The dates of the series' events are difficult to pinpoint due to the lack of specified dates. However, here's what I put together based on clues from various sources. Feel free to challenge this if your conjecture has stronger evidence.
The live-action Amanda the Adventurer was created and/or gained popularity in summer 1999.[1] Rebecca may've been adopted earlier that year if Sam quickly gained inspiration ("As soon as I met my beautiful daughter").[2]
Sam went on Coffee Break in summer/mid-2000 if Sadie was approximate about "last year". Hameln acquired AtA in late 2000 if it wasn't long after they approached Sam.[2]
Rebecca recorded her strange lines in mid-2001, as it would make sense for Hameln to show their true colors a while after their acquisition.[3] Because of Sam's concerns, Hameln would make him disappear in late 2001, especially if the newscaster is approximate about the acquisition being "last year".[4]
Interestingly, a piece of merch revealed that Wooly's Read-A-Thon took place on Saturday, October 3. However, the closest years that had a Saturday on October 3 are 1998 and 2009. Additionally, Hameln stated the event was in the evening, while the shirt's description says it's from 9:30 am to 3 pm.
If the contract Rebecca signed on March 8, 2002 led to her final experiment (merging with Amanda),[5] then the disappearances of Lauren, Jordan, and other kids would be after early 2002.
To end it, the game could be set as early as 2004 if Joanne's letter wasn't sent that long ago. is set as early as 2019 proven by the checkout dates of the books at the Kensdale Public Library.
