Another technical Q: is there a way to verify that a letter was, in fact, delivered to an inmate and not sitting somewhere undelivered in an office?
Not really. Usually the only way to find out is when the inmate writes back.
Be sure to find out what the rules are for the specific prison system, as they can be incredibly picky. In my state (Kansas), for example, the envelope MUST have your first and last name and a valid (or at least valid-appearing) return address on the outside; it can be a post office box or similar, but an envelope without a sender’s name and address will not be delivered. Neither will an envelope that weighs more than one ounce, so roughly four or five sheets of paper. Your state may well have different rules.
Some states do have an email option, usually a commercial provider such as JPay or Access Corrections, but it’s not free
OK thanks, does it have to be real name or can we use an alias? (along with PO box)
The prison system here wants it to be the real name (whether that’s what they get is less clear, but they do check to be sure it at least plausibly appears to be real).
However, this is really dependent on the individual state systems.
I had a brother, now deceased, who spent a good share of his life behind bars. He told me about writing to women. All the cons do it. Many of them have several they correspond with. They will wonder if the writer has a friend, because there is this guy in jail who gets no visitors and hardly any letters. So maybe you write to the friend, or you have a friend who will write (even though the guy is already writing to several.)
They all have a sad story, and they usually have four or five options of women to use when they get out. So if you write, be extremely cautious of revealing any identifying information. My brother was quite a sweet-talker, but he’d stay with someone only until he found another sucker.