- All-Star Cast: Ben Affleck, Jennifer Aniston, Drew Barrymore, Scarlett Johansson, Kris Kristofferson, Jennifer Connelly, and retroactively Bradley Cooper and Ginnifer Goodwin.
- Billing Displacement: Gigi is arguably the main character, but Ginnifer Goodwin is billed fifth. This is due to the poster billing the cast in alphabetical order. Jennifer Aniston and Jennifer Connelly both only have about twenty minutes of screen time and are billed before Goodwin.
- The Danza: Ginnifer Goodwin as Gigi.
- Dyeing for Your Art: Bradley Cooper gave himself frosted blond tips for the film.
- Unintentional Period Piece: This film practically a time capsule of what dating was like right before the explosive popularity of smartphones in The New '10s, and with them the rise of dating websites and apps, specifically in Gigi's story.
- Some aspects of the film already looked dated when it came out, given it was shot in 2007. Most of the young cast still had landline phones in their homes, and had work numbers that they gave to dates. The film shows voicemail as the primary communication method, and the existence of text messaging is only briefly mentioned. Mary's rant about being rejected on seven different devices also became dated fairly quickly when smartphones consolidated it down to one for most people.
- This film also came out at the latest possible time anyone was still using MySpace.
Trivia / He's Just Not That Into You