Well, I no longer think it's likely they'll end up in bed together-Dora is still so uncomfortable with even being touched by Jim that he'll be lucky if he can get a goodnight peck on the cheek in. It's like Dora's been channeling Hannelore, at least as far as Jim's touch is concerned.
And yeah, his "jokes" aren't helping matters any, he really needs to quit it if he wants a second date. Seems to me he's been out of the dating game a long while, hence his being so bad at it (which stands to reason if he's just coming out of a long-standing marriage).
EDIT: Also, dating before the divorce is declared final may be common, but the way things are going here, if it turns out he wasn't joking about that it may be the final straw that makes Dora run away screaming into the night, never to talk to Jim again.