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Many years ago I worked with a guy who was very big (probably about 500lbs) in an office setting. Most of the chairs they had simply were too small for him and he had to take the arms off of them to sit in them. Then the shock in them broke pretty soon so they sank to the floor when you sat in them and he had to get a new chair. After going through two chairs, without saying anything to him, the management went out and bought a special chair for him that was rated for someone his size. On his way home when the office was mostly empty they pulled him aside and gave him the chair. They simply told him, "I have a feeling you will be more comfortable in this chair."
He was happy, they were happy and nobody was embarrassed/upset. The next day when a few people notices he had a new chair he was the one that said, "yeah, they got me a fat guy chair and it is very nice."
If it is not a work setting then I guess it would depend. If this person was a friend of mine I would just tell them that the chair might not hold them. If they weren't and they were just someone I saw on a daily basis somewhere I would likely just say nothing, but you could always pass them a note or pass a note to the management of the place and give them a heads up. Maybe they will find this person a better chair.
Just a few thoughts.
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