I also thought the guy from Cleveland, Jack, was not 57 years old. He looked more like 67years old. The idea that a not very attractive 67 (or so) year old guy thought it was appropriate or could possibly lead to a relationship for him to date someone like Marissa, or to be hones,t even Fiona, was pretty delusional. His insistence that he liked her because she was from Cleveland was laughable. It seem more like he wanted to meet beautiful young women for dating or maybe even having sex with than that he had any desire for a long-term relationship. Maybe if he was very sweet and kind and seemed likely to take great care of a woman, someone attractive would fall for him-- but that was hardly the case.
I'm not clear on why Patty hired a new staff-- but despite the entree to television, she seems to have trouble holding into staff. Her first assistant didn't stay with her either. I always found the couple who helped her in recent years to be odd-looking in a rather disconcerting way-- the self-presentation seemed highly idiosyncratic, and not very professional looking. But maybe they were very capable and did a great job-- it's just I wonder what new clients thought when they came around soliciting potential dates for the millionaires.