jailbird

I met a guy in May of 2021 and we hooked up immediately. I became clingy, waaay too clingy and he was not interested. He explained to me he just wanted to be friends. Even said I wasn’t his type. We never hooked up again.

I was LOVESICK. Blowing up his phone, wondering/asking why, real embarrassing stuff.
He did things like invite me to hangout and when im there tries to hook me up with his friend.
Sent me a naked picture “as a joke”
Shows up where I am hanging out and flirts with my friend/other girls around.
In a way he bullied me a little. This went on for a few months.

Then for 6 months I went through a really tough time and we didn’t see each other anymore but talked on the phone once or twice a week and he was very supportive and a great friend.

Fast forward, now he is in jail. I have been sending him a little money for food and buying around 20 minutes of phone time a week for the last month.
He has started to call more and will call multiple times if I don’t answer. He also asked me to send him pictures of me. So I let him know “I think you’re feeling this way because you are in jail right now and lonely and im the only one here for you but it will change when you get out so stop” he says we don’t know whats going to happen and hes attracted to my loyalty to him.

Am I going to get my heart broke if I let this relationship happen???
Do you think he really could like me??