>>317470406
This. It's called "building rapport", and when you have enough of it, it's the most natural thing in the world to be laughing at something together and then just flat out tell them, "Hey, Anon. What's your discord? Lemme send you X." Where X is something topical you mentioned over the course of your discussion you think they'll find funny or interesting.

Bam! Now you're in their DM's. Send a silly gif (can be anything), and then follow that up with your thesis on War Hammer lore or whatever autistic obsession you feel they can't continue existing without knowing about.