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A 2008 Romantic Comedy written and directed by Adam Brooks, and starring Ryan Reynolds, Elizabeth Banks, Isla Fisher, and Rachel Weisz. Reynolds plays Will Hayes, a divorced 38 year old father. His 10 year old daughter Maya (Abigail Breslin), lives with her mother but visits him twice a week. On one of these visits, after her first sex education class at school, Maya asks him to recount the story of how he and her mother met, and though initially reluctant to do so, he eventually relents and agrees to tell her the story, on the condition that he be allowed to change the names and some of the facts. The rest of the movie consists of flashbacks to Will's single life, and his relationships with three different women, his college fiancee Emily (Banks), his coworker April (Fisher), and magazine writer Summer (Weisz), intercut by occasional questions and commentary from Maya in the present. It is left to Maya (and the audience) to try and figure out which of the three Will ended up with, and thus which of the three is Maya's mother.

The story begins in 1992 when Will, having just graduated college as an idealistic young aspiring politician, moves from Wisconsin to New York City to work for Bill Clinton's presidential campaign along with his best friend Russell (Derek Luke). The initial plan is for Emily to join him after a few months, at which time he intends to propose, but things don't go according to plan and Will ends up going through several relationships and years of of romantic highs and lows before he finally meets the woman he eventually marries.

The movie received positive reviews from critics, who noted its realistic portrayal of modern relationships and nuanced characters; unlike in most romantic comedies, there's no clear "good" or "bad" love interest, and whom to root for is left up to the audience.

This film contains examples of the following tropes:

  • Affectionate Gesture to the Head: Recognising the gesture is how Maya works out which of the women in the story is her mother.
  • Big Applesauce: Though Will is from Wisconsin, almost the entire movie takes place in New York.
  • Black Best Friend: Russell, though his race isn't particularly emphasized.
  • Blonde, Brunette, Redhead: There's one of each among the primary love interests - blonde (Emily), brunette (Summer), and redhead (April).
  • Boy Meets Girl: Averted: more realistically, it's boy meets one girl, then another, and then another, and tries (unsuccessfully) to find lasting love with each of them in turn.
  • Break His Heart to Save Him: Emily thinks Will would be better off not tying himself down at a young age, and refuses his marriage proposal. When he insists, she informs him that she cheated on him, and it's suggested she did so to make breaking up with him easier.
  • Cassandra Truth: Charlie jokingly warns Will that he shouldn't leave "Emily" alone with him.
  • Cheerful Child: Maya is very cheerful and understanding for a 10 year old, despite the fact that her father tells her some rather sordid and unhappy details about his past life.
  • Comic Role Play: Will practices his proposal speech with April standing in for Emily. The speech:

  Will: "Will you, um, marry me?"

  • Disposable Fiance: Subverted.
  • Divorce Is Temporary: Thankfully averted. Maya eventually accepts that her parents aren't the OTP.
  • Drowning My Sorrows: Will starts to drink heavily after finding out that April is dating a new guy at one point.
  • Earn Your Happy Ending: After Will has been divorced by Sarah (Emily), it's suggested at the end that he may get together with April, after much heartache and years of not even speaking to each other.
  • Eureka Moment: Maya, when she figures out that Emily Sarah is her mother.
  • First Father Wins
  • First Girl Wins: Maya's mother ends up being Emily, with whom Will once again gets together after years apart. Subverted in that the two are now divorced.
  • Framing Device
  • Genre Savvy: Maya has been watching way too many Chick Flicks.
  • Girl-On-Girl Is Hot: At one point Will and Russell discuss this after coming across a description of a lesbian kiss in Emily's diary.
  • Grey and Grey Morality: Unlike in most romantic comedies, none of the characters is entirely saintly or entirely psychotic in their relationships - they're all flawed but well-meaning people trying to figure out what's best for themselves.
  • Happily Ever After: Subverted. One of the first things the audience learns is that Will is being divorced by the woman he married.
  • Heroes Want Redheads: Will seems to prefer April to the other two.
  • Hot Scoop: Summer, played by Rachel Weisz.
  • How We Got Here: The framing device of the movie.
  • In Medias Res: Sort of. The movie is a subversion of the typical romantic comedy plotline in that there is no neat resolution to Will's pursuit of love at the end.
  • Intrepid Reporter: Summer.
  • Ironic Echo: "We've all gotta make copies sometime; your time is now" "Oh, very funny. You're really funny! What a dick."
  • Kavorka Man: Summer's journalism professor, Hampton Roth, who despite being nearly sixty is quite popular with female graduate students.
  • Last Girl Wins: It's implied Will may in the end get together with April, the last of the three he met, though given their past the relationship is by no means a sure thing.
  • Long-Distance Relationship: Will and Emily, initially.
  • Love Hurts: At times.
  • Manic Pixie Dream Girl: April, sorta, though it's strongly and repeatedly subverted. Summer also has elements of the character type.
  • Meet Cute: With April.
  • Memento MacGuffin: April is searching for a copy of Jane Eyre that was given to her by her late father shortly before he died, which plays a rather important role in the plot.
  • Narrative Profanity Filter: As a Call Back to the explanation that casual sex is "rehearsing" for making babies, it's implied that Will's been using that word a fair bit in his relation of the story;

  Maya: I can't believe Emily rehearsed with Charlie!

  • No Ending: At the end of the movie, Will finally gets together with April. Or maybe not. It's definitely implied that they reconcile as friends, but beyond that, it's left ambiguous.
  • Official Couple: Soundly averted.
  • The Reveal: Eventually, the viewer finds out which of the three women Will married.
  • Romantic Comedy: Though it subverts or deconstructs most of the typical tropes.
  • Romantic False Lead: There are several characters who would fit this role in a conventional romantic comedy, but it's consistently subverted as there is no Official Couple and they are generally (and realistically) just portrayed as other fish in the dating pool, not as obstacles to true love.
  • Sleazy Politician: Will's first major client, Arthur Robredo, a candidate to be governor of New York. Will also ends up feeling this way about Bill Clinton.
  • Title Drop: April pretends to be Emily to help Will rehearse his proposal speech at one point - it's her reply when he asks her to marry him.
  • Triang Relations: A couple different variations occur between different characters at different points.
  • Truth in Television: The movie received much praise for its realistic portrayal of modern relationships.
  • Tying Up Romantic Loose Ends: Either subverted or averted entirely, depending on the character.
  • UST: Mostly between Will and April, the only one of the three with whom Will doesn't have a romantic relationship at some point.
  • Wide-Eyed Idealist: Will is at first, about both love and politics.
  • Your Cheating Heart: Precipitates one of Will's breakups at one point.
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