definitely, maybe (PG-13)
IMDb; Rotten Tomatoes; TV Tropes; Universal; Wikipedia; Working Title Films
Ryan Reynolds plays Will Hayes, who works at an advertising agency (his current job is of no importance, but I mention it to contrast his job in flashbacks). And he's in the middle of getting a divorce. And... wait, I should mention that the movie started charming me very early on, when Will tells us he's found the perfect song to play while he walks from work to school, to pick up his adorable and somewhat precocious daughter, Maya (Abigail Breslin). I love the fact that the first track isn't the one he meant to play. That's just such a nice, realistic touch. But he quickly changes it, and the song he listens to on his mp3 player serves as the movie's opening theme, and we see credits as we also see him walking down the busy sidewalks... some good stuff happens. And I think the very fact that he's listening to an mp3 nicely serves to show us the present, in contrast to most of the movie, which happens before mp3 players. Anyway, when he finally gets to Maya's school, there's a major commotion, as many parents have discovered that their ten-year-old kids had been subjected to an unexpected sex-ed class that day.
So, Abigail talks about what she's learned as they walk back to Will's apartment, and of course she has some questions, which he's not comfortable answering. And later, it seems like the whole sex-ed thing, combined with the fact that her parents are getting divorced, leads her to refuse to go to sleep until her father tells her the story of how he met her mother. (This, naturally, reminds me of the show How I Met Your Mother, except that the whole story is told in the course of one movie, as opposed to however many seasons that show ends up being. And also, it's pretty clear that Maya's mother will be one of three women who are introduced fairly early in the story.) Will is reluctant to tell her the story, but he does so, anyway. (Maya is very convincing.) But of course, Will says he's going to change the names of the characters, so that she won't know right away which woman in the story will turn out to be her mother. (It's the rom-com equivalent of a whodunit.)
I should say that presumably, the movie's present is set around 2008, when the movie came out. Will's story begins in 1992, when he moved from Wisconsin to New York City, to work on Bill Clinton's presidential campaign. (At which point, he got his first cell phone, which was comically large, by modern standards.) I should say, an important part of the movie is convincingly recreating different eras from the recent past (including the dawn of the Internet). Anyway, Will wanted to become a speechwriter, but he started off with a very low-level job, basically a gofer. Oh yeah, and I should say Will wants to be President himself, someday. In the meantime, he's passionate about the candidate he's working for, believing Clinton will affect great change for various groups, like African-Americans and women. However, he meets a woman named April (Isla Fisher), who is in charge of the copy machine. She has no interest in politics whatsoever, and no interest in the campaign or the candidate. So she and Will disagree on certain points, but we could call their first encounter "meet cute," I suppose. And over the course of the film, they'll become friends, though their will be periods when they don't see each other, and sometimes don't even stay in touch.
Oh, I totally forgot to mention something important. Will had a girlfriend in Wisconsin (played by Elizabeth Banks), named Emily (Maya assigned her that name at the start of the story). Will was in love with her, and wanted her to come to New York for a visit, though he never intended to stay there permanently. Anyway, I should also mention that before he went to New York, Emily gave him a small package, which he was supposed to deliver to an old friend of hers, named Summer (Rachel Weisz). He had left Summer a message, but she didn't get back to him. Eventually, Will's roommate, Russell (who also worked on the campaign) convinces him to open the package, which turns out to be a diary Summer had written years ago, which they read. Later, Will goes to Summer's apartment and gives her the diary. He also learns that she's an aspiring writer, who's in a relationship with her thesis advisor, Prof. Hampton Roth (Kevin Kline), who's a famous political writer, himself, I guess.
Anyway... Emily, April, and Summer are the three women with whom Will has relationships, at different times, throughout the flashbacks, which take place over several years. Occasionally Will's story is interrupted by Maya, who has questions, comments, or speculation as to which one her mother will turn out to be. And actually, it seems she's ultimately hoping that telling the story will lead her father to realize he still loves her mother. But it's not exactly your typical cliched story of a kid wanting his or her parents to get back together; the important thing is that Maya wants her father to be happy. Well, as the years go by, we see each of the women moving in and out of his life, occasionally meeting up again, as well as seeing Will's career have its ups and downs. I'm not going to give any details of the relationships with each of the women, and of course I'm not saying who Maya's mother was (though she eventually guesses the truth, near the end of the story). And I'm not spoiling anything about how the movie ends, except to say that there is some pain, and ultimately, joy. And it's just a really sweet, cute, funny, genuinely romantic movie. And still it manages to have lots of touches which are both quirky and realistic. And the characters were all well-developed and likable, so I really cared about them, and about the story, and how everything turns out in the end. And I definitely loved how it ends (no "maybe" about it).