"How was I supposed to plan for fucking forgiveness?" Michael screamed, breaking the glass on a medicine cabinet's mirror, where he had jumped into some sorry bastard who took 20 different prescriptions.
Lucifer, who had reluctantly jumped into the sorry bastard's wife, didn't answer. It was a rhetorical question.
After that, they tried many different things.
They tried age differences. When Dean was an older man, Sam was a younger man. Sam was the young man who went to sit with Dean in the hospital and read to him while he took chemotherapy treatments. (The cancer was to make Dean too weak to fight for Sam; it hadn't worked).
When Dean was an older man and Sam was a teenager, Dean saw Sam living downtown while he was in on a business trip. When Sam was an older man and Dean was a younger man, Dean gave him a kidney (a kidney, they couldn't believe it) and they talked.
When Michael and Lucifer put them on opposite sides of the country, Dean took a road trip and found Sam hitchhiking in the rain and gave him a ride.
When Dean was a woman and Sam was a man, they found their way to each other. When San was a woman and Dean was a man, they found their way to each other. When they were both women, they found their way to each other.
What they needed was total strangers, artificially injected in the timelines they were given, without sacrificing the personalities and the bloodlines that were so hard-wired into each of them.
It didn't matter. Each took bullets, lost their lives and dedicated themselves to the protection of the other, every single time.
No matter how hard they tried, how far apart they put them, no matter what culture they put them in, no matter what ethnic background they gave them, no matter how unlikely or heinous they made the circumstances of them meeting…
The Winchesters found their way to each other.