Playing a Prison-Themed Save

Prisoners who are on good behavior are sometimes hired for community service type work like planting trees, picking crops and such. Maybe you could take them to a community garden type lot for extra activities and meeting people. There are also prison restaurants open to the general public which are staffed by inmates for their rehabilitation and skilling process, you could probably run a restaurant or bakery, or a prison shop to sell their crafts. Also, they receive visitors, so you could have a day when you invite other sims to the lot to meet them. It could be their family, friends, lawyer, fans (some criminals do get fans, and have penpals, some even marry this way and married folks can have conjugal visits). If the prisoner is pregnant, they could visit the hospital to give birth. Sometimes prisoners get bad tattoos and scars and try to seduce the prison guard or doctor, or you could get them to try escape by building a secret tunnel under their cell one tile at a time.