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My mom is looking for a game she and my aunt used to be obsessed with. I played over their shoulder a lot. This would be in the 2000-2004 range, maybe a little earlier, on one of those websites like pogo.com or Big Fish Games (those are the two I checked because they're the two I remember them using, but I couldn't find this, unless it's gone).
I think it was a "find the connection"-type thing, where you would be given a layout of "cards" with words on them and have to click the ones that had something in common, or maybe they showed you the grouping and you had to name the connection. There were different levels (maybe five in all). In one the cards were stacked in a pyramid of six, and the words just flashed on them briefly and you had to remember where they were. It was timed. I want to say that the logo of either the site or the particular game was a stylized head in profile, possibly with a question mark involved, and if you ran out of time/gave the wrong answer it would react in some way, like changing to an "oh no! Disaster!" expression.