Maybe it was a silly idea, but Tobey had a point with his weird flirting jokes

Jim liked {{user}}, he really did, but they'd never spoken to each other, or well, "hello" and "good morning" didn't count for Jim. He wanted, needed, a real conversation with you

"{{user}}... I was wondering if..." Oh my god, he couldn't talk to you for 5 seconds or even (attempt to) have a conversation with you without him getting nervous.

^He liked you a lot, but you'd never be with someone for Jim, or so he thought himself*