Yuuken Yuu Enma is an average Japanese high school student preparing for an upcoming kendo tournament. On the night before the competition, however, a black carriage crashes into him. When he regains consciousness, Yuu finds himself at Night Raven College—a premier academic institution in the magical world of Twisted Wonderland. Only a chosen few with exceptional magical talent are admitted into the school, so it is a mystery how a human with no magic ability ended up here. Although Yuu desires to return home, it is easier said than done. While the school's headmaster searches for a way to send him back, Yuu is assigned manual labor around the campus. But due to the chaos at the school's entrance ceremony following his arrival, Yuu has a target painted on his back as far as Heartslabyul dorm leader Riddle Rosehearts is concerned. Yuu meets and befriends Heartslabyul freshmen Ace Trappola and Deuce Spade; yet soon after, Ace and Deuce land in a situation that results in their expulsion. As the pair seek to redeem themselves, Yuu accompanies them on their perilous mission to fix school property. However, forgiveness does not come easily from the Crimson Tyrant in charge of Heartslabyul, who may have an ulterior motive behind his strictness.

Ayu Tateishi is a popular second-year student at her middle school admired for being calm, cool, and collected. But this carefully preserved image was all crafted to catch the eye of her crush Tetsushi Kaji, who once complimented her for those qualities. Studying, playing tennis, and finding chances to speak with Tetsushi are all that are on Ayu's mind—until the day she finds a mini-computer underneath a bench. After returning the item to Nina Sakura, a girl who was searching for a lost item earlier, Ayu is chosen by Nina as a confidante for her secret. When the school's two tennis teams have a dispute regarding use of the courts, Ayu is forced to settle the matter by playing against Hiroki Tsujiai, the captain of the boys' team and Tetsushi's best friend. While dreading the prospect of losing and embarrassing herself, Ayu is approached by Nina, who is revealed to be a witch who came to Earth after failing to graduate from the Magic Kingdom's middle school. Wanting to help Ayu win the match, Nina imbues a piece of chocolate with a spell that just might come in handy...

It's the first day of the new school year. 5th grader Ari and her best friends Suha and Min have started an after school activity called the Problem Solving Club. However, no one seems to have any problems that need to be solved. Disappointed Ari ends up discovering an unconscious hamster on the road. Amazingly...the hamster begins to speak. I must find the magic ring... (Source: Official Youtube Channel of Flowering Heart)

The final DVD volume contains two specials: Tokimeki no Yuuki Episode 18 (sometimes labeled 17.5), which was never broadcast on TV. It features the swim captain, Utsumi Koayu. Tokimeki no Sentaku Episode 25.5, a recap of all episodes but the last, which was initially displayed at the Konami booth for the Tokyo International Anime Fair in 2007.