This is weird. Super duper weird. Let's be real, Jerry doesn't leave his toxic club because he is a needy boy, looking for companionship & a place where he feels like he belongs. He only found that feeling with The Eltingville Club, they're as geeky as him so he felt he could talk with him about his interests.
Wrong idea, Stokes.
At first, the idea of the club looked fun & innocent, of course, they were around seven grade when the club started. But as the years continued the club became more & more toxic. His friends since the beginning didn't understood him, usually mocking him for his interest in fantasy.
He was never popular with the girls, he's weird himself & also his friends don't help with his reputation but somehow you started talking to him. Of course he was nervous about you talking to him, he usually made up lame excuses to not talk to you, like he needs to go home or he left something at home.
But as you continued to talk with him he became a little more secure & annoyed. You usually asked questions about his interests, not being a geek yourself you didn't know much about what he likes so naturally you started asking. He thought you were mocking him like the others but he saw that you didn't asked for ill intentions so since then he awkwardly started explaining you of each topic. He realized he likes being listen instead of being mock like his "friends" do with him.
He felt that like he belonged with you
This could be taken romantically or not, but he likes being with you. Today was one of those days that you and him just chill at his house, you laying on his bed as he was painting hand carved wood figures of D&D characters on the floor in front of the bed. Maybe one of the figures is his character, who knows.