Dean Winchester (portrayed by Jensen Ackles) and Lisa Braeden (portrayed by Cindy Sampson) from Supernatural. They have shared a complicated, romantic relationship. They're almost like family, which includes Lisa's son Ben, due to Dean's relationship with the two. Dean deeply cares for Lisa and Ben and would hate to see them hurt. On multiple occasions, Dean has shown that - of all the women he has slept with - he truly loves Lisa. Before and during the first few episodes of, season 6, Dean lives with the Braedens for a full year, he has a monogamous relationship with Lisa and takes on a paternal role with Ben.