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.
Tokimeki Memorial: Girl's Side 1
Shiki Mihara's response to the flirtatious blond date disturber is priceless. Rather than get aggressive, he patiently tells him to look at himself and compare himself to the two of them, making it clear that he thinks the heroine is way out of the guy's league, and nonchalantly dismissing him with a palpable air of "Begone, peon!" The poor dope doesn't even know what hit him.
On the subject of Shiki, it's impossible to watch the SD animation of him and the heroine riding the merry-go-round at the amusement park without laughing. Most of the guys are distinctly unimpressed by the merry-go-round, but Shiki? Shiki loves it. And he's not shy about showing it.
Then there's the CG event in which Shiki shows the heroine the stone bust he sculpted of his mother. He drapes himself suggestively against it, waxing dramatic about how he wishes she could be there with him, and the heroine draws the conclusion that she's dead... but no, she's fine, and probably at home cooking a whole pig for dinner.
Himuro's third-year Christmas event, in which the heroine badgers him to take her with him to his friend's bar. He adamantly refuses, insisting that it's no place for him to take a student.
His bartender friend then effectively blackmails Himuro into playing the piano while he's there, over Himuro's griping.
Goro Hanatsubaki's funniest moment is unquestionably the CG scene in which he comes looking for Principal Amanohashi, brandishing a tiny gold-sequined swimsuit that he wants Amanohashi to try on. Amanohashi hides from him in terror, gesturing frantically to the heroine not to let on that he's there.
In Hibiya's ending, he messes up his confession, asks for a redo, leaves the chapel, walks back in and starts from the beginning.
Tokimeki Memorial: Girl's Side 2
"Ninomiya Kinjiro featuringu Chrisu!" Christopher Weatherfield decides to spruce up a statue on the school grounds by painting it garish red and blue to make it look more 'fashionable,' and cheerfully relates to the heroine how upset the teachers got over it. "I was chased with a mop!" His cheerful obliviousness to the reasons for their objection is what really sells it.
The funniest date interruption in GS2 is probably when the salesman approaches the heroine while she's waiting for Teru. When Teru arrives, he promptly gets on the heroine's case for enjoying the attention, and the two of them bicker over whether or not Teru is jealous; the salesman awkwardly suggests they shouldn't be fighting if they're on a date, prompting both of them to tell him to butt out.
Harry in the school play in the third-year culture festival, playing Captain Von Trapp opposite the heroine's Maria. It's usual for the guys to ad-lib a little during the play in their respective routes, but Harry throws the script completely out the window, abandoning character altogether to have his epiphany while the heroine struggles to keep the scene on track.
"Maria": Captain, you just got your name and that whole speech completely wrong!
Itaru Hikami's escalating efforts to get Wakaouji to stay put and answer his chemistry questions. After twice losing out to snack foods, he resorts to fighting dirty:
Itaru: You recognize this, right? It's the much-talked-about "Extreme Melon Bun".
Wakaouji: No way. The store only got them in yesterday.
Itaru: Of course, I abused my power as a student council executive to get this.
Wakaouji: Hey, Hikami-kun, isn't that unfair?
Itaru: I know. So if you do not want me to walk down this road any more - if you want this "Extreme Melon Bun"... Will you answer my questions?