Premarital sex, changing social mores, and fantastical premises probably aren't real obstacles to making good romantic comedies. But Hollywood's fecklessness probably is.
Probably my favorite modernish rom com is Say Anything. A big part of what's great about the film is that writer/director Cameron Crowe manages to create a plot in which the young lead characters, Lloyd Dobler (John Cusack) and Diane Court (Ione Skye), are not assholes. Crowe does this in large part by turning Diane's father Jim (John Mahoney) into the film's main antagonist. It's Jim who keeps the lovers apart; it's Jim who provides the barrier to their love. As a result, Lloyd doesn't have to cheat on Diane, and Diane doesn't have to keep mooning after him even though he treats her like crap. You can fall in love with both of them without feeling dirty—which, surely, is the entire point of a romantic comedy.
On the one hand, then, Say Anything seems to confirm many of the points Christopher Orr makes in his recent Atlantic piece about the dreadfulness of recent rom coms. Orr argues that romantic comedies these days are so bad because it's harder and harder to find a convincing "obstacle to nuptial bliss." Class, profession, race, parental disapproval—none of these, Orr says, are any longer realistic bars to happiness. Romance must have either serious dilemmas like illness—which ditches the comedy—or else hyperbolically ridiculous ones, which make for bad storytelling. Or (as an alternative Orr does not specifically address) it must keep the protagonists separate by turning one or the other or both into horrible people, which makes the ending repulsive rather than satisfying. (Does anyone think that Eddie Murphy's character getting the girl in Boomerang was a happy ending? Anyone?)
But if Say Anything in part confirms Orr's thesis, it also calls it into question. It's certainly true that the '80s were a while ago, but has the ideology of true love actually changed all that much? Is it really more difficult now to imagine a protective father with an honor student daughter being leery of an intellectually and economically downmarket suitor? When I watched it recently, Say Anything didn't seem like a quaint relic of some past time when parents were nervous about their kids dating. Parents are still nervous about their kids dating, surely. If you could have a romantic comedy about that in 1989, you could have a romantic comedy about it now (albeit with more cell phones).
You could argue that Say Anything is only workable because its protagonists are young, and that romance for older people, at least, has become freer and less constrained. The available statistics, don't support that line of thinking, though. A 2010 study found that between 1967 and 2005 high-earning individuals in the US became more, not less, likely to marry other high earners, and low earners became more likely to marry low earners. A 2005 study found that the likelihood of individuals marrying someone with similar educational achievement increased between 1960 and 2003. The trend is similar in Britain (a sometimes source of rom coms). For those born in 1970, 45 percent married into the same class; for those born between 1976 and 1981, that number increased to 56 percent. When you add in growing income inequality generally, it seems clear that we've become less, not more, equal, and that dating patterns reflect that. It's true that barriers to interracial marriage are collapsing—but how many lasting rom coms about interracial dating outside of Guess Who's Coming to Dinner have been made anyways? If anything, you'd think that the lowering of the taboo would open the possibility for the movies to present interracial differences as humorous barriers to be overcome, rather than (a la Jungle Fever) as serious issues to be addressed in problem films.
In addition to the demographic data, there's another bit of evidence that undermines the thesis that society has rendered rom coms obsolete: rom coms themselves. Not Hollywood rom coms, but rom coms in other media. The long-running television mystery/rom-com Bones, for example, derives its frisson from the social and intellectual differences between its brainy anthropologist female lead and its regular-guy FBI agent male lead. Similarly, the Big Bang Theory's romantic tension is built around the intellectual/class differences between geeky physicist and middle American cocktail waitress—which doesn't seem all that different from the nerdy paleontologist/wealthy goofball pairing in Bringing Up Baby.