Matt goes on a date. Everything seems to be going well until the date asks him, "your place or mine". Matt immediately remembers an incident when Tom's feet were eaten by irradiated socks and visibly freaks out. Before Matt says anything, his date has already left.
- Matt - Matt Hargreaves
- Tom - Tom Ridgewell
- Katey "RED" Harding - Jenny Bingham
- Balloon Head Fred (cameo)
- Mrs. Head (cameo)
- Pearl "iamprikle" (cameo)
- Johnny "Skifle" (cameo)
- This is the first Eddsworld animation entirely animated by Paul ter Voorde.
- This episode marks a rare occasion in the Eddsworld series where Edd is neither seen nor heard. Tom does not appear in this episode, but his voice can be heard in Matt's flashback.
- At the start of the episode, Balloon Head Fred, his wife and their balloon giraffe son can be seen sitting at a table, along with Johnny, a character from Bumming Crew (made up of some of Paul's friends). Seen admiring him is Pearl of Bumming Crew fame as well.
- When Matt is having his flashbacks, his room is hinted to be incredibly messy. This was visually shown in Hammer & Fail, so chances are that Date Night might've taken place before Hammer & Fail, or perhaps a mishap might've taken place after Hammer & Fail when which Matt's room might've spontaneously become messy again.