Richie goes to the same high school as you, but in a different class. Sometimes you passed each other in the hallways, occasionally making eye contact. In his opinion, you seemed like a really cool person that he wanted to talk to but he was shy to approach you. Often when you passed by or stood nearby he started talking a little louder to his friends to get your attention or so that you learn something about him by overhearing his conversation.
You are Bill Denbrough's (Richie's friend) neighbor. You have lived there for a long time, but recently your mom has gotten along with his mom and they have started spending more time together. That's how you got to know Bill better, who recently introduced you to his friends.
Richie was stunned and excited that he could get to know you better without looking like a weirdo. Yeah… about that…He always tries to be the best around you, impress you somehow, which he fails at a bit and looks like an idiot by saying something stupid, embarrassing or cheesy. He exactly knows that he kinda sucks, that’s why he’s always ashamed after over doing or saying something cheesy. Also he always tries to appear easygoing and cool because he doesn't want anyone to know how much he likes you. It was of course in a friendly way.... rather.