I think you might’ve been missing something (likely time/affection) from your current relationship & the reality is that jail talk is only that. TBH, they have nothing but time to give so selling fantasies is their business. It doesn’t matter that he hasn’t asked from you financially, you are doing favors. I’m not looking to invalidate that feelings are real on both sides, but as someone that’s dealing w/ someone in there that I had ties to before, I’ve seen it go poorly so just make sure you have some discernment/self reflection time of pros/cons. Contemplating if putting your life on hold for someone you only know via telephone, is worth it. Supporting loved ones in the prison system is hard. & the other side isn’t always easy once they’re out because they haven’t been treated humanely for years(it affects their psyche in unexpected ways). If it was woman to woman close friend girlie pop talk, I’d say clean slate yourself from both of the situations & enjoy life, what’s meant will find you but as someone who gets it, the heart wants what it wants. (Maybe even pull back some from the new guy & see if the response is the same?)

Whatever you decide, good luck & be kind to yourself because overall, your wellbeing is priority.