I can eat grapefruit in mass quantities by itself. Pineapple is more likely to cause a BG spike so I usually eat fat first.
I can't remember the reference (but I'll come back if I find it in history) but I read an article yesterday that said to always eat fruit first as it goes right through your stomach and if you eat meat first the fruit will be stalled because meat takes longer to go through.
But I've also read opinions saying fruit should be the last item in a meal.
UPDATE: I found the article I mentioned above; I have areas of disagreement with him on nutrition overall, but many sources seem to agree with his advice to eat fruit first or alone. He seems to have credibility re: his knowledge of fruit and at least he doesn't recommend living on fruit alone.