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The following FAQ entries may contain spoilers. Only the biggest ones (if any) will be covered with spoiler tags. Spoiler tags are used sparingly in order to make the page more readable.
For detailed information about the amounts and types of (a) sex and nudity, (b) violence and gore, (c) profanity, (d) alcohol, drugs, and smoking, and (e) frightening and intense scenes in this movie, consult the IMDb Parents Guide for this movie. The Parents Guide for Definitely, Maybe can be found here.
Throughout the movie, Will goes back and forth between three women thinking he is definitely, well, maybe in love with each of them. Also, at one point, he tells one woman how he is going to propose to another one, and when he asks, "Will you marry me?" She answers, "Definitely, maybe."
Will changed the names of his ex-girlfriends in order to protect their identities and to keep Maya guessing. Obviously Maya knows her own mother's name, so by changing the names, she had a harder time figuring out which woman her mother was. Emily's real name was Sarah, Summer's real name was Natasha, and April's name was the only one not changed.
In the end, Will ends up with April.
Several people have noted that Definitely, Maybe reminds them of High Fidelity (2000), in which a 30-something record store owner examines his failed relationships after he is ditched by his last girlfriend. Two other movies that feature young couples and their friends struggling with issues of relationships and commitment include The Last Kiss (2006) and Sidewalks of New York (2001). Another movie said to be a romantic comedy like Definitely, Maybe is When Harry Met Sally... (1989), in which two platonic friends keep bumping into each other over the years. Other movies in which two people meet and separate but bump into each other again include A Lot Like Love (2005), Boys and Girls (2000), Serendipity (2001), Baby It's You (1983), Elizabethtown (2005), and La fille sur le pont (The Girl on the Bridge) (1999). Romantic comedies that have also been mentioned include Just Like Heaven (2005), in which a landscape architect is haunted by the spirit of a woman who used to live in his apartment and is now lying in the hospital in a coma, Prime (2005), in which a woman falls in love with a younger man who also happens to be the son of her psychotherapist, Some Kind of Wonderful (1987), in which a teenage girl realizes that she has feelings for her best friend when he starts to date the most popular girl in school, and The Princess Bride (1987), in which a princess is rescued by her childhood beau when she is forced to marry a nasty prince.
Only one song by Nirvana is heard in the movie, it is called "Come As You Are".
The song is heard twice throughout the movie. Once when Will is at April's apartment, and then again when April tells Will to get off her porch. The rest of the songs and their corresponding scenes can be found here.
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