As much as I wish for Jen and Judy to get together eventually, I actually won't mind very much if Judy explores her relationship with Michelle first.
Jen is in a very special place in Judy's life where she loves Judy to fucking pieces, but she had also hurt her very much in so many ways. Their relationship is actually very complicated.
Michelle though is someone with a relatively uncomplicated life. Even better, she's got very strong boundaries and an even stronger sense of right and wrong. Where Jen regularly (albeit unintentionally) used Judy's submissiveness for her own benefit, Michelle had already shown that she will not tolerate that kind of behavior.
Michelle apologized for Perez when she was rude to Judy. And not only did she apologize for that, she made sure Judy knows she definitely did not deserve Perez's rudeness or accusations.
Should Michelle and Judy get their act together, Michelle is by far the most perfect person to model for Judy what appropriate boundaries look like. Not only does she know what they are, she is also very conscientious in enforcing them.
While people can argue that Jen can so easily do this too, my problem comes with the fact that, by season 2, Jen had cross so many lines, her own relationship with Judy's boundaries have become complicated too. She was arguably almost (but not quite) as bad as Steve in season 2.
Imagine the amount of dysfunction possible if Jen retains her power to set those lines for Judy. Because the fact of the matter was that that was their arrangement and power structure in season 2. Judy did not do anything without Jen's consent. She could not mourn Steve until Jen let her. She let go of Michelle when Jen insisted on that too.
Judy was goddamn lucky Jen was not actually Steve.
My point is that should Michelle be the primary partner, everything we know about her so far indicates that should Judy give Michelle the same power she gave Jen (and Steve) over her, chances are Michelle would say no. Even better, she might even teach Judy what the fuck agency is why Judy should do her best to protect hers instead of just giving it over.
She will not tolerate Judy's "okays" and "sorries". She had already shown during their break up scene that she has very strong opinions about Judy letting other people walk over her. And in the grand scheme of things, that violation was very minor.
Judy's relationships almost eventually fucked up because she couldn't protect herself from people who would use her and hurt her. Michelle would not only refrain from hurting her in the first place, she is also the person in the best position to teach Judy how to protect herself.
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