I've done this with meds from my doctor. Like, 3 years ago I stopped taking muscle relaxers for migraine prevention, then I recently pulled my back. I didn't want to pay a copay just to get more, so I did a refill request with my pharmacy.

Sure enough, they rubber-stamped the request.

I doubt they even know what Venmo is. They don't make decisions about or personally handle transactions with small amounts of money.