Seth MacFarlane guest stars as Ben, the latest man come to sweep Marge off her feet after Marge mistakes an adulterers' dating website for a cupcake delivery website and the two bond over a Downton Abbey-esque TV show, while rude comedienne Lisa "The Queen of Mean" Lampanelli guest stars as Ben's angry wife, Ramona. Meanwhile, Homer, Reverend Lovejoy, Moe, Lenny, Carl, and Larry the Lush team up to renovate a steam train that was once a part of Springfield's most glamorous outside mall as part of Marge's wedding anniversary present.
Tropes:
- Actor Allusion: Ben's line By the way, this is my real voice could be one, as he's voiced by Seth MacFarlane, well known for voicing many different characters. Ben's voice is very close to Seth's real one.
- Brick Joke: When Selma sees how many matches Marge got on Sassy Madison, she considers getting married (yet again) just so she can join the site herself. The musical epilogue shows that Ben gave the site another try after failing with Marge only to wind up meeting Selma, who used fake photos in her profile.
- Comic-Book Time: Homer and Marge celebrate their 10th anniversary, which is less than half the time the show has been on the air.
- Continuity Nod: The flashback at the beginning shows baby Bart preferring Ned to Homer, as his 10-year-old self did in The Movie.
- Exact Words: In her dating profile, Selma describes herself as "smoking," which she is, as usual.
- Forgotten Anniversary: For the majority of the episode, Marge believes Homer forgot their anniversary. Subverted in that for once, not only did Homer remember their anniversary, but was actually putting a lot of effort into it.
- Grand Romantic Gesture: In a rare occurrence, Homer put in a lot of effort into doing this for Marge. Even better, it went as planned.
- Happy Flashback: When reflecting on their first anniversary Homer recalls him, Marge and infant Bart going to a mall and riding a kiddie train, and it being a near perfect family activity. This is what leads to Homer going to the same mall only to see everything being torn down.
- Imagine Spot: Marge tries hard not to fall for Ben when he is not around, making her mind picture him doing romantic gestures for her.
- Is It Something You Eat?: Marge says she has been feeling melancholy, this leads Homer to say, "Mmmm... melon-collie..." and imagine a dog made out of melons.
- Lampshaded the Obscure Reference: When Lisa references George Orwell while tattling on Bart:Marge: Can I have one hour of grown-up time where you two aren't tattling on each other or using obscure references?
Lisa: Orwell, obscure? The author of Animal Farm?
Bart: Grandpa says he was a commie. - Leaning on the Fourth Wall: When people wonder if Homer and Marge can last to their 25th Anniversary, Bart says that nothing should last that long. This was the last episode of the 24th season.
- One Dialogue, Two Conversations: Marge overhears Homer talking with Moe about how the strippers have arrived, Moe was actually talking about the paint strippers who were cleaning up the train. "Whoa buddy, that's coming right off!"
- Poor Communication Kills: Pretty much all the problems in the episode stem from Homer's efforts to hide his anniversary surprise making him look really, really bad.
- Series Continuity Error: In a flashback to Homer and Marge's first wedding anniversary, they already know Ned Flanders and let him keep an eye on baby Bart when they run into him at the mall. In "Lisa's First Word," they met Ned upon moving into Evergreen Terrace while Marge was heavily pregnant with Lisa. Even allowing for a possible Retcon as of "Dangerous Curves" (which shows Homer and Marge's real first meeting with Ned occurring when the former two were teenagers) doesn't explain why baby Bart already knows Ned very well to the point of considering him a Parental Substitute for Homer.
- Show Within a Show: Upton Rectory, the Downtown Abbey-esque TV show Marge and Ben bond over.
- Stepford Smiler: Marge tells herself to hide her disappointment with Homer the same way she always does: suck it in and smile.Chief Wiggum: There goes a woman who's unhappy with her partner.
Lou: Yeah, I know how she feels.
Chief Wiggum: Yeah... What was that?
Lou: [Stepford smiles]
