I personally do this myself. I don't know when it started, and I wouldn't call it a gifted trait, per se, but it seems like small decisions are the worst almost. For me I think the biggest problem is that it's always like I'm "missing" the other choice if I don't choose it -- for example, if I eat the sandwich, would I wish I had had pizza? What if I don't eat pizza again for a while? What if....? It's not like I get anxious over it or anything; it's just more like, "Well, but I COULD...".
I think what works best is either saying " We had x yesterday so let's have y today", or helping to reframe the decision by reminding him either option will work, maybe making a list of pros and con's if it's a big decision. My mother always told me it's not a lifetime decision. At least, ice cream isn't.
