|Time||4:30 pm - 11:00 pm|
|Trophy|| Pinky's Photo|
Big Teddy Bear
|Mission|| Race the Vale*|
- "Jimmy, I'm really starting to like you."
- — Pinky Gauthier
Carnival Date is a storyline mission in Chapter 2.
Pinky is standing outside the movie theater. As Jimmy walks up, she begins berating him for having been three minutes late for their date. Jimmy, who didn't realize they had a date, is confused until Pinky realizes it was Derby Harrington who she had the date with. She takes Jimmy's flowers. As Derby is a no-show, Jimmy offers to take her out in his place, and Pinky asks him to meet her at Billy Crane's Traveling Carnival.
Get to the Carnival and buy an entrance ticket. A short cutscene plays where Pinky runs up to greet Jimmy. Pinky asks him to win her a teddy bear. The bear can be purchased from the prize tent for 10 tickets. The tickets are earned by playing the various games around the Carnival.
Jimmy and Pinky hold hands as they walk through the carnival. If Jimmy and Pinky cross the paths of a girl who Jimmy has already kissed, that girl will become jealous and either hit Jimmy or get in a hair pulling match with Pinky. Pinky may also be harassed by the Greasers if Jimmy runs across any of them.
The two of them can ride the rides together, although this doesn't contribute towards completing the mission. Pinky freaks out if Jimmy tries to take her to the Freak Show.
Each time Jimmy passes a game, Pinky asks him to try it. It doesn't matter which games he plays, so long as he wins 10 tickets. If he already has ten prize tickets, he doesn't have to play the games, he just has to go straight in and get the bear.
Once he has purchased the bear, the mission ends. If he hasn't bought the bear by 1 a.m., he fails the mission.
- Dan and Kirby have unused dialogue for this mission. They were supposed to either pick a fight with Jimmy or challenge him in a carnival game. Despite being scrapped, both of them can still be seen walking past Jimmy and Pinky, sometimes armed with baseball bats.
- In Scholarship Edition some audio files during this mission, namely, Pinky telling Jimmy to pick up the teddy bear and thanking him for the date, are corrupted and thus sound distorted.
- At the prize tent, all of the other prizes will say that they are out of stock, so Jimmy can't buy anything besides the bear.