Re: After asking sim on a date the game endlessly asks to "Pick a season to play in"

@VibingLemon  As a test, please try playing in a clean user folder.  Move the entire Sims 4 folder out of Documents > Electronic Arts and onto your desktop, and when you launch the game, a clean folder will spawn with no content.  (Your saves and other content will be intact in the folder you moved but temporarily not read by the game.)  Don't add anything to the new folder yet; just start a new save and see whether the problem recurs.

If the problem is gone, try moving one of your existing saves to the new folder, but no other content yet.