I just learned that a former student who lives about 300 miles away from me has fallen on very bad times financially due to her financial aid being stopped (bad times as in “dead broke, eating Ramen noodles”). I wanted to send her a gift certificate to a chain restaurant or store so that she can use it a.s.a.p. (she lives in a very small town so mail takes about 4-5 days to get from here to there) but haven’t found any that allow this yet. (Chain restaurants in the town include Ruby Tuesdays, all the major fast-food places and a southern chain called Locos; grocery chains are Winn Dixie, FoodMax and WalMart- I haven’t checked all of them yet, but I was wondering if any sell an online gift card that’s good for brick & mortar stores.)
I once called a restaurant, made reservations for my parents (it was their anniversary, and I lived out of state), and gave them my credit card number and told them to bill me for the meal. They didn’t have any problems with it. Granted, it was a higher end privately owned non-chain restaurant, but I bet some of 'em will do the same for you if you call and ask.
I haven’t found any restaurants or grocery stores that offer on-line gift certificates with on-line delivery. They all require physical delivery of the plastic gift card or certificate to the recipient.
Here’s an alternative: Call a chain restaurant local to your former student, and order a gift card by your credit card. Tell them to hold the gift card for pick-up by the gift recipient.