Will Hayes wants to explain himself to his daughter. That’s the whole engine of “Definitely, Maybe,” and the movie spends its full running length letting him do exactly that. Ryan Reynolds plays Will, a former political consultant who tells his daughter Maya, played by Abigail Breslin, the story of his three failed marriages. Each ex-wife gets her own chapter, each with a name changed to keep Maya guessing. It’s a simple idea dressed up as a love story, and mostly it works.
The Three Women
The film follows Will’s path through three women, each a disaster in her own way. Elizabeth Banks plays Emily, the college sweetheart he left behind for the Clinton campaign. Isla Fisher is April, the campaign staffer who kisses him but never gets the ending she wanted. Rachel Weisz plays Summer, the married woman he kissed back when she was still with her professor Hampton Roth, played by Kevin Kline. Each relationship ends badly, and each one tells us something about the man Will became.
| Woman | Role in Will’s life | Ending |
|---|---|---|
| Emily | College sweetheart | Leaves him after sleeping with his roommate |
| April | Campaign colleague | Kisses him, then loses him |
| Summer | Journalist | Ends the affair before it starts |
What Works, What Doesn’t
Reynolds carries the film, and he’s the reason it holds together. His performance is warm, funny, and sad enough to earn the emotional weight of the story. The supporting cast is strong across the board, with Banks, Fisher, Weisz, and Kline all giving layered turns. The writing leans on the meta trick of telling a story within a story, and it mostly lands. When Will changes names and dates to protect the innocent, we see exactly why he’s doing it, and that makes the reveal of each woman’s identity feel earned rather than cheap.
The film stumbles when it stretches beyond the intimate scale of Will and Maya. Some of the Clinton-era politics and the consulting firm scenes feel like padding, and the plot occasionally loses focus while chasing its own twist. The tagline promises three disasters and one last chance, and the film delivers on the promise, but not always with the precision it needs.
“Definitely, Maybe” is a modest romance built around a clever conceit. It doesn’t reinvent the genre, but it executes its idea with care and a cast that knows exactly what it’s doing. Reynolds proves he can anchor a lead role, and the film solidifies his status as a reliable leading man. The story is slight, but it’s a pleasant one, told with a light touch and a genuine heart.
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