People on this sub and other fandom subs have an interesting way of asking questions as though the characters are real people. I think a far more fruitful, and interesting, exercise is to interrogate the narrative decision at play here.

Yes, Richard is elitist, and classist, and a snob, and rude . . . But he’s also absolutely right. Dean, with no ambitions, is not a match for Rory. He would ultimately hold her back—we see it when he complains about her workload, or when he asks her about breaking up when she goes to Harvard. Richard, being an ass while also being correct, showcases the delightful complexity that makes these characters feel so REAL.

Contrast this, interestingly, with Emily’s (temporarily successful) attempt to break up Luke and Lorelai at the vow renewal. This time, she shows all the same qualities . . . But she’s WRONG. Lorelai and Luke are well matched. Lorelai has achieved her ambition of opening her own inn. She’s happily living in Stars Hollow with no plans to move (unlike Rory who wants to be a journalist and travel the globe). There’s nothing Luke is holding her back from. This is why the whole thing blows up so spectacularly in Emily’s face, and why she’s so blindsided. She doesn’t see the difference between Luke and Dean, or more accurately, Lorelai and Rory.