Prudence Halliwell wasn't easily terrified. She had grown up under the hard ruling of her headstrong grandmother and fought countless battles against the monster known as Phoebe. At seventeen all Prue wanted to do was let loose and have some fun, which if truth be told she hadn't had in a really long time. There were too many expectations on her plate; go to college and excel, but you can't go away because you have two little sisters depending on you, etc. That was why Prue was taking a break from all of this to have one normal, crazy teenaged experience before it was all over and it had all begun when she ran into Dean Winchester.
He was the new, cool and slightly brooding bad boy who could make you crumble at his hard stony face or melt at his confident half grin. Dean transferred to Baker High in the middle of the semester and there had instantly been this connection when their eyes met. He had walked into the classroom, turned down her row of desks and sat directly behind her. Prue still remembered the way he had smelled like a mechanic, and how for the first time the smell of oil and fumes didn't disgust her.
She and Andy had broken up right before Dean had arrived on the scene and Prue had been a little depressed because it had all come down to the fact that Prue was trapped in San Francisco under her Grams' thumb. It was all too much. Her mother had died, her father abandoned them, she was responsible for a family during her teenage years and there didn't seem to be any hope for her own happiness. Andy had been unwilling to stay for her or to maintain a long distance relationship, and Prue was once again abandoned by the man she had loved with all of her heart.
That first day she had tried to avoid him; giving him her famous ice queen stare that could freeze the hottest of the football players and break them into shards of glass. Dean just gave her his characteristically Dean Winchester grin, like he saw through her. That weekend the two ran into each other at a party and Prue couldn't help but give in and smile at his asinine jokes. Though he hid behind his humor and dumbed himself down, Prue could tell he knew more about the world than he was letting on.
A little too much to drink and a slow dance or two later Prue knew that she needed this, no matter how long it actually lasted. She was finally letting go and having fun and who was getting hurt by it? No one. No one was hurt by her taking some time to enjoy herself. Of course, Grams didn't feel that way when Prue came home two hours after curfew and she was grounded. Dean didn't seem to mind and for the next two weeks he stood under her window, catching her as she snuck out and giving her a boost every time she snuck back in.
They would go to the park and talk and dance but most importantly they would kiss, and god when he kissed her she felt like there was no one else in the world; like they were first man and woman to love in all of creation. Prue thought she knew San Francisco inside and out, and when Dean first took her to Golden Gate Park she was hesitant because that's where her spot was with Andy but Dean had taken her to strawberry hill to sit by the waterfall.
It was there that she finally let someone love her and she returned that love openly, unafraid of the consequences it usually brought. Andy had been her first love but nothing ever happened beyond any heavy making out, and knowing how easily he had allowed her family situation to get between them made her happy that her first time would be with Dean.
Still, over the next couple of weeks Dean spent more and more time helping his dad and watching his little brother Sam. Prue loved that side of Dean and completely understood; they were two halves of a whole and no one else would know what it was she sacrificed like Dean did. He started coming around with more and more cuts and bruises and would only say that he had hit his head while working on a car or he got it wrestling with his brother. As his dad got more and more work around the city Dean was able to spend less and less time with her.
Then it happened. Dean had tried to put together a date with Prue that would show her how much he cared and smooth things over with them until his dad's work was done. He had scored the car for the night and he had taken her to their spot at the waterfalls with food he had gotten from a café not too far from his motel. It had cost him most of his scam money from hustling at pool but Prue was way more important than the skin mags he usually reserved the money for. They were there at the waterfalls, kissing slowly as the lay down in the grass when it came out of nowhere; the demon Dean's dad had been tracking.
Unfortunately, John wasn't the only one with his eyes on this thing and Penny Halliwell showed up to the vanquish. Prue was stuck in the middle, and although Dean did his best to get her out of the way she got hurt. The damage was done and now that the hunt was over he would be moving on and leaving behind the one person who made him feel normal. He never saw her again until he saw her name in the paper while he was investigating the death of a prominent doctor and a young woman at 1329 Prescott street more than ten years later.