He hasn't been trying terribly hard. There was a time after he had Cas wipe Lis and Ben's memories that he tried to drown that pain out with other women. It never worked, but it was better than being lonely. After Amara...he's not sure what the change is, but hook-ups are a lot less satisfying and not nearly worth the effort to make them happen. Of course, the 'dad bod' comment had been a blow to his ego, but he probably shouldn't have been hitting on twenty-somethings either.

Obviously, Dean doesn't talk about his feelings and emotions often. While he might not have talked about Lisa to Sam, he had thought about her. It wasn't so much in a still in love way as it was in a cautionary way. Lisa and Cassie were both proof that Dean wasn't cut out for a relationship. As he'd gotten closer to Jo and his feelings had deepened, he'd started to consider if maybe Cassie and Lisa weren't suited to a relationship with him because of their lives and his. Jo was already in this life so maybe it might be okay if he fell in love with her. Dean's eyes narrow at Sam's suggestion and he turns it over in his head. "So less a date and more...some time to discuss things?" He's not sure it's the right move, but Sam is the one in a long term relationship. That counts for something.

Oh, Dean would have slept with Jo years ago, but Jo has always insisted that she had some self-respect and she was not diving into that until he had gotten his shit together. Dean considers the suggestion to hang out. It might be surprising to Sam, but he actually considers some of the things that Sam and Ruby do together. "Like here, with a movie? Or take her out somewhere?"