Yes, not a good look for Jess. It's an unwinnable situation to be in. I'm still not sure why Robby wanted to be in a relationship with her; he should have gone off with Babs. They sure are trying to draw parallels from her relationship with Robby to her relationship with Nick though. She used to "trap" Nick that way too.
Like in "Bad News" after the breakup, she had to keep pressing him about how he "really" felt about their breakup and she was upset that he wasn't more upset about the breakup. That's kind of a *beep* thing to do; why would she assume he's not hurting? She's his ex so he wouldn't exactly want to talk all those feelings out with her right then. Geez, at least give him a couple of days. Awfully selfish and myopic of her.
Also, I know "Clean Break" is a highly rated episode, but I was always annoyed that Jess kept pressing Nick about still being attracted to her. "I can't think of anything" was his way of telling her to drop it. They weren't in a relationship so it shouldn't matter if he's attracted to her or not. It was a *beep* thing to do to him to basically force him to tell her she's attractive. He obviously wasn't going to tell her he was still attracted to her because it wouldn't have led anywhere and probably just make things awkward between them.
I would like to say the character has grown up, but the writers have made her really unlikeable at various points of the show.
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