Later in the season, in an attempt to throw Sam off of Benny's trail, Dean sends Sam back to Texas, where he and Amelia reconnect.

Who does Sam end up with?

Between the two Winchesters, it was Sam that managed to live a long life until dying from old age. Throughout the epilogue for Sam, he got the apple pie life with a wife and a son named Dean Winchester Jr.

Why did Sam and Amelia break up?

Amelia and Sam moved in together and she even introduced him to her father, who was rather cold toward Sam at first, but eventually warmed up to him. Unfortunately, Amelia learned that her husband Don was in fact alive and, after learning that Don was a good man, Sam broke up with her to give her a chance with him.