i've written to prisoners for a while. I started when I was quite young, writing to juveniles to improve my English, and never really stopped. I've written to death row weirdos and petty crime dindo nuffins.
How you should start, and how I started was by introducing myself, explaining my background and a few of my "favourites". i introduced how i had found him (which not gonna lie, was way easier than just a random guy from writeaprisoner.com), and told him about news he might've missed (not about him). i asked him a few questions about his life (that we already know, but it's nice to not assume), about his family and his interests.
I enclosed a picture of myself (not as a romantic gesture, but as a "name to a face" type thing) and a crossword.
His reply was quite long. He apologised for the delay in replying, as people aren't allowed to send him stamps directly, and he had to purchase a forever global stamp to reply to me and they made him wait for it.
They're drip feeding him letters, but he says it seems most aren't really looking for long term writing. He thinks they're giving him the lower-quality letters first, as he only received mine on the 27th of December.
A lot of people (not just women) have sent explicit photos. He knows this because when they scan in his letters, if something has been censored, they include a note saying why it had been censored and a small description. His favourite censorship note was "penis, erect".
He has been sent at least 3 screenshots of tinder profiles that had been printed and sent with no accompanying note. Someone has signed him up for a subscription to Woman's World. He says there are also women, who he saw during his intake, but they're in a separate part of the facility.
He thanked me for the news update, asked if he could be kept up to date regarding a deal in Israel.
I also mentioned how Apple AI had claimed Luigi had killed himself, and he said he would never do that. He underlined that he would never kill himself.
The prison is "nice enough", it reminds him of one of his friend's dorm rooms, just without carpet. He's not in solitary confinement, but says he's in a single cell. He's discouraged from interacting with other inmates. He swears he saw Sam Bankman-Fried, but wasn't sure since there's a lot of "ugly guys" in there. He mentioned how SBF and Diddy share a cell, and there's a lot of Mexicans, which he wasn't expecting. He had pizza beans for Christmas dinner.
They have been trying to prescribe him with medication, but he prefers to keep his mind clear. He didn't mention if he was taking any.
He sent me back the crossword completed, and said it was great. He asked me to keep sending them. He mentioned his dad loves crosswords, and they used to do the NYT one together.
He apologised for how long the letter was (2 pages of A4), saying he didn't really have a lot to do except read and write. He said he had "enough" in his commissary, and his major expense was stamps. He doesn't miss a lot of snacks from the outside world, but did buy a honey bun for Christmas dessert. It was dry, but he wasn't sure how to complain, if he could.
I've taken out the replies to my personal info and questions he asked me. It was neat at the start, but became a bit untidy towards the end. He signed it "Luigi M

"
I'll probably write again.