First LIN , OMG what you just wrote made me LMAO , i so needed that there were some decent conversations betweem M/D in season 5. So not enough.
And second i do think Maddie was at first taken in by Richard thinking he had money, back then Maddie was always high on people with money, like they were better people to be around, she obviously realizes Richard isnt rich but is a goofy guy. What does she call D/R A couple of nincomepoops? (did i spell that right ?LOL) So dont think she went at all far with him intimately too. Not Maddies style.