SourPatch's cup-learning hack:
I’ve been teaching my 14 month-old to drink with a cup all by himself (crazy me, didn’t think to introduce him to a cup until he was past one year old). He’s adept at drinking without spilling if someone else is holding the cup, but I wanted to help him learn to drink independently. I have been filling a Dixie cup just enough to coat the bottom of the cup and set it next to him at the dinner table. He can get his hand around the cup easily enough and is able to bring it to his lips without spilling anything. I usually change the cup after every third drink (I put a small stack at the dinner table just for that reason) or when he squeezes the cup out of shape. I just keep refilling his cup as needed. He has become adept at drinking this way and we’re working on increasing the amount of liquid in his cup. I like this because he can’t break the cup by throwing it and he doesn’t spill any on himself (if he does, it's like a drop or two). He loves drinking with a cup just like the adults and has learned to pick up and lay down the cup gently. Best of all, there’s no cleanup afterwards.