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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.

Several people have noted that Definitely, Maybe reminds them of Alta fedeltà (2000) (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) (2006) and I marciapiedi di New York (2001) (2001). Another movie said to be a romantic comedy like Definitely, Maybe is Harry, ti presento Sally... (1989) (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 Sballati d'amore (2005) (2005), Boys & girls - Attenzione: il sesso cambia tutto (2000) (2000), Serendipity - Quando l'amore è magia (2001) (2001), Promesse, promesse (1983) (1983), Elizabethtown (2005) (2005), and La ragazza sul ponte (1999) (The Girl on the Bridge) (1999). Romantic comedies that have also been mentioned include Se solo fosse vero (2005) (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) (2005), in which a woman falls in love with a younger man who also happens to be the son of her psychotherapist, Un meraviglioso batticuore (1987) (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 La storia fantastica (1987) (1987), in which a princess is rescued by her childhood beau when she is forced to marry a nasty prince.

While not a movie, the TV show, How I met your mother (2005-2014), follows a very similar concept. A father telling a story to his kids about how him and their mother met and fell in love.

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.