This past Friday I was, er, persuaded to see Definitely, Maybe. I won't endorse it as a good movie but I will say that it significantly exceeded my expectations. Maybe that says more about my expectations than about the movie, but I'll go out on a limb here and say it's not bad. ("I've had this thing as a 'triple sell', and I am upgrading it right here, right now. I think this thing could even go as high as a — 'don't buy'!") If you are in a social situation where you must see one of several recent chick flicks, this is the one to see.
One nice touch was the careful attention to both local color and period detail. The movie is set in New York City in the 1990s, and to me it captured something authentic about that time and place, although in retrospect I find it hard to say exactly what. Call it the accumulation of small details, tugging at long-dormant memories, a barbed net trawling through dark waters teeming with silent fish.
Or maybe I've just been gulled by nostalgia. Whatever. I liked it.
There are some other virtues as well. First, the characters are well-written, well-cast, and well-acted, and therefore the romantic chemistry both works when it needs to, and goes wrong when called for. Second, the plot is, for the romantic comedy genre, atypically unpredictable and grounded. Third, there are some genuine laughs to be had.
Finally, in such a thoroughly Hollywood movie, it's a pleasant surprise to see character arcs where relationship to work appears as more than a shallow gesture or plot device. The lead character Will Hayes (Ryan Reynolds) moves to New York to work on Bill Clinton's 1992 Presidential campaign, and later becomes a political consultant. The evolution of Will's relationship to his career in politics is deftly threaded through the movie and (again, going out on a bit of a limb here) deepens his character in a way that romantic comedies usually do not even bother to attempt. Likewise, two out of the three female leads make career decisions, at different points in the movie, that mark a significant revelation or development w.r.t. their characters.
Romantic comedies typically use career and dedication thereof as window dressing. The only struggle that matters is the struggle to couple. Where career appears, it's usually an inverse MacGuffin: a meaningless object that only matters insofar as it obstructs romantic progress in the second act.
But most people spend at least a third of their adult lives working; the choice of how to spend one's time, energy, and talent is one of the most important life choices one makes. And in one's twenties and early thirties (the typical age of romantic comedy protagonists), one's relationship to work looms particularly large. Work reflects one's ideals and values. In life, work and character are deeply intertwined. I don't want to overstate Definitely, Maybe's case here, because it's not wholly successful, but the fact that it attempts to weave career and character together, with some limited success, seems to me a point in its favor.
Now for the bad. Major weaknesses of the movie include (a) far too much screen time spent on the cloyingly sentimental father/daughter storytelling framing device; (b) far too little development of the Emily character (Elizabeth Banks); (c) the lead never seems quite as devastated by love gone wrong as is called for; and (d) the final scene succumbs to Hollywood's allergy to ambiguity and irresolution, and thereby disappoints when it could have been really good and true.
These are significant flaws, and ultimately this movie can't stand up to the really great modern romantic comedies like Annie Hall or When Harry Met Sally. But, as I've said, it's not bad.
("We had it as a 'don't buy'. Let's bump it up to 'risky'!").