In this homage to the 1980s movie Tootsie, Stewie auditions for the American version of his favorite British kids' show Jolly Farm Revue, but when the talent coordinator tells Stewie that they want girls for the role, Stewie cross-dresses as a child actress to get the part. Meanwhile, Meg dates a normal guy (to the surprise of everyone in town), but Lois (who's feeling down about her age because of Peter's remarks) decides to steal him for herself.
This episode contains examples of:
- Betty and Veronica:
- Meg (Betty) and Lois (Veronica) over Anthony (Archie).
- Stewie (Betty) and Randall (Veronica) over Julie (Archie).
- Bait-and-Switch: Just before Stewie reveals himself to be a boy, Mother Maggie says "Today, children, we will learn about the letter 'T'". 'T' is the first letter in 'transvestite', which Stewie was about to reveal himself as shortly thereafter.
- Blackmail: Brian comes on to Stewie while he's dressed as Karina (while Stewie did encourage it, he didn't expect Brian to go as far as forcing Stewie to touch his penis, which is child molestation). Stewie uses this against Brian in order to get him to be Stewie's on-set guardian (as well as order Stewie some chicken fingers).Stewie: Brian, we both know I touched it. Now if you'd like to keep that just between us, I suggest you sit back down and order me some chicken fingers.
[Brian sits back down]
Stewie: See? We're having a nice time. - The Bus Came Back: Cleveland makes his first return to Quahog since he moved to Stoolbend. Driving five hundred miles in a short time just to see that Meg has a normal boyfriend.
- Butch Lesbian: "Bernie" and "Gert" are a stereotypical lesbian couple dressed as Bert & Ernie.
- Call-Back: Brian's attempts to goad Stewie into a discussion about Jolly Farm and the end where they go for ice cream are callbacks to "Road to Europe".
- Continuity Nod: Jolly Farm Revue, first seen in "Road to Europe", returns here. After Stewie gave up on the British version of the show in said episode, this episode has him watch the American version instead.
- Character Development: When Lois tried to seduce her boyfriend, Meg doesn't run off crying like she would earlier on in the show's run. She stands her ground, and reveals to Lois how wild their relationship really was.
- Dawson Casting: In-Universe. Jake Tucker is seen at the Jolly Farm auditions although they were looking for toddlers, Jake is 15 years old.
- Dirty Old Man:
- Herbert is seen in the crowd holding up an "I love Randall" sign. Nobody bats an eye at this.
- At the bar, Brian (who is considered old in human years) attempts to place Karina's hand on his crotch before revealing herself to be Stewie. While he didn't know Karina was Stewie, she's still clearly underaged.
- Downer Ending: Stewie doesn't get together with Julie due to her mother refusing to let him see her for disguising himself as a girl. Furthermore, she ends back up with Randall. To cheer Stewie up, Brian takes him to eat ice cream.
- Guy of the Week: Anthony, Meg's new boyfriend. To everyone's surprise he's normal.
- Implausible Deniability: Lois' excuse for Meg catching her making out with Anthony? That he raped her. She says this while she was on top of him.
- Incompatible Orientation: Karina (a lesbian and really Stewie in disguise) with Julie (who's straight).
- Love Triangle: Two of them:
- Meg, her boyfriend Anthony, and her mother Lois.
- Stewie, his co-star Julie, and her friend Randall.
- Mrs. Robinson: Lois becomes one by attempting to steal Meg's boyfriend.
- Never My Fault: Lois blames Peter for Meg hating her for making out with Anthony... because he insulted her age earlier. It’s also worth noting that it’s after she made out with Anthony that she mentions how Peter’s comments were affecting her.
- Noodle Incident: When Brian is looking over the photos Stewie has taken for his audition, he comes across one as slightly disturbing and Stewie freaks out.Brian: (agape at third photo) Oh my God!Stewie: (snatches photo; frightened) Please don't show Mom! He told me that's what a "head-shot" was!
- Shout-Out: The main plot of this episode is a parody of the film Tootsie and incorporates many references from that film, including the episode title, from a lyric in the film's title song by Stephen Bishop, "Go, Tootsie, Go!". Stewie's "argument" with his alter-ego is a parody of a similar scene originally having been performed in Tootsie.
- The Seinfeld theme is played after Meg catches Anthony cheating on her with her mother Lois.
- Parts of the American version of Jolly Farm Revue parody Sesame Street.
- The name of Stewie's female alter ego, "Karina Smirnoff," is the name of a professional dancer best known for her appearances on Dancing with the Stars.
- Stewie and Jolly Farm make a reference to Pan Am flight 103; A Boeing 747-100 carrying 243 passengers and 18 crew which exploded over Lockerbie, Scotland by a terrorist bomb on December 21, 1988; killing all 243 passengers and 16 crew members. The debris from the 747 fell on the town, killing 11 people on the ground, bringing the death toll to 270.
- The song at the end of the episode is "It Might Be You" by Stephen Bishop.
- Stacy's Mom: Anthony thinks Lois is still attractive even for her age, even calling her a "MILF"note when she reveals her attraction to him.
- "The Reason You Suck" Speech: Meg delivers one to Lois after she catches her attempting to steal her boyfriend.Lois: Meg, honey, I think we need to talk.Meg: I don't wanna talk to you!Lois: Look, I understand that you're upset.Meg: You made out with my boyfriend! How could you do that?Lois: I don't know, sweetheart. But I am so, so sorry. It was an awful thing I did. I never meant to steal him from you.Meg: Is that what you think? You stole him from me? Are you kidding? You couldn't steal him from me.Lois: Well, I do know a few things, Meg. And clearly, if I wanted him, I could have him.Meg: You really think you stand a chance? Look at you. You're old! You're nothing. You couldn't even imagine the things I do for him. And this isn't even about making out. This is about power tools. Yeah, I go to places you couldn't get back from. I'll do anything. You don't know me. (rips out her own tooth)Lois: Oh my God.Meg: He hangs me from the shower rods with your old bras, and then we laugh at you. Now, get out of my room!Lois: Well, when you're ready to talk...
- The Tooth Hurts: During her "The Reason You Suck" Speech to Lois, Meg rips out one of her own teeth at Lois just to prove a point to her.
- The Unfair Sex: When Peter is really feeling insecure about getting old and unattractive, he takes it out on Lois who retaliates by making out with a younger man.
- Unsettling Gender-Reveal: Stewie reveals himself to being in disguise as Karina when Brian attempts to seduce him.
- What Happened to the Mouse?: Lois never makes up with Meg by the end of the episode. Then again, this is Meg we're talking about.
- Worth It: Cleveland drives all the way from Stoolbend to Quahog to see if Peter's really telling the truth about Meg having a boyfriend. When he finds out it's true, he says that it was worth the 500 mile drive over.
