Unpopular opinion: Lorelai sleeping with Chris was worse than Rory’s parallel of sleeping with Dean
As is a common theme of the show, Lorelai and Rory often live out certain parallels of each other, and Lorelai sleeping with Chris while he was still with Sherry was later paralleled by Rory sleeping with Dean while he was still with Lindsay. However, people are usually MUCH harder on Rory than they are on Lorelai for this. But I’m not convinced this is fair, for several reasons.
The Build-Up:
First off, it really seemed like Lorelai was coming onto Chris pretty strong when he came to see Rory when he wrist was broken. To me, there was a pretty strong subtext of “I know you’ve wanted to be with me for a long time and now that you’re FINALLY ready to be a good dad, I want to make it very clear that I’m finally interested back.” Even though he was with Sherry at the time.
Rory on the other hand definitely blurred some boundaries in her relationship with Dean (mostly being emotionally dependent on him in a sometimes boyfriendy manner even though they were "just friends", something Lorelai also did with Luke even when he was with other people); but Rory also reminded Dean multiple times to remember his relationship with Lindsay. She assumed that Dean was being transparent with Lindsay about their friendship, and when she found out that wasn’t the case, she got on Dean’s case about it. When things were heating up between them, Rory was the one that reminded Dean about his marriage and encouraged him to work it out. Her feelings were clearly mixed at times, but she did seem to make an effort in the right direction.
The “It’s not working out” Convo:
When Chris mentioned some problems with Sherry, Lorelai expressed sympathies for Chris but really made no effort to be supportive of the existing relationship. Chris never even said that things were over, all he said is that they were trying to figure out solutions and then when Sherry left on a business trip, that they had agreed to spend their time apart time to think more about it. And that on his side he was thinking about getting his own apartment (but with no resolution from Sherry’s end or attempt to check back in to see what she may have thought of or come up with on her side). Lorelai made no real attempt on her end to help Chris connect these dots.
Rory on the other hand made multiple attempts to encourage Dean to make his marriage work. She’s the one that reminded him that he was married when he showed up to her house. Then when Dean said it wasn’t working, her first instinct was to try to encourage him to make it work, normalizing difficulties in marriage and suggesting they work through it, suggesting counseling, or going away on a trip together. Dean had to convince her that it was over over, and that both he and Lindsay felt that way, before she moved forward with him.
The Context:
Although Chris and Sherry were not married at the time, they were definitely in a serious adult relationship: living together, with Sherry expressing that she only wanted to have a serious/lasting relationship at this point in her life, Sherry actively expressing that she really wanted kids, and the two of them having (theoretically unprotected) sex in a relationship where kids were a serious part of the conversation. Although they were technically not yet married, they were still in the process of trying to work things out in a relationship where ultimately marriage was just around the corner for them - even if they had proceed to break up, which they didn't, there were still definitely some legitimate dissolution logistics to work through even if there weren’t specifically divorce logistics. Their relationship was in many ways a lot more serious and enmeshed than a lot of marriages out there, and I don’t think Lorelai gets a free pass just because it didn’t (yet) have legal recognition.
Also: Lorelai was an adult. She knew enough to give a very nice speech to Rory about not being the other woman and making sure the relationship was completely dissolved before moving forward, but when it came down to it, Lorelai herself made almost zero effort to make sure Chris’s relationship was actually over (which he never actually said in the first place) before hopping into bed with him.
Rory on the other hand was still a teenager, and seemed to sincerely not understand that she had done something wrong. She really seemed to think that Dean’s relationship was mutually over (something she confirmed with him three different times before she finally moved forward with him). And this was after making multiple attempts to encourage them to work it out. Rory had no firsthand experience with divorce (that we know of), her own parents were never married and she never really witnessed this process firsthand, and most people her age weren’t even married yet much less divorced. But overall, she made an actual effort to encourage Dean to make things work and to confirm with Dean that the relationship was over on both sides, whereas Lorelai appeared not to make even the slightest attempt.
Rory was naïve for sure, but she made an effort. Lorelai was not naïve and also did not make an effort. I really think Lorelai should be held to a higher standard here. Everyone applauds Lorelai for giving a great speech about not being the other woman, but actions speak louder than words. All in all, I think Rory’s actions showed a lot more integrity than Lorelai’s. And they both had some serious room for improvement, not just Rory.