How do I give someone an anonymous gift?

Look on the eyeglass site and see if they have gift cards you can purchase.

Despite your good intention, your gift would be likely to embarrass the person receiving it in any case. “I wonder if the giver thought I didn’t know my glasses were broken, didn’t care about that, couldn’t afford to get knew ones or was just too lazy?” On top of that wondering, with the anonymous gift they’d wonder who among their circle of family, friends and acquaintances had done this for them.

So be straight with them. Let ‘em know it’s you, and if it matters, what assumption you made that led you to make the gift. At least that way they won’t be wondering who had these thoughts (or what others they might have had in mind), and they will know exactly what assumption you made.

I’m all in favor of random gifts, and I’m not suggesting that it’s not a good idea that you have – I think it’s a very nice thought on your part – but random gifts of a certain specificity (such as this) would have me wondering “What do you know? What are you thinking? And mostly, who the hell are you?”

Be careful, you may make a spectacle of yourself…yep, I went there

This is one of those situations in which I, personally, would be okay with lying – if your relationship is not a close one. It doesn’t seem to be, from the way you’re writing.

I just received glasses as a gift, actually. Not the prescription, but an expensive frame which suits me very well. The person who gave this to me said they had gotten it for free. I’m pretty sure that’s not entirely true, though she might have paid less than the full price.

Even if she outright lied, I am okay with that. I don’t trust her less – on the contrary, I like that she’s trying to help me while also realising that accepting gifts is not always easy.

If a good friend had been dishonest like that, I would have been disappointed. If you’re talking about a close friend, tell them the truth, and insist that you’ve got the money!

Good for you, by the way!

The gift card option is your best bet. Check with a store close to them, buy them a giftcard that will cover the cost of some glasses and an eye test and perhaps put it in their mailbox?

I think it’s lovely that you’re doing this. I’m sure the person will be very pleased to have new glasses.

Doorbell ditch.

Yup. Giftcards. I would avoid Walmart, however, because it’s doubtful you can restrict their spending there to only an eye exam. Personally, I’m in a small town, so I would probably call around to some eyeglass places and explain to them what I was doing and see if they’d work with me. Perhaps combine this with @longgone white lie and have the store call and tell them someone had submitted their name in a drawing, and they’d won an exam and modest frames.

If you go the giftcard route, you’re going to have to bend over backwards to explain that this is a case of you having the money you want to share and not a pity gift. Again white lying is allowed. Tell them your eccentric aunt gave you a sizable cash Xmas gift with the stipulation that you regift ½ of it. Of course you want to to go some place you might get to see the results.