Definitely, Maybe is a surprisingly rewarding romantic comedy. Imagine, really, old-school Woody Allen starring that shit-eating smirker from Van Wilder, Ryan Reynolds; if this isn’t exactly Annie Hall or Manhattan, the mere fact that it aspires to those heights is worth a celebration of some kind—say, a small street fair in Hoboken?

The film’s told almost entirely in flashback—during that long-lost decade of the 1990s. When first we meet Reynolds in 2008, he’s a corner-
office ad exec being served his final divorce papers. Smartly capturing the ease with which we disconnect from the outside world, he slaps on his iPod and struts through a silent Manhattan. He then picks up his daughter Maya (Abigail Breslin), who turns out to be one of those 11-year-olds in movies who sound like their 51-year-old writer-directors (Adam Brooks, in this case) when discussing things like love, sex, and relationships.

Maya wants to know how it all went wrong between her parents, and as a begrudging bedtime tale, Will lays it out for her, changing the names of the women in his life story in order to keep his daughter (and the audience) guessing Mom’s identity. (Sounds like a very special episode of How I Divorced Your Mother.) As Will recounts his life in New York in the early to mid-’90s, he encounters several women with whom he will fall in and out of love—one of whom will become his wife and Maya’s mother. Only, at the end of Will’s story, the parents will be divorced, and Maya will be left with what she calls “a romantic mystery” absent its fairy-tale finale.

But before the unhappy present day, first to the promising yesterdays: It’s 1992, and Will’s a collegiate Young Democrat in Wisconsin dating the old-fashioned Emily (40-Year-Old Virgin‘s do-it-herselfer Elizabeth Banks). Emily refuses to move to New York, where Will’s been hired to work on Bill Clinton’s 1992 campaign. There, he meets Isla Fisher’s April, the freewheeling Xerox girl with the Smiths T-shirt, and an old friend of Emily’s named Summer (Rachel Weisz), a would-be writer shacked up with a chain-smoking, Scotch-drinking, pop-culture-loathing author-professor brilliantly named Hampton Roth, played by Kevin Kline.

Over the course of the next couple of hours, Will and these bright, beautiful women keep crossing paths—as lovers, as disappointments, as what-coulda-beens, as what-might-bes. Brooks, whose French Kiss screenplay was as tony and old-fashioned a romance as Hollywood’s made in 20 years, ultimately grounds the movie in the everyday. As sweet and silly as the film can get, ultimately it just shrugs and says, “Do your best, expect the worst, you’ll muddle through.”

Of course, one could easily look at the movie as a well-timed portrait of one man’s shattered affection for Bill Clinton—it encompasses his entire presidency, from the early Man From Hope to Monica Lewinsky. Reynolds, muting his smart-ass qualities without dulling his timing, bemoans Clinton’s parsing of words: “What happens when they give him a hard word?” he snaps at the TV as Clinton ponders the meaning of “is.” Truth is, it’s an unexpected delight to find Reynolds in something resembling a grown-up comedy; he forever seemed destined to be the dude from Two Girls, a Guy and a Pizza Place. Maybe he’s no longer a could-have-been, but rather a might-be-after-all.