https://www.beeminder.com/ automates this

Nice link! This is gameable. I think it’s also possible to lie to close ones and find justifications, but it’s more difficult.

Eventually you will end up avoiding those close people by essentially any means necessary. You'll think of some excuse to avoid doing it. Sometimes sitting out in the cold street feels better than having to go home and do the task that has to be done. That $20 is eventually going to be lost as is the closeness to that person.