The_Postmaster wrote:
. . . I think I need to make it seem natural, like I've done it a hundred times. . .
Yes, you want to do it with a light touch. You want it to seem like you're not investing that much into it, by at first, not investing that much into.
Ideally, a relationship kind of ping pongs back and forth as each person generally invests more over time.
Maybe be a low-key leader? Pick an event you might be interested in, ask three other people. If all three say no, that's fine, the baseline is that not enough people are interested in the event. If one says yes, the event is a question mark, see if you can get more. If two or three say yes, it's a winning event.