I haven’t read the replies, only your thread introduction. So, my apologies if what I say has been already said.
Jesyka, from this and other posts by you. I got a thought. Maybe I’m wrong.
That’s why I’m gonna ask you a question. Since I think that I’m now have a better picture of you.

Is it possible that for your past, having social anxiety, you didn’t have many social experiences and you feel the need to experiment (in the good sense) testing yourself and testing to know better about where different people may be coming from? That’s why you are not still so picky. Because you are opening you up to experience whatever possibility to interact. Because you need to live this learning now.
Am I wrong?

As for the guy. Well, when a guy send you pictures too often, there are many possibilities that he wants receive pictures of you. I understand that you always give the benefit of the doubt to people. If you are not interested at having some kind of relationship with this guy, I wouldn’t contact him. You already know where he’s coming from.