Thanks. I had thought a while back that the crane game might have been what I was missing - but for some reason every time I tried talking to the cow, he always just told me to let him know when I wanted to play, so I thought maybe I didn't have enough money.
I can't remember if I ever actually tried speaking to him twice in a row until just now when you reminded me of it.
I can tell I'm going to be facepalming a lot playing this if that's how I started lol