My Prisoner Pen Pal

So I have prisoner pen pal, BUT I have known here for most of my life. He was my first love way back when I was 13. He was a very sweet boyfriend, probably the best boyfriend I have had to date. Back then, boys use to give flowers and buy gifts. He even baked a cake for me for my 14th birthday! They dont make 'em like they use to.

Anyway, his life has taken a different turn than mine and he has been in and out of jail and prison for most of his adult life. Although our "love" relationship ended well before he started getting into trouble, I still remained a friend to him. He has been writing me on occasion from prison and of course in his letters, he likes to reminisce about when we were together... and I dont mind it because I figure, he has a lot of time on his hands and he is going to write about better times, i.e. when we were in puppy love. Also our letters are pretty candid, discussing love, politics, relationships, current events, etc. But in his last letter to me, he spoke about a woman he has met and his plans to be with her once he is released next year... Of course I had to ask him how HE got a woman while he has been incarcerated but I was glad to hear this too (because I didn't want him to get any ideas about us). Well.... he also broached the subject that I was afraid he would... which was would I (or my girlfriends) consider a "regular"man like himself as a potential mate-- not college educated, someone who has made some mistakes (i.e., been locked up) BUT is a hard worker, has dreams, will treat me well, etc.... You know a regular "Joe the Plummer"...

Well the dilemna for me isn't whether I should consider a man like him... I know the answer to that question, which is an honest "No". And I know my girls would say in unison "Hell No!". But the real question for me is how much to sugar coat my answer when I write him back? I could be very evasive, answer a question with a question, you know pull out all my psychologist tricks or I could say something like "Maybe", but the reality is "Nope, not even a little bit". I never say "never", but I know and most of my girls know their limits. And he is a man that I believe despite his mistakes, tries to be a good man and has the potential to do so... And he will always have a place in my heart because he was the first boy (after my dad of course) that filled it. So with that said, I want to be honest and tell him what the reality as I know it is without being brutally honest. Why kick a dog when he is down, right?