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A main pro, or advantage, of having an inmate pen pal is being able to do something good by communicating with a person who may lack other opportunities for positive social interaction. Many inmates are lonely being closed off from the rest of society and wish to connect with the outside world. One of the major cons, or disadvantages, of writing to an inmate pen pal is the chance that he or she may just want gifts, money or free legal help rather than friendship. Yet a pro is that many prisons prohibit inmates asking pen pals for anything.
Writing to an inmate as part of a group may have the pro of making people feel safer. Church and community groups have projects in which each member writes to an inmate pen pal and a leader oversees all of the communication. Prisons may also monitor pen pal communication, but a con is that this varies depending on budget and area.
Another con of inmate pen pal relationships is that they are controversial in that loved ones of the inmates' victims may feel strongly that these prisoners don't deserve to have and build these social connections. Especially in the cases of victims who were murdered or badly hurt, their families may resent the person convicted of this crime being permitted to receive and send lighthearted pen pal greetings. Inmate dating through Internet pen pal ads is another controversial issue that many people consider a con in case the relationship turns violent or otherwise dangerous after the incarcerated individual's time is served and he or she is released into society.
It could be considered a pro if the prison confirms the crime that the inmate pen pal was convicted of so that the person choosing to write to him or her is aware of it. Not all inmates are untrustworthy or have ulterior motives in communicating with people on the outside. A pro is that if people who are interested in writing to an inmate do so with caution and with the advice of prison or other officials, it could be a chance to really make a difference in another human being's life.
Choosing to write to an inmate who is considered to be dangerous and who shows no remorse for a serious crime can and should be considered as risky as well as a definite con. Having an inmate pen pal who was convicted of a non-violent crime who is remorseful and wanting to change his or her life for the better though can be a real pro. Such inmates who made a mistake for which they regret and have genuinely shown they don't want to harm others may be worth sending good wishes and helpful letters.