There were some strong guest stars that had those multiple episode "arcs". If I were advising Jack I would urge him to get back with Julianne Moore.
The Boston accent aside.
I loved him with CC. Second best would be Elisa. I think he had the most believable chemistry with these two ladies.
shareI loved Jack with Nancy.
shareCC or Avery. They were both great for him. I'm not caught up yet so I don't know who he dates next (I am past Avery's kidnapping and it's looking like she doesn't come back), and maybe I'll like the next one even better, but I think these two were excellent matches with Jack.
"Oh my God, where are my manners? Do you wanna try meth?"
I really liked C.C. She was really a good mix of Avery and Nancy, I think. Super ambitious and career focused. But also pretty down to earth and normal. Both interacted with Liz very well too.
But I actually think they did a great job with his love interests. They were all people Jack would be interested in. And fit the facets of his personality. Poor kid who worked his way up so he connects with people like Nancy and Elise. But a rich unapologetic conservative who definitely identifies with the 1% so he fits with Avery and Bianca. Super ambitious and career focused so he gets CC (and again Avery).
Believe me I wish you weren't such a Houston foreclosure of a human being.