Despite sounding reasonable, Jackie’s claim that Darlene should have known Ben was over her in The Conners season 4 was not a fair assertion. Of all the relationships chronicled on The Conners, Ben and Darlene’s “on-again, off-again” romance might be the most tumultuous. This is saying something, as the love life of Darlene’s sister Becky has been complicated by both The Conners’ alcoholism plotline and her baby’s father being deported by ICE.
However, despite this, it is Ben and Darlene who have been dating, two-timing, broken up, almost engaged, reunited, and broken up again during their three-season run on The Conners. The duo can’t seem to make up their minds about their potential compatibility as a couple—something that Darlene struggled with in one Conners season 4 episode. However, Jackie’s misrepresentation of Ben’s signals did not help matters.
In The Conners’ “Patriarchs and Goddesses” (season 4, episode 11), after Darlene says Ben told her he no longer wanted to be with someone like her, Jackie sardonically noted that “he left her some clues” to this fact. In short order, she then reels off the evidence that Ben and Darlene’s Conners romance was no more, namely their original break up, Ben's devastating rejection of Darlene’s proposal, and his moving on and dating another woman. The implication was that Darlene should have seen this coming and Ben was always forward and consistent in how he felt about her, but that’s not the whole story.
What Jackie’s rapid rundown fails to address is the part that Ben played in Darlene’s breakup with Nick, which occurred because Darlene’s new beau noted that the two still clearly had feelings for each other. Not only that, but earlier in season 4, Ben walked Darlene down the aisle at Dan and Louise’s wedding on The Conners after their breakup, prompting many fans to assume that a future reunion was likely to be in the cards. While Ben telling Darlene he was looking for “easy” was a pretty explicit affirmation that he is no longer interested in her, she wasn’t wrong for getting mixed messages about their hopes of a romantic reunion (as many viewers did).
Even within the action of “Patriarchs and Goddesses,” Ben’s discomfort with Darlene’s definitive emotional goodbye to him is further evidence that he may still want to get back together. Paradoxically, Ben only seems interested in Darlene when she is dating someone else or had been very clear about getting over him, but he may still want her back. One of The Conners season 4’s biggest problems—outside of not mentioning Roseanne—is this messy relationship, and Jackie’s claim that Ben’s motivations are easy to follow is an attempt at retconning some unclear and inconsistent storytelling on the part of the show. The Conners season 4 could still fix Darlene and Ben’s romance, but telling Darlene (and) fans that Ben's actions have made sense all along won’t help matters.