He isn't 12. He is 14. I'm 17. It's the age difference between a freshman and a senior. I do regret dating him and I wouldn't date someone younger than me again, but I don't hate myself for talking to someone younger than me 3 years ago. I knew when I was 14 that treating people in certain ways was damaging. I knew if I was manipulating someone - intentionally or unintentionally. I never held any form of power over him due to my age. Ever. Literally not even for a second. If he seemed in any way like a kid, in looks, behavior or anything else, I wouldn't have talked to him because it would've weirded me out. I was kind of weirded out at first, but at that point we were already really close friends. When we started talking, I hadn't dated anyone. Hadn't had a job before, hadn't drove, etc. I was also a kid. When we started talking, we had both lost close friendships and related very closely to one another. For at least 2 years I felt like he was the only person who really understood my feelings or knew what I was going through. There are way, way more 14 year olds who have had more life experience than I have, even now. Do I think at some point I emotionally outgrew him? Yes, absolutely, hence us no longer talking, but at one point he also began emotionally backpedaling and that's a factor in the gap in our compatibility as well. There was only a significant difference in our emotional maturity when my self esteem begun improving within the last 5 months. Us talking at all was about our friendship first the entire time. If we hadn't liked each other at one point we would still have the same issue (as our mutual friends have felt equally alienated by it). It seems really silly to me to think of someone differently due to age when you're on the level of emotional maturity, life experience, etc and are within the same age bracket (in regards to puberty). When we first started talking, and for at least until 5 months ago, we were on the same level in all of those things. The biggest difference was that I knew a few more years of algebra. If you think all of that is simply due to his age, I understand that, but that wasn't necessarily what I came on this website for and I don't necessarily agree. I have a feeling that my situation wasn't entirely the same as yours. I might think differently in a few years, I doubt it but maybe, but that doesn't change that that wasn't what I needed to talk about here. If you would like to be more harsh, by all means go ahead but it seems rather unhelpful for me and maybe frustrating for you.