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We did cupcakes for our wedding. We had the option between normal sized cupcakes and large cupcakes and went with the large. We had a guest list of ~50 people and ordered 65 cupcakes, in case some people wanted extras. If we had done the normal sized cupcakes, I would've gone with 1.5 per person. We just went with chocolate and vanilla flavors so I wasn't too concerned about people taking more than one (also, they were huge cupcakes). We ended up with about 20 leftover.
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