The Winchesters were a weird Family.
John Winchester was the father of five kids, two boys, and three girls.
Dean, Sam, and Natalie were from his marriage to Mary Winchester.
Kylie and Leanne were both from one-night stands who didn't want them.
Dean practically raised all of his siblings.
when Sam left for college at the age of 20, Dean was left with his sisters.
Toward the end of season one, you'll meet the Singer Family.
Bobby Singer is the father of two girls
Skylynn and Novaleigh are all Bobby has left after his wife died.
[Seasons 1-5]
(I don't own any of the supernatural characters, I only own Natalie, Kylie, Leanne, Skylynn, and Novaleigh)