On advice from Dr. Homer, Tommy's dentist (Didi prefers calling him a "tooth fairy"), Stu and Didi want Tommy to start drinking from a cup. Tommy, however, wants to stick with the baby bottle.
- - Description from Klasky Csupo.
Didi and Stu are taking Tommy to his first ever dentist appointment now that he's begun teething. Didi consults Lipschitz and insists they refer to the dentist as the tooth fairy so Tommy won't be afraid. Stu himself is still uncomfortable about dentists and worries about what he'll say about Tommy's tooth.
At the dentist's, Tommy has become nervous and refuses to open his mouth! After some coaxing and bribery, Tommy opens his mouth and the dentist examines his sole tooth. It checks out just fine, and the Pickles begin to leave. A bottle falls from Tommy's diaper bag, however, and the dentist quickly stops them. He claims that bottles rot and ruin teeth and Tommy needs to be weaned at once. Worried (and horrified) by the idea of cavities and braces, Didi and Stu agree to wean Tommy tomorrow. Use Mr. Tippy cup of milk like a big boy.
After breakfast Didi washes all of Tommy's bottles in preparation of packing them away. Tommy, unhappy, looks around the house for any bottles Didi might have forgotten. However, Didi was very thorough and after looking in all of his hiding places, can only find a single, very dusty, bottle. Tommy has a difficult time reaching it and has to knock it out into the open. Unfortunately, it rolls straight towards Didi, who picks it up and washes it before Tommy can get to it.
Later in the day, Betty and the DeVille twins have come to visit. Betty is very surprised to hear Tommy is being weaned already and says she was told not to even consider weaning the twins until after they turn two. Didi is surprised by this advice and appears to rethink weaning Tommy when Betty says the dentist was probably a quack.
Meanwhile, in the playpen, Tommy shares his predicament with the twins and is very jealous of the bottles they're currently enjoying. The twins agree his mom is being harsh, but refuse to share their bottles with him. Tommy begs and bribes the twins, but they still refuse to share their bottles. Finally, Tommy uses the old "Look, what's that?!" trick to try and grab one of their bottles. He nearly succeeds, but Didi catches him and removes him from the playpen so he can't take their bottles.
The day moves on and Tommy takes his afternoon nap. Tommy dreams first that there are bottles everywhere, but his mom takes them away because he's too big for bottles before he can have any. Then he's in the kitchen, but big; he can practically touch the ceiling and he accidentally crushes his high chair when he tries to sit.
Down at his feet, a voice gets his attention; it's one of his old bottles, but very, very tiny! Tommy picks up the bottle, but the bottle says Tommy is too big for him and bounces away. Tommy chases after the bottle and quickly comes across a giant version of Mr. Tippy! Mr. Tippy demands Tommy to drink from him and chases after Tommy when he tries to flee.
Tommy becomes trapped against the edge of a cliff, but a giant bottle appears and saves Tommy from Mr. Tippy. Tommy is confused because his parents said he was too big for bottles, but the giant bottle says he's a grown-up's bottle so it's okay. Tommy wakes up seconds later. Didi asks if Tommy had a nice nap; Tommy simply stares at her.
Downstairs in his high chair, Tommy is again offered Mr. Tippy. A clearly miserable Tommy simply swats Mr. Tippy down to the floor, refuses to have anything to do with Mr. Tippy. Grandpa Lou says he thinks weaning Tommy this young is ridiculous and claims his brother used a bottle for fifteen years and it didn't wreck his teeth. Stu offers Tommy him some cups of milk, but Tommy just swats them onto the floor, and some of the glass cups broke, and Spike licks some milk on the floor that spilled. Stu and Didi took Tommy into his room, and put him back into his crib. Didi tells Tommy that they can't give him the bottle, and promise him that he'll get used to the cup. Tommy begins to cry, then Stu and Didi leave his room, turned off the lights and closed the door. Both feel terrible, but agree to stand firm and that Tommy will eventually have to get used to drinking from cups.
Later that night, Grandpa Lou sneaks into Tommy's room to secretly give him a bottle, but is caught by Stu. Stu, however, also has a bottle he wants to secretly give Tommy. Didi comes in moments later with the intention to give Tommy a bottle, too. The grownups realize they're all just as unhappy about weaning as Tommy, and decide to switch back to bottles in the morning. The three of them head back for bed, and Grandpa Lou notices he no longer has the bottle. He looks back at the crib briefly before leaving too. After he leaves, Tommy sits up and eagerly drinks from the bottle he secretly snatched from his grandpa.
- Even though Tommy is not weaned by the end of this episode, in Rebel Without a Teddy Bear, Tommy is shown to be able to drink from a cup.
- A Tina Trousers doll is shown in the dentist's office (used as a lure to get Tommy to open his mouth) after its first appearance, two episodes prior.
- Stu is revealed to be afraid of dentists in this episode.
- Although Angelica is mentioned, and is revealed to go to day care every day, she doesn't appear in this episode.
- This appears to be a continuity error, as Angelica nor her parents never mention Day Care in other episodes, and is constantly left in the care of her Stu and Didi. She also is seen to not get along with other children, as in "Educating Angelica", which begs the question as to why Angelica has not been pulled from the daycare. However, since this is an early episode, it could easily be inferred her character has not been fully estabilished
- When Dr. Homer is checking Tommy's mouth he isn't wearing gloves. Also, when he checks Stu's teeth he still doesn't have gloves on.
- Dr. Homer is a reference to Homer Simpson on the Simpsons.
- Chuckie is seen drinking from an orange Mr. Tippy seven seasons later in Finsterella.
- The possibility of Tommy needing braces is mentioned. Ironically, it's Chuckie who needs braces later in life.
- Like in "Slumber Party", the clock on the wall in Tommy's room has no hands.
- Dr. Homer's Reptar mask is shown with white eye sclerae instead of the usual orange sclerae. This also happens in this episode's companion episode, "Incident in Aisle Seven".
- When Didi is on the phone with Betty the hand that is on her waist is backwards.