Airdate: Monday, August 18, 2003
Sender: Dynomite, Boston MA
"Dy-no-mite!" from Boston in "the state Boston's in" wants to know what Strong Bad thinks happens when Homestar and Marzipan go out on a date.
Strong Bad's whipped up the Homestar Runner and Marzipan Extra Real Dating Sim XR in order to simulate "the lurking horrors" of a date between the two (which seems to involve going "Duh!", "Buh!", "Fuh!", and randomly praising Strong Bad).
Live from Marshmallow's Last Stand, Homestar is trying (and failing) to entertain Marzipan by playing a game where she has to guess if he's going to say "Sid Hoffman" or "Sid Frenchman" (and not playing very fair, since Homestar ends up saying "Sid Hoffrenchman").
Strong Bad has other cameras set up as well, including one hidden in a ring Strong Mad is wearing so Strong Bad can see his big bro punch people in the face (such as Strong Sad), and another hidden in Strong Badia. On Camera 3, Strong Bad observes The Cheat falling for the "security counter-measures" he's set up, including a shocking trap on the Tire and a cardboard cut-out of a bear holding a shark set up behind the fence, which scares The Cheat clean away.
Back at Marshmallow's Last Stand, Homestar idly kicks Marzipan in the shins, and then spits out his coffee all over her when he finds Strong Bad has replaced it with "Super Mud".
- Bears Are Bad News: This email introduces the Bear Holding a Shark, which handily combines this trope with Threatening Shark.
- Easter Egg: Both Homestar Runner's "Sid" Game and the Homestar Runner and Marzipan Extra Real Dating Sim XR are playable.
- Incredibly Obvious Bug: Strong Sad can apparently tell Strong Mad's ring has a camera hidden in it, even while in the middle of being pummeled senseless.
- Harmless Electrocution: The Cheat is briefly stunned by a shock-trap Strong Bad installed on the Tire.
- Her Code Name Was "Mary Sue": The Extra-Real Dating Sim has an option to make Homestar and Marzipan randomly praise Strong Bad.Homestar: Strong Bad's muscles can beat me up!
Marzipan: Strong Bad is on point!
- Punctuated Pounding: Inverted. Strong Sad is the one shouting as he's pummeled. "Ow! Please! Quit! Punching! Me-in-the-face!"
- Shoe Phone: Strong Mad has a ring with a camera hidden in it (though not very well, if Strong Sad's able to spot it).Strong Sad: Since when did you start wearing a class ring? With a camera in it?
- Strong Bad's delivery of "Dy-no-mite!" is a reference to Good Times.
- Strong Bad's "We also switched Homestar Runner's gourmet coffee with Super Mud!" line refers to a famous series of commercials for Folger's Crystals instant coffee.
- Spit Take: Homestar spits out his "coffee" after Strong Bad replaces it with "Super Mud".
- Surveillance as the Plot Demands: Strong Bad had The Cheat set up hidden cameras around Free Country USA.