There is this guy I went to school with in kindergarten that I'll call Ryan for the sake of him. We "dated" in kindergarten and we would always play like we were getting married on the play ground. We continued to "date" in second grade, fifth grade, and seventh grade. All those times I felt feelings for Ryan, but I guess you would just call that puppy love. Well in 8th grade we dated once again because it was getting near Valentines day and my friends kept egging me on to date him just to get a gift. Well I did and I felt awful about it. I didn't have the same feelings for him as he did me. It came Valentines day and I didn't know what to do. He gave me this big gift of several items and my response to it was that I didn't feel the same way about him as he did about me. It broke his heart and seeing him that sad broke mine. He wanted me to keep the gift even though we weren't dating. I did. My friends all took something for themselves, some "friends" they were.
Anyways, here we are both out of high school. He texted me about two months ago and told me he still likes me. Well we are still texting now but I made it clear to him that I couldn't date right now because I had to concentrate on school. He agreed to just be friends. Now I kinda think I may like him now, but honestly I have no idea. I don't want to hurt him again. Plus, my dad and his side of the family doesn't like him and his family and I'm afraid my mom and her side of the family will pick at me for dating someone I dated in kindergarten. I know my friends will aggravate me too for dating someone I had dated in kindergarten. I'm just not sure what to do because like I said I don't want to hurt him. He's a great guy and deserves the best. I need help and I'm open to any responses.
...for the 2nd time this year