imv It's a variant on the joke where one character says, "I just broke up with my girlfriend!"

Then the well-meaning-but-awkward friend / acerbic parent will say "Well, you're never going to do so well as her again!"

I feel like That 70's Show did this a lot with Eric and Donna's relationship, if you watched that. Sort of a kick the puppy joke, you find someone who's mourning then say something that makes it worse because it's hilariously true.