Along with sweet and innocent romance, comedy is one of the major elements of the Tokimeki Memorial series' success. Here are a few of those funny moments, listed by flagship games of the franchise.
Tokimeki Memorial 1
The "Mid-day NijiBen" Event in the Drama CD version of Nijiiro no Seishun: Yoshio, somewhat jealous of the main protagonist who got a bentô from Saki, and annoyed by his obliviousness, funnily tries to steal the bentô from him, leading to bickering between them:
Yoshio: But you don't get it at all! I can't let such a guy like you eat it! It is I, the Great Yoshio, who will stuff-it-doooown!!
Protagonist: The bento Nijino-san gave me! Let it go!
Yoshio: Don't wanna!
Protagonist: Let - it - GO, I said!! Are you a kid or something~?!
Yoshio: Gimme some to me too~, come on~
Yuina's monologue track in the Drama CD "Tokimeki Memorial: Nijiro no Seishun Forever, Volume 2", which explains the Nijiiro no Seishun event where the protagonist gets hit by a soccer ball each time he succeeds at picking up all balls scattered on the field: she's in the process of completing the ultimate weapon of her "World-Conqueror Robo", the Soccer Ball-firing "Hyper Mega Bazooka", and in order to test it, she programmed the weapon's sensor to lock on the protagonist each time he says a specific key word, which he happens to say when he finishes picking the balls.
Yuina: I'm counting on your cooperation from now on for data-gathering, N°16-kun. Fu fu fu...
Yuko and Yukari's Manzai scene in Irodori no Love Song. Given that Yukari, the boke of the two, is by nature a Cloud Cuckoo Lander, we're never really sure if they're playing their role, or if they're arguing for real, with Yuko improvising depending on Yukari's nonsensical answers. One thing is sure though, the in-game audience finds them really funny too.
The "Great Yoshio Kick", in battle phases of Tokimeki Memorial 1. Yoshio not only hilariously fails at damaging the enemy, he One-Hit KO's himself with it!
Junichiro, when he finds a love interest. The scenes where he shyly talks about it, complete with Luminescent Blush, are utterly adorable and funny to see at the same time, and it's even better when Takumi teases him about it.
Junichiro again, this time at the 3rd Year's School Festival, if you choose to do a School Play. He plays as the prince, and when the actress playing as the princess gets suddenly ill, Takumi takes her place on the fly. Cue this golden line from Jun after the play is over:
Mei trying to make dinner for the protagonist during the 3rd Year's Club Training Camp, after witnessing her butler Sakunoshin making it and her beloved protagonist liking it. But she can't escape the Tokimeki MemorialunderclassmenLethal Chef curse, to the protagonist's dismay...
Kotoko discovering, to her horror, that tonight's dinner at the club's Training Camp is curry. Her reaction and face at that moment are absolutely priceless.
Kotoko again, when going on a date at the Ski Resort. She turns into an angry snowman after falling, swearing never to come back.
Miyuki's Take That, Audience! moment in Dancing Summer Vacation. See the trope's entry for more details on that one.
Tsugumi's jealousy event, when you go to the café she's working at, along with the girl you are in a date with. You know you're in for a big moment when you know she's the game's resident Tsundere.
Fumiko's confession; which whether an acceptance or a rejection, involves broadcasting it (accidentally) over the school broadcast system. If it's successful, it's because she was too shy to make it in person, and lured the protagonist to an empty classroom, with the intention of broadcasting it only in that room. If not, it's because the protagonist went to the broadcasting room to confess, and was rejected while the mic was still running.