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Dexter is admiring Raven dreamily from afar, leaning on the side of his locker door from behind. Cupid walks by and tries catching his wavering attention to anything else but Raven.
C.A. Cupid: Uh, Dex? Dexter? [Waves.] Dexter Charming! [She waves her hand in front of his face.]
Dexter Charming: I'm up! [Slams locker door shut.] I mean, hi Cupid. [Nervous chuckle.]
C.A. Cupid: [Giggling.] What is up with you?
From Dexter's eyes, a dreamy aroma comes into view, encircling Raven who is giggling across the hallway with Maddie.
Raven Queen: [Giggling.] Maddie! [Flips hair.]
C.A. Cupid: [Letdown.] Oh...Raven.
Dexter Charming: You know, Briar is having that party on Friday, and I wanna ask Raven to be my date, but... I'm-I'm just afraid I'm gonna mess it up. [He scratches the back of his head.]
C.A. Cupid:  There are other girls at this school...
Dexter Charming: You'd ask Raven out for me?!
C.A. Cupid: [Holds finger out.] Not what I meant.
Dexter Charming: [Sigh.] I wish I was more like my brother. [He looks over to Daring's direction, who is flashing his smile at bystanding girls.] If I was the great Daring Charming, girls would just fall for me... [The girl students sigh and faint.] literally.
C.A. Cupid: Why don't you try your [Quotation marks.] 'asking out' skills on your friends? [She blinks twice and smiles, pointing to herself.]
Dexter Charming: That's a great idea! You're the best!
C.A. Cupid: [Closes eyes and inches closer to Dexter.] How about a little thank you ki―[Surprisingly, Dexter is off already.] huh?

Rumpelstiltskin: The art of conjuration: Making things appear from thin air...
Dexter attempts talking to Briar, who is nodding her head to the beat of the music she's listening to.
Dexter Charming: Hey, Briar, if I said something like, "You wanna go out with me?" - uh, would you?
Briar Beauty: [Snoring.]
Dexter Charming: Awww, man!

Dexter and Maddie are walking together in Book End.
Dexter Charming: So...did it hurt?
Madeline Hatter: Did what hurt?
Dexter Charming: When you fell from Heaven, 'cause, Maddie, you are an angel.
Madeline Hatter: [Excitedly.] You speak Riddlish too?! [She claps.] Aha!
Dexter Charming: Aww, man!

Dexter is out in the Enchanted Forest, practicing his skills yet again on a female troll.
Dexter Charming: So, this weekend - you, me?
Female Troll: [Dexter exclaims in surprise as she picks him up and gives him slobbery kisses.]
Dexter Charming: Ew...Oh, man!

Dexter is sitting on the balcony and Raven walks by.
Raven Queen: Mind if I sit?
Dexter Charming: R-Raven... um, you come up here too?
Raven Queen: Best place in the whole school to watch the sunset. Hey, would you go with me to Briar's party on Friday?
Dexter Charming: What?
Raven Queen: I'd rather just go with a friend. Less pressure that way, know what I mean?
Dexter Charming: [Nodding.]
Raven Queen: [Chuckling.] Hexcellent. I'll see you Friday. [Walks off.]
Dexter Charming: [Jumps to his feet.] YES! [Sing-songy.] I'm going to a party with Raven Quee― [Falls off the edge of the balcony.] nnn! [Grunts as he bounces off a bush.]
Cupid finds Dexter and is on the side reading a book.
C.A. Cupid: Dex!
Dexter Charming: It totally worked! [He kisses Cupid on the cheek.] You're the best!
C.A. Cupid: [She cups her cheek and giggles in response.]