... Among the most fundamental obligations of romantic comedy is that there must be an obstacle to nuptial bliss for the budding couple to overcome. And, put simply, such obstacles are getting harder and harder to come by. They used to lie thick on the ground: parental disapproval, difference in social class, a promise made to another. But society has spent decades busily uprooting any impediment to the marriage of true minds. Love is increasingly presumed—perhaps in Hollywood most of all—to transcend class, profession, faith, age, race, gender, and (on occasion) marital status.
Perhaps the most obvious social constraint that’s fallen by the wayside is also the most significant: the taboo against premarital sex. There was a time when carnal knowledge was the (implied) endpoint of the romantic comedy; today, it’s just as likely to be the opening premise. In 2005’s A Lot Like Love—a dull, joyless rip-off of When Harry Met Sally—Amanda Peet and Ashton Kutcher meet cute by having sex in an airplane lavatory before they’ve spoken a single word to each other. Where’s a film to go when the “happy ending” takes place at the beginning?
Christopher Orr's observations seem accurate enough. Alyssa Rosenberg proposes that Orr, nonetheless, missed an important shift she's seen in romantic comedies. There are still obstacles in a romantic comedy but the obstacles may not be where they used to appear.
But a point I think Orr misses is that the genuinely strong romantic comedies of the last decade or so have ventured inward for obstacles, rather than inventing ludicrous external ones. In romantic comedies as in third-wave feminism, the proliferation of choices has forced protagonists to figure out what they really want, leaving indecision, self-doubt, and even arrested development as rich fodder. [emphasis added]
Part of what made Bridesmaids so wonderful was that Annie Walker (Kristen Wiig) wasn't an essentially perfect woman barred by class or reputation from pursuing true love. She was a self-loathing mess grieving the loss of a relationship and her professional dream who had to fix herself before she was capable of loving someone, rather than overcoming external obstacles to be with someone she already loved. In The 40-Year-Old Virgin, Andy (Steve Carell) had to overcome his deep-seated terror of sex, and of growing up, to be able to form an adult emotional relationship. If romantic comedies have gotten harder to do well, maybe it's actually not because so many barriers to finding love have fallen, but rather because modern love's gotten more difficult, and more difficult to capture.
Love hasn't gotten more difficult at all, and arguably it isn't any more difficult to capture, it may simply be that fewer people are aiming for love as much as they are aiming for chemistry. After all, if modern love is really that different from love as it was understood in the past nobody would keep coming up with film adaptations of Jane Austen novels.