- Acclaimed Flop: It only got limited release in its home country, but critics (including Roger Ebert) and audiences who saw it loved it. It eventually became a Cult Classic.
- Actor Allusion: Josh Radnor plays an Ohio native living in New York. The Ohio part doubles as Actor-Shared Background.
- Actor-Shared Background:
- Both Josh Radnor and Allison Janney studied at Kenyon College, the place where the film is shot.
- Much like Zibby, Elizabeth Olsen is also an Arts major.
- Despite the Dawson Casting, Josh Radnor and Elizabeth Olsen have the same age-gap as their characters (15 years to their characters' 16).
- John Magaro is from Akron, Ohio.
- Billing Displacement:
- Kate Burton and Robert Desiderio are billed before Zac Efron. All of their characters have short roles, but Nat has more presence in the story than both of Zibby's parents.
- Kristen Bush is billed before Ali Ahn, Ned Daunis, and Gregg Edelman despite her character only appearing in a single scene near the beginning.
- Completely Different Title:
- Released in Brazil as Love Stories.
- Released in China as Liberal Arts Love Song.
- Released in France as Love and Other Lessons.
- Released in Greece as The Paths of Love.
- Released in Hungary as That's How I Went.
- Released in Hong Kong as Heartsong for a Campus Romance.
- Released in Japan as A Literary Lesson for Two People In Love.
- Released in Russia and Estonia as Humanities.
- Released in Spain and Portugal as Love Letters.
- Released in Taiwan as Compulsory Course of Love.
- Released in Vietnam as The Art of Freedom.
- Copiously Credited Creator: Aside from playing the main lead, Josh Radnor also directed, wrote, and produced the film.
- The Danza:
- Elizabeth Olsen plays Zibby, whose real name is Elizabeth.
- Elizabeth Reaser as Ana, since Reaser's middle name is Ann.
- Dawson Casting: 19 year olds Zibby, Dean, and Vanessa are respectively played by 23 year old Elizabeth Olsen, 29 year old John Magaro, and 31 year old Ali Ahn. The 35 year old Jesse is played by 38 year old Josh Radnor.
- Deleted Role: There's a subplot about Jesse's best friend, played by Michael Weston, who is trying to go overseas that was cut in the theatrical version. It's restored in the DVD version.
- I Want You to Meet an Old Friend of Mine:
- Nat (Zac Efron) and Prof. Fairfield (Allison Janney) definitely know each other.
- Richard Jenkins was also part of Josh Radnor's previous film.
- Kate Burton and Elizabeth Reaser are (or were in Reaser's case) both recurring cast members of Grey's Anatomy.
- Playing Against Type:
- Elizabeth Olsen mainly hopped on board because all her previous films up to this point were Horrors or Psychological Thrillers where she played Broken Birds. Zibby is notably her first (of her eventually few) light-hearted role.
- While Zac Efron has already proven his acting chops by this point, his characters still bank over Efron's Mr. Fanservice status. Nat, while not really bad-looking, is highlighted more through his personality and even wears chullo to downplay Zac's looks.
- Playing with Character Type: Josh Radnor plays Jesse essentially like Ted Mosby (e.g. Nice Guy who's In Love with Love), but more grounded and with maturity.
- Vacation, Dear Boy: At the end of the day, Josh Radnor himself admitted he just wanted a reason to visit his alma mater.
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