Although Jesse is hardly in a good place for forming a healthy relationship at any point during “Breaking Bad,” his fun-loving, caring nature and desire to provide for those he loves would make him a good partner — if he were able to get his life straightened out. Unfortunately, he never manages to get clean and free of bad influences long enough to find out, and Jesse’s personal demons lead to the tragic loss of not one but two of his girlfriends.
It’s always dodgy when two fragile souls in recovery find each other, and that’s exactly what happens with Jane Margolis, the 18-month sober tattoo artist and landlord he falls deeply in love with. They also fall completely off the wagon together after Jesse loses Combo, a situation that leads to Walter withholding his money until he gets himself straightened out. After the toxic flames concoct a plan to binge-use heroin one last time before moving on to start a new life with money from Walt, Walter finds the overdosed pair passed out and watches silently as Jane chokes to death.
His later relationship with another recovering addict, Andrea Cantillo, ends just as badly. Not long after their relationship is strained due to Jesse’s revelation that he’s cooking meth, Todd kills her in cold blood while a bound and gagged Jesse is forced to watch.
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