all over Adrian and said what sounded like foreign curse words.

#06: Disturbed
Christian was, frankly, a little disturbed when he heard about them.

#07: Graduation
Adrian was happy to see Jill graduate, and happy that she joined Lissa at Lehigh University.

#08: College
He was less happy that she talked him into taking a few classes himself.

#09: Doubt
Emily had some doubts about her daughter dating a man with Adrian's reputation, but she sighed and kept her qualms to herself after she saw how happy they seemed to be together.

#10: Habits
Daniella thought Jill was a little young, but she liked the girl – not only was she a good person, but she was also shaming Adrian into breaking his worst habits (painfully slowly, it was true, but it was happening).

#11: Ring
Adrian knew it would be a long time before he and Jill would think about marriage seriously, but sometimes he couldn't help scrolling though jewelry sites, looking for a nice engagement/wedding ring, when he knew she was asleep or at a class.

#12: Worry
At times, Jill worried that Adrian thought she only loved him because of his money, looks, and/or high place in Moroi society; to combat this, she usually wrote a love note and stuck it on the fridge.

#13: Sketch
One day, while flipping through is sketchbook, Adrian's art teacher ran across an old sketch he'd done of Jill while she slept; when she'd frowned, Adrian thought her dislike of new art students drawing nudes was going to make the old woman knock off points – but instead, she bitched at him for not inking or coloring it.

#14: Dating
It had briefly crossed her mind to date around a bit more before committing herself to Adrian – he was technically the only person she'd seriously dated – but Jill pushed the thought out of her mind; she liked him, but if everything crashed, she would eventually move on.

#15: Name
Jill had never really liked her full name, but whenever Adrian said it, his voice gave the word a special meaning.

#16: Thunder/Lightning
Jill was thankful every time Adrian stayed up with her during thunderstorms, even if he had an early class.

#17: Afterlife
Whenever Adrian wondered about what Tatiana would have said if she could see him and Jill together – or see any part of the life he had – he hoped they would be words of approval.

#18: Dust
At first, it was hard, and Adrian had to constantly distract himself to keep from going outside to smoke – so it came as a shock when Jill remarked one evening that she had actually dusted the pack of cigarettes sitting on his desk.

#19: Animal
As an anniversary present – of course he wasn't a Christmas present, because giving pets as presents was bad – and to celebrate finally buying their own house, Jill and Adrian visited the local pet shelter and picked out the loneliest cat there.

#20: Annoyance
He would never mention it to the man, but whenever Adrian thought about that morning after, he always got a little upset that Dimitri had never answered his phone.