"Date Night" is the first segment of the fifty-fifth episode of Big City Greens.
Gabriella calls the Greens residence to ask Cricket out on a date. As Cricket answers, both Gramma Alice and Bill are surprised to hear that he has a girlfriend. Gabriella wants to go see the new America Rat film which Cricket happily agrees to; the only catch is is that they need to have a chaperone and Gabriella's parents are unable to go. Cricket immediately asks Bill to chaperone for them and he agrees. However, Bill is so engrossed in the idea that Cricket has a date that he decides to take it upon himself to try and make it "perfect". When Bill prepares himself by dressing up nicely, Cricket openly admits that he regrets asking him to chaperone.
They pick up Gabriella and as she and Cricket attempt to talk, Bill starts playing romantic music in the truck very loudly. Despite Cricket's attempts to turn it down, Bill continues to blare it. They pass by the movie theater with Bill arguing that they should eat first. His choice of dining however, is the three60 restaurant which Cricket and Gabriella immediately detest. Bill forces them in and has the whole place suited to his liking as opposed to the kids. Cricket apologizes for how the night has turned out as the place is filled with the type of people he dislikes. While Gabriella agrees that Bill is acting weird, she believes that this is their chance to take advantage of the situation and prank the elite that dine there.
Cricket and Gabriella have fun pranking, but as they are about to increase the speed of the rotating restaurant, Bill stops them and forces them to have a dinner date the way he wants them to. Cricket and Gabriella become miserable and are unable to do anything. Upon seeing his expression, Bill realizes that he made a terrible mistake and saves them, by increasing the spinning speed. Bill apologizes to the two just as the speed stops. Cricket and Bill hug it out while Gabriella claims that Bill is the best chaperone she has had and that she would love for him to do it again on the condition that their outings be this fun and Cricket adding he'd just drop them off and pick them up. As they are about to go to the movies, the manager comes out and forces them to clean up the mess. Despite this, they end up having fun.
- Chris Houghton as Cricket Green, Love singer, Blue man
- Jenna Ortega as Gabriella Espinosa
- Bob Joles as Bill Green, Richard
- Artemis Pebdani as Gramma Alice, Martha
- John Early as Alexander
- Marieve Herington as Smooching woman
- Shane Houghton as Single man, Smooching man
- Keith Silverstein as Waiter, Italian man
- This episode depicts the first time Bill and Alice hear of Cricket's girlfriend. This is strange as he openly mentions it in "Big Resolution".
- Gabriella returns from her trip from Montreal, which she mentioned in "Gabriella's Fella".
- For a moment, The Blue man was jumping of a reference to the two games, Super Mario Bros. and Flappy Bird.
- Alice mentions Ernest in this episode by declaring "Ernest, I'm commin' for ya!". This could be a reference to the character of Fred Sanford from Sanford and Son who had a habit of declaring "I'm commin' Elizabeth, this is the big one!"
- Coincidentally, this episode premieres a day before Valentine's Day (February 14).
- This is the first episode where Tilly Green is absent, save for the intro. However, her voice actress still does additional voices for the episode. This makes Cricket the only character to appear in every episode.
- The movie titles on the marquee include:
- Cold Princess, which is an obvious take on Frozen.
- Tiny Women, which parodies Little Women.
- Cars Go Fast, which parodies The Fast and the Furious franchise.
- Don't Look Back, which shows a man walking away from an explosion, a nod to the famous trope.
- Clowns (But Scary), which parodies It.
- Additionally, this is the first time they do not show a Croblins sequel.
- The blue gentleman from "Mansion Madness" reappears.
- The plot of the episode is similar to the SpongeBob SquarePants episode, "The Chaperone".
- Gabriella's home and bedroom were shown for the first time, and her parents are first mentioned.
- The restaurant they go to, three60, is a reference to the real life spinning restaurants Spindletop in Houston and Tower of the Americas in San Antonio.
- In the scene where Cricket and Gabriella prank the rich people, a man with his wife and her child are sitting at a table, and the man sees his spaghetti, and exclaims " Somebody toucha my spaget!", which is a reference to the meme "Somebody Toucha My Spaghet" from the 1939 Terry Toon The Three Bears. The moment is even animated almost verbatim from the original scene.
- Chris Houghton (Cricket's voice actor) was the singer of the love song over the radio, doing his best Johnny Cash impersonation.
- Moral: Don't put pressure on your child and let them have the fun they deserve.