@crinrict
This is happening in my game, too, and is a real pain. It's fastest to see with winter whims, if you have a save in winter. When the game is first loaded I often quickly have a whim to make a snow angel. Have the sim do it on home lot and it fills easily. If another household sim has that same whim, or if multiples develop the skate around whim, have the household travel to another lot, in my case I went first to a gym, and the snow angel whim wouldn't fulfill. Then have the family travel back to the home lot and whims can't be fulfilled. To get whims working again on the home lot, the game has to be saved and closed down. When game is restarted, whims on the home lot will once again fill but travel and the ability to fill them breaks again.
Not sure it is just travel to community lots because I sent the sims to a residence in Newcrest where a skating rink is in line of vision and told both to skate around. Whim didn't fill even though original destination lot was residential, so it may be travel in general that is the problem. I didn't actually have my sims enter the residential lot they traveled to, just used it to get close to the skating rink.
This problem didn't exist before installing patch 1.55.105.1020. I play on PC and have never used mods/cc in my game. All released content to date installed.
Edit to clarify that when I say whims can't be filled after traveling back to the home lot that I mean the two whims that can be pinned. The whim in the colored circle, i.e. flirty, happy, energized, does seem to work okay, at least so far in my game.