Lisa Braeden is a woman Dean hooked up with for a weekend. At the time, Lisa was a yoga instructor. Dean described it as a bendy weekend . Lisa apparently described it as the night of her life . Lisa has a son called Ben, which she says it's not Dean's, but Ben looks a lot like Dean, even his personality. Dean confesses that he really loves her and cares about her and Ben. And when Dean pictures his perfect life is with her and the kid Dean, at the end of Season 5 after throwing Lucifer down the hole, goes to the door of Lisa and lives with Lisa for a year before Sam shows his face to Dean again.