Dean - has a certain... empathy with Jennifer, something I really didn't foresee (I need to watch your movie babe ;;). He really does want to know more about her, her life, what she went through. The whole "mysterious fire" thing pings him hard because that's what... he went through! And the idea of someone else going through that same hell... well, he doesn't like it. Dean also finds her a genuinely fun person to be around, easy on the eyes and not hung up on details, which is Dean's idea of perfection.

Kirk - enjoys the bantering with Jennifer. He doesn't actually mind if she rejected him, he'd still try and hit on her. She's fun and Kirk likes fun people. Just spending time with her would be good enough for him (though makeouts. Makeouts would totally be a plus man).