Choosing to be a pen pal to a prisoner is a selfless act. Although these men and women have been convicted of crimes, they are still people and they still need human contact.
In your first letter be upfront about what you are expecting from this relationship. If you are only looking for friendship- let them know upfront. Also let them know how often they can expect to hear from you.
Don't ask questions about the crime they have been convicted of. Be encouraging and upbeat in your letters. Prisoners are lonely and this will help them to feel like someone cares about them.
While it is ok to write to more than one prisoner in different facilities, never write to multiple prisoners in the same place. This can cause rivalries and ultimately problems.
Inevitably a prisoner is going to ask you for money. Do NOT send them any of significant amount. If you want to help them with legal fees, sending the money directly to the attorney is your best bet.
If you choose to send a gift to your pen pal make sure that it is on the prison's approved list. Things like magazines can only come from the publisher to the inmates.
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