Are you referring to free dining under the currently active general public offer that expires 12/20?
If this is the offer you are thinking of, and your friend is checking in on 2/21, they are not eligible for the free dining offer for any part of that stay. Their check-in date is not within the promotion dates. They would have to book two separate reservations, check out on 2/25 and check back in. Even then they couldn't get the free dining, because you have to have a minimum three night stay for the offer, and if they checked in on the 25th and out on the 26th that's just a one-night stay.