Actor Allusion: In Tokimeki Memorial 3, both Yukiko and Chitose are best friends and in real life the seiyuu that play them, Akemi Kanda and Sayoko Kawaguchi, are also best friends.
Cash Cow Franchise: Oh boy. This series has so much merchandise, it even has several official books referencing the existing merchandise!!
Executive Meddling: Back then, Konami organized a character poll on the famous magazine Famitsu, in which the readers would decide which character will become the heroine of the second Drama Series game, the would-be Irodori no Love Song. Despite the poll results giving a large victory to Miharu Tatebayashi, for various reasons the producers decided to go with the poll runner-up, Ayako Katagiri. They still later recognized Miharu's popularity by making her the co-heroine of the 3rd Drama Series game, Tabidachi no Uta.
Fan Translation: The SNES version of the first game is sadly notable for having lots of attempts at creating a translation patch; all of them invariably went to stall for a reason or another.
Follow the Leader: It's the game series which defined the non-hentai Dating Sim genre, after all.
Name's the Same: Kasumi Asou must not be confused with the Phantom Thief of the same name of City Hunter. When their names are written in Japanese, the only difference is their first name, City Hunter Kasumi's being written in Hiragana, while Tokimemo 2 Kasumi's is written with Kanji.
No Export for You: This game series is one of the most famous victims of this, for obvious reasons.
One-Hit Wonder: Yumi Saotome is the only role her seiyuu Yoshiki Kurin ever voiced.
Remade for the Export: In 2007, Konami tested the waters in America by creating Brooktown High, an American High School version à la Sims of Tokimeki Memorial. But what they failed to notice, is that what made the success of Tokimeki Memorial is its beautiful anime graphics, and its humor and light-hearted atmosphere; no wonder a game with fugly 3D designs, insipid characters and crappy dialogue like Brooktown High, already not helped by its concept and by virtually non-existent publicity, bombed royally.
Talking To Herself: Hikari Tachibana voices both Shirayuki twins, and as such this occurs in a few scenes where both are present (most notably the Girl with Psycho Weapon scene described above, as well as the scene where they finally reveal their switcheroo game to the protagonist).
What Could Have Been: According to the Japanese version of The Other Wiki, Yukari Koshiki is a shining example of this trope. Indeed, Yukari’s initial name was Shouko Hoshino (星野翔子), but because the PC-Engine’s Kanji system couldn’t display the kanji 翔 (shou), her name was changed to the current “Yukari Koshiki”. Even more memorable is that, in the game’s development’s initial stage, she was planned to be the game’s second heroine at Shiori’s side (and be hostile towards her), but the idea was ultimately scrapped. Her personnality was also radically different: she was planned as a Delinquent instead of the Cloud Cuckoo Lander she is in the final version. Finally, there was a planned game sequence in which, when you phone her to set a date, sometimes the call would be redirected to her Overprotective Dad’s cellphone: a brilliant ideathat was also scrapped in the end. Several of those ideas would be used 15 years later in Tokimeki Memorial 4, to create Yukari's Expy, Kai Ryukochi.