Sam & his new bride, Becky head to her place of Pine Creek, Delaware. She goes to where her high school reunion and shows Sam off and signs up to be there. Then she runs into her good friend, Guy (a Wiccan & the event planner of the reunion) and he seems a little surprised to see Sam (like he knows him). Well we finally find out that Becky has been getting a Love Elixir from Guy and she's using it on Sam. She runs out and hits Sam over the head with a pan and drives him to her cabin and ties him to the bed. Poor Sam!
Dean is also there working a job. Apparently there are people dying from freak accidents after having their dreams come true. Dean gets a new partner, a scrawny guy. Eventually they figure out that it's a crossroads demon and somehow he's collecting early and also figure out that Becky made a deal with one.
Actually she didn't, turns out Guy is the crossroads demon and when she goes to get more elixir he tells her that he can make Sam permanently love her and that he'll even give her 25 years. We are left in the dark as to her decision until she traps him and Sam, Dean & Scrawny guy come. Guy found a loophole in the contract and has his intern killing them by accident. Then Crowley comes and says that Guy can't do that because it's bad for business. So he lets all the people that haven't died and made contracts go and he takes Guy to make an example of him. Also he tells them that he hates the Leviathans and he's telling his demons to stay out of the Winchesters' way so they can kill them.
In the end, Sam gets an annulment and he says he'll never see Becky again.