Spring is in the air at Ever After High, and following their true heart's desires is the only thing on students' minds. Or it was, until C.A. Cupid came across The History of True Hearts Day book and rallied the students to spellebrate the long-lost True Hearts Day holiday.
It is spring in the world of Ever After and love blossoms along, undaunted by the reality that the population's romantic potential has already been laid out within their destinies for them. Even C.A. Cupid, daughter of Eros, is bound by the rules of Ever After. But being from another world, these rules do nothing to stop her from pining after Dexter Charming. He does not feel the same, but appreciates her friendship. It is because of this that he entrusts her with a book he found in the forbidden section of the library called The History of True Hearts Day. Cupid is overjoyed and immediately heads to Headmaster Grimm's office to convince him to return the holiday to its glory of years ago. Headmaster Grimm, however, refuses to do so, calling the holiday dangerous because it doesn't fit with the pro-destiny philosophies of the school. Though he fails to take the book from Cupid, he forbids her to talk about it with anyone. Intimidated but not easily shaken from her goal, Cupid meets up with Briar and tells her all about True Hearts Day through charades. She easily convinces the resident party girl to help her organize a secret True Hearts Day dance.
Down in the Enchanted Forest, Duchess enlists Sparrow to help her obtain evidence of Ashlynn's and Hunter's secret romance. They find Ashylnn and Hunter on a romantic date and Duchess, after taking pictures, threatens to expose their secret and take Ashlynn's place in the royal rankings as well as her Happily Ever After. The threat ruins Ashlynn's and Hunter's date, prompting Ashlynn to return to The Glass Slipper to think the situation over. Apple pays the store a visit and notices Ashlynn's distress, but Ashlynn declines to share her problem with Apple, who is widely known for her pro-destiny mindset.
Back at Ever After High, Cupid holds her radio show to help others with their love problems. Dexter calls in to gain advice on how to confess his love to Raven Queen. Despite precautions, Cupid recognizes the caller as Dexter. Heartbroken but dutiful, she tells him to put his feelings down on parchment. Thanking Cupid, Dexter quickly goes to write Raven a love poem. Once finished, he leaves the poem at Raven's locker for her to find. He hides nearby and watches as his crush finds the gift, but things go differently than he anticipated. Because he signed the poem as "D. Charming", Raven incorrectly interprets it to be from Daring Charming, leaving Dexter's heart worse off than before.
- The webisode takes place in spring, which differs from the Getting Fairest doll log canon, as that has True Hearts Day take place in February.
- Cupid's MirrorCast is shown. In Monster High, the franchise, and in the school of Monster High, she has a popular radio show called On the Air with C.A. Cupid.
- Apple's earrings are red when she is courted by three boys, but golden in all other scenes.
- The step-librarian in the red dress is drawn without her glasses when she slams her hand onto her desk.
- The step-librarians' rings change hands or disappear throughout the webisode.
- Cupid sports two bracelets when she grabs the book off the headmaster's desk.
- During Cupid's close-up when she discuss about celebrating True Hearts Day with Briar, her left wing is missing.
- When Hunter pulls back the bow, his bracelet is on the opposite wrist.
- When walking up the stairs with Kitty, Lizzie's outer skirt is missing.
- This is the first of three longer webisodes that make up "True Hearts Day".