Farewell to You Baby by Carl Martin is played as Homer breaks up various couples.
Word Up by Cameo is played during Lisa's cross-word competition.
Cherish by The Association is played after Homer wins Lisa back at the end of the episode.
The "words that have been removed" sequence references the sequence in award shows in which deceased entertainers have died between last year's awards show and this year's.
The scene where Lisa helps the license clerk with a crossword is a reference to the pilot episode of The Big Bang Theory, where Leonard helps the high IQ sperm spark bank receptionist with a crossword.
As spoken, Homer's message to Lisa was, "Dear Lisa, you make me so happy. Really, really, really happy. Sorry, he told me I needed a hundred-and-forty-four letters. What was my point again? Oh, right. Bouvier or Simpson, I cherish you." For the record, this little speech has 147 letters, not 144.
Ironically, if Homer had said "I needed a hundred-forty-four letters." Taking away the "And." He would have exactly 144 letters.
Mathmatically, the "and" shouldn't be in there anyway, as saying it in numbers actually means 100.44.
The words in Lisa's Hopscotch Crossword are: justice, happier, vegan, rebel, practicing, over, think, PTA, cerebral, rights, saxophone, playtime, lemonade, paradox, Jimbo, recess, Ralph, overachiever, recital, Krabappel, uniter, PhysEd, phenomena, and tree.
Words that have been removed from the dictionary in the past year: SKEDADDLE, NIXONIAN, ZOUNDS, MIMEOGRAPH, HOOTENANNY.
Just after Bart says "Speaking of San Francisco people mover--" the show cuts to Homer at gay club helping Grady break up. During this transition the following can be seen on the screen for a split second: Scene 151, Take 2, Akom and Film Roman Fix.
Tim Long credited the 2006 documentary Wordplay, which chronicles the national crossword puzzle championships, as the main inspiration for this episode.
In order to win Gil tricked Lisa by telling her a sob story then dropping his fake glasses so he could complete the crossword while Lisa picked them up, however what Gil did was cheating, therefore he would have been disqualified and Lisa would win by default.
When Word Up by Cameo was playing whilst Lisa was winning the crosswords, she jumped on a trampoline to put the dot on the i, however, crosswords are done with capital letters so there would be no reason to put the dot.