Ricky is feeling depressed because he has no Valentine, so Baby Lamb, Cow, and the others help set him up on an impromptu date. Only, his so-called "date" is not really real, per se. Ricky's gonna find out eventually.
Ricky is slowly walking by the couples, feeling depressed. He goes to the bathroom and talks to himself in the mirror, saying he's wasting Valentine's Day pretending to be cupid. He shames himself for wanting a girlfriend to come to him when he should've done the opposite. He doubts he'll get a date by the time Valentine's Day's over. The others overhear Ricky's self-conversation in the bathroom and feel bad for him and Baby Lamb says they know what they must do.
Meanwhile, Mickey and Minnie talk about what they plan to do for a date and are about to kiss until Baby Lamb and Cow interrupt them. They apologize for disrupting them and seeks advice from advice on dating because they're planning on having Ricky do a blind date but neither of them know anything about dates and asks if Mickey and Minnie can help them since they're experts when it comes to love.
Donny puts a bowtie on Ricky, who's surprised he's gonna go on a date. He wonders who will be The Shipping Fairy, but Donny tells him he won't need to worry about that since he took care of everything, and that all he needs to do is relax and let the night go as smoothly as possible. Donny then takes off Ricky's cupid wings. Cow is then disguised as a female dog, who will be Ricky's date, so he can be happy on Valentine's Day. Cow asks if Ricky will love the disguise too much and he will spend the rest of his life wearing a paper cutout. Baby Lamb says this is only for the night and he will do the talking. As long as they stay hidden, Ricky will buy.
Donny says he sees Ricky's date, named Riley, and Ricky immediately falls in love with "her". Donny says it's going off to a great start, but Alphabet Pal doesn't think it's going to end well. Ricky then proceeds to smooth-talk his date, using pick-up lines, annoying Belle and Alphabet Pal. Donny says chicks dig it and then decides to serenade the two by singing. Ricky tells Donny to butt out so he can have an intimitate date with Riley. Afterwards, Ricky continues to smooth-talk Riley, still impressing her. Donny is amazed she's digging Ricky. Ricky then tells her the secret that he pretends to be The Shipping Fairy so he won't be sad on Valentine's Day but now he doesn't have to worry because he's proud to call her his Valentine, and Riley says the same to him.
Donny then takes one of Cupid's arrows, and sticks it on Riley, oblivious that it's actually Cow in disguise. Cow then flies out of the disguise and begins to fall in love with Ricky, who's shocked about Riley. Baby Lamb's disappointed that their cover was blown. Ricky's angry at the two and then wonders why there's an arrow on Cow's butt. He then takes the arrow off Cow.
- Ricky Bowers
- Baby Lamb
- Riley (disguised)
- Alphabet Pal
- Donny Dolphin
- Mickey Mouse
- Minnie Mouse
- The Count Von Count
- Winnie the Pooh
- Homer Simpson
- Marge Simpson
- Chief Mark
- Officer Patricia
- Red Bird
- Kiss the Girl
- This is the first time Mickey and Minnie Mouse have spoken in the series, only it's through archival audio of the late Wayne Allwine and Russi Taylor voicing them from "House of Mouse" on account of Simon A. doesn't do great impressions of either character.
- When Ricky first fell in love with Riley, a Simpsons clip of Bart Simpson catcalling is shown. This is one of the first times in the series a gag featuring a clip relating to the scene is shown.
- INNUENDO: When Ricky asks Cow why there's an arrow in his butt, Cow says he doesn't know but says "You wanna know what I really want in my butt?", implying something sexual.