Good romantic comedies are genuinely rare. (This comes from someone who has tried to write a couple, and they both flat-out sucked.)
The reason good romantic comedies are rare is because they’re modern-day fairytales, with all that the metaphor implies. Think for a second on the number of terrible revisionist/”original” fairytales you’ve read. (There are a lot.) A great romcom has to have a lot of things: romantic leads you actively want to see together, crackling wit (if it isn’t really funny, you just have a slightly boring romance), and a satisfying ending that avoids being predictable.
This last one is the hardest, because the end goal of most romcoms is to get the boy and the girl together, so either the writer has to avoid that ending altogether (Waitress, Annie Hall), or fake out the audience by suggesting that instead of being a fairytale, this is a “well maybe true love doesn’t always win out, but there are other good things in life so that’s okay” movie and then managing to deliver the happy ending without it being a copout (When Harry Met Sally).
Sometimes a romcom can go a slightly different route and make the relationship secondary to another event. Knocked Up and Juno are both good examples of how to do this, using pregnancy as the arc instead of the romance, which becomes inexorably tied with the pregnancy. For an example of a film that doesn’t do it quite as well: Nine Months. Of course, if you go this route, you don’t really have a pure romcom any more; you’ve got a sort of hybrid. Enjoyable, but not really exemplary of the genre.
(A fourth, rarely used option is to explicitly go with the fairytale aspect of romcoms and deliver the happy ending with a complete lack of irony; this is actually probably the hardest of the four to manage, partly because it’s almost a meta-answer that plays on audience expectations, and partly because you need total audience acceptance of your narrative, which means only a really strong screenplay can dare to pull it off. Think The Princess Bride or Enchanted or Love, Actually.)
The problem is that because of the necessity of a satisfying ending, romantic comedy is a genre with a few dazzling peaks surrounded by mediocrity and outright crap; there really aren’t many B+ level romcoms, I think. You have a few wonderful A+ and As, and then you drop straight to the C+ level (Matthew McConaughey shows up a lot in these sorts of movies), and then it just gets very bad very quickly (Good Luck Chuck, anything by Tyler Perry, et cetera). Which is also the reason guys dismiss a lot of romcoms as chick flicks; way too many romcoms simply pander to basic expectations of the genre, with subpar performances, formulaic plots, and relatively boring comedy. And this isn’t anything new, I might add: there have been shitty romcoms for as long as there have been movies. They weren’t all The Apartment back in the day, you know.
This is a pity, because a really cracking romcom is just about the most satisfying thing going. And Definitely, Maybe, which I have just seen recently, is a really cracking romcom. (See, there was a point to all that meandering introductory crap after all!)
I mention this because I just saw Definitely, Maybe, which instantly makes it into my A+ list. It has the crackling wit (it’s really very funny, with a hilarious supporting appearance by Kevin Kline well worthy of mention) and deftly manages to avoid being predictability by giving the male romantic lead (Ryan Reynolds, who I have always kind of liked anyway, here lowering his natural tendency to overplay lines to a new, appreciated minimum) not one but three potential romantic pairings (Elizabeth Banks, Rachel Weisz and Isla Fisher, all excellent – and, in a medium where there is a pronounced tendency for younger and younger actresses, all stunningly age-appropriate for their roles), in addition to flirting with the possibility that maybe Reynolds doesn’t end up with any of them but instead someone else entirely, and using a terribly clever narrative device to tell the story.
The device is thus: Reynolds is telling his daughter (Abigail Breslin, absolutely goddamned adorable) how he eventually met her mother, whom he is now in the process of divorcing amicably. Over the course of the story, his relationships with each of the women change and vary, making each of them a suitable answer for who he eventually ended up marrying, thus keeping the ending unpredictable (and keeping the chance that this is a “well, at least he has his daughter, whom he clearly adores, and that’s not half bad” ending a fresh possibility throughout). More importantly, it grounds the narrative in sad realism: sometimes things don’t always work out the way you intend, and more often than not relationships don’t arrive fresh out of vacuum-packed storage, but instead are the sum of everything you said and did that came before; a boy does not simply meet, lose, and rewin a girl without (usually) meeting and losing several other girls enroute.
It’s a level of maturity that most romcoms simply don’t possess, and it gives the story a surprising amount of heft for what, in the end, is a fairytale, albeit a dinged and bruised scrappy survivor sort of fairytale. Highly recommended.