Guy issues ?!?!? should i say somthing?

I have been bestfriend with this one kid. We have legit liked eachother for ever. inbtween gf/ bf we would go out or hook up. Btw we are freshman. Everyone always says ahhh your gonna get married and such. Im not proud of this but i used to not like to be seen with him becuase some people thought he was annoying. He always tells me he likes me , but he also likes 3 other girls. He then expects me to tell him i like him after he told me he loves the world. The worst part is i dont know when to like a person. But whenever he goes out with a girl i get extremely jelous, this is how i know i like him becuase if i didnt then i wouldnt care who he likes. Usualy his gf are from other schools so its not a big deal but 3 days ago he started to go out with a girl from my school. SHould i tell him i like him. I dont want to complicate things. also since he is the sweetest person he will feel bad and then be carefull not to say anything around me, which i dont want becuase we are best friends. He prob the closet friends i have.He might say he likes me back becuase this happened once b4 were he was gooing out with a girl he told me he liked me and i did too, also once when i had a bf. Should i say somthing becuase this is killing me alive, i just want to cry my heart out. I actually feel heartbroken. Please dont comment you only 15 becuase i have never felt like this before and such , thanks so much<3 Plus we sit together on the bus everyday and text every second. I love hanging out with him. I dont wanna be a ***** but should i make him jelous and get with the one person he doesnt want me too, any ideas please!! PLus hey used to text me like 7 times aday now im doing the texting , i dont want to be desperate .