We should maybe talk about Dean’s face when Jody mentioned all the things she had been doing to avoid dealing with her grief. When she mentioned dating and “We know how that worked out..”, the shot cut to Dean and this awkward expression.
The last person Jody dated was Crowley. The last date Jody went on Crowley tried to kill her. Dean is working with Crowley. He’s working with the person who tried to kill Jody..