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Nitpick: In the future, Peter Benedict says that Jack was "Congressman for the 22nd district of Missouri." Missouri currently has nine congressional seats, and would have to have populations comprable to Ohio or Illinois in order to have twenty-two congressmen.
Sloppy editing (repeating text, overlapping sentences) on madeup newspaper articles that were briefly shown.
Grace shows up at the hospital in the hour following the accident at the same time as Missy's father. But Grace was on an overnight field trip with Bobby in Philadelphia. How did could she have gotten back to town so quickly? Bobby's friend Warren is back in town the very next morning, when the overnight trip had just started and presumably would still be going on.
When Jack and Katie are at the train station, Jack's head changes from looking ahead to looking at Katie instantly between shots.
The wedgie scene was really a wedgie. The director asked the two boys (Mike Erwin and Blaine Miller) what a bully would do to a geek. Blaine didn't say anything because he didn't want to get hurt while Erwin suggested wedgies. They did for or five wedgie takes in Miller's real underwear. This also lead to the ad-libbed line from Erwin to Logan Lerman's character "I'm gonna wedgie you so hard!".
When Jack is talking with Marcus before Missy walks in, the styrofoam food container that Jack is using changes position between shots.
When Randy and Grace are grading papers she refers to Bobby as being 12. However, after Jack finds out about them he calls Bobby a 13 year old.
The time of the bombing in Chicago is given as 8:03 am Central Standard Time. The date of the bombing is September 12th, which in present day is during Central Daylight Time in Chicago.
How can Bobby have so much trouble with his tie when you could see him do it flawlessly in episode 4 ("A Man of Faith", during the end)?
Jack is talking to Matt in the locker room. Matt admits to Jack that he's gay. Jack tells him he should talk to his parents. Jack then says, "It's 2003. . ." Considering they had the election episode last week, they should have corrected this episode so he would say 2004.
That scene with Matt is a flashback, thus taken place one year earlier than the present, which would be 2003.
When Courtney and Marcus arrive a little bit before the party, you can see a silver car pull up and park, then when it shows them at the door, the silver car pulls up again.
Bobby's face switches sides while kissing the bully.
*Most people are 16 year old sophomores. If you start K when you're 5, then you'll turn 16 during your tenth grade year. If your birthday is after Sept. 1, it's possible to turn 16 near the beginning of Sophomore year. If, for any reason, a child is held back from starting K at age 5 (not usually an indicator of intelligence, but of behavior or maturity), then that child would be 16 before starting Sophomore year.
The math on the chalkboard in Bobby's "challenge program" classroom is multivariable calculus, third semester college math. While some very advanced students take it as high school seniors, it is completely unrealistic to assume that eighth grade students would be doing it!
If Jack was intelligent enough to be accepted into the "Challenge Program", why is he a 16-year-old Sophomore, a year old for his grade?
In the official credits actor David Paymer was not credited as a guest star even though he does appear in the episode as the character Adam Chasen.