Speaking from a wide latitude of experiences, particularly that of a prison physician, I’d say: Since you haven’t had an ongoing current relationship with her, it is best to not restart one with her now.
YMMV, typical outcomes may be different from yours.
Yes, I know, what I am saying that in general, unless the person is a blood relative, you should not respond to letters from prison.
If you want to make her feel better see if you can figure a way to send her a letter from within another prison – “Yeah, me too…”
I assume you’ve never been in a relationship with a hot cutie with significant problems then. The hotness and cuteness get old real fast.
I’m not sure I’d read evil intent into the letter, which might just be written to connect to people on the outside, but I’d still not answer.
Not to mention said hot cutie may not exactly be as hot and cute as you remember, after (say) 5 years of doing meth heavily. 
What does she look like?
[del]Is she hot?[/del]
Just say no, bro.
Get a PO Box.
Yeah, conjugal visit sex. That is happening!
Just to add. . . when I read this title, I heard it as “Ross” from “Friends.” Don’t know if you meant it that way.
The aspect of incarceration isn’t really relevant: in the vast majority of cases, re-establishing contact with exes is a bad idea.
*You must not seek to add
To what you have, what you once had;
You have no right to share
What you are with what you were.
No one can have it all,
That is forbidden.
You must learn to choose between.
One happy thing is every happy thing:
Two, is as if they had never been.*
You’re just as romantic as hell, aren’t you?
A more charitable way of looking at it: Being in prison is probably boring as hell. Maybe she’s writing to everyone she used to know because she just wants a pen pal to pass the time. I definitely think it would not be a good idea to get too emotionally or financially involved with a convict, but it might not be bad to send her a letter trying to give her some encouragement to try to get her life back on track after she gets out.
This sounds like the road to hell being paved with good intentions to me. Good Luck. I realize that this isn’t a poll, but I vote ‘No’, anyway.
Prisoners can get very lonely, so any type of communication is often valued greatly. Letters are good as gold to some people that never get visits year after year. Especially at Christmas, it’s even worse.
Whether you contact her is your choice, but play it safe, get a PO box, and write to her and only give her the PO box address. That is assuming she doesn’t know where you live now.
Well…if it was just a question of her showing up wanting sex, I’d probably lose all sense and encourage her to do so once she’s released, though I have no idea what she looks like nowadays…it’s been five years. Was she a hot number back then? Words can’t describe. Did we have a great sex life? Don’t even get me started.
Seriously though, I’d be more worried about my wallet disappearing or my car mysteriously vanishing than I would about sexual gratification.
Even more seriously, I remember her when she was drug-free and quite the humorous ranconteur. I guess part of my problem is that I’m having trouble reconciling my “good” memories of her from previous years with the reality of what she’s most likely like now. I sit here and think, well, writing her a letter might not be a bad idea…but then I remember that I broke up with her for a reason. I was getting off of dope and moving on with my life and she had no interest whatsoever in joining me. The fact that she’s in prison for burglary shows she evidently kept up with her bad habits.
Maybe she’s turning over a new leaf? Who knows. The one thing that the arrival of this letter has taught me is: I probably still have some residual feelings left for her. I just have to address those feelings responsibly.
Lavendarviolet and Markxxx have the right of it IMO. People in jail tend to write a lot more letters than they do outside. Once she’s out she probably won’t contact you because she won’t have hours to fill up. Stamps don’t cost much. Send commissary money if you want but I’d wait and see if she asks for anything first.
Thats awesome.
I’d probably ask her to leave me alone.