Jo hadn't thought of the fact that looking directly into Harry's eyes could cause trouble meant that looking directly into Molly's eyes could have a similar effect. And she really hadn't made the leap that being in Molly's body, with Molly's abilities meant that she shouldn't be looking anyone directly in the eyes too.
So she held Dean's gaze and opened her mouth to say something that would convince him that she actually was Jo when the room started to fade from her vision. Music filtered in from somewhere, though Jo couldn't see the source. With the music came a sort of... well, it was a lot more intense than a movie montage, but a montage of images and feelings.
Carry on my wayward son, For there'll be peace when you are done Lay your weary head to rest Now don't you cry no more
A young boy that Jo knew had to be Dean hugged a blonde woman. Mary. It had to be.
Then Mary was pinned to the ceiling while a nursery burned around her. Dean carried out a baby-Sam. John leaned over him.
"Take care of him."
John's words echoed even as Sam and John shouted at each other and Sam stormed out of a room.
The song shifted and then it was just Dean and John, side by side in the Impala.
Well, life's like a road that you travel on There's one day here and the next day gone Sometimes you bend, sometimes you stand Sometimes you turn your back to the wind
As the father and son drove on, Jo saw various flashes of the creatures they'd hunted. Nothing that lurked in the darkness was safe once the Winchesters had set their sights on it.
Eventually, Dean took John's place in the driver's seat, with Sam at his side.
"Take care of him," John's voice repeated.
The car was surrounded by crushing darkness, and Jo felt the hopelessness crushing in on them.
"If you can't save him, you'll have to kill him," John's voice whispered.
A man with yellow eyes came into view out of the dark, a trail of people about Sam's age behind him. As they closed in on Dean, Sam, and the Impala, one of them stepped forward and stabbed Sam in the back.
Dean caught Sam, and the scene shifted to Sam's body. To Bobby standing over it, telling Dean it's time to bury Sam.
The scene shifted again and now it was Dean and a gorgeous brunette.
"Yeah. Following in Daddy's footsteps. You wanna make a deal. Little Sammy back from the dead, and--let me guess-- you're offering up your own soul? "
After bartering down to one year, Dean kissed the demon.
Dean and Sam were in the Impala again, singing along to 'Dead or Alive'.
Then there were hellhounds. Big and black and vicious and headed for Dean.
There was hellfire and pain, and Dean's screams pierced the air. He was strung up on the torture rack, while a creepy demon leered at him. Every day, it was the same offer. Become the torturer and escape torture. Every day, the same answer.
Until the day when the answer was yes.
The look on Dean's face as the demon-Alistair-handed him a knife was filled with hate, with a willingness to deal out some of the pain that he'd been dealt.